diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/common/index.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/common/index.ts
index cfb4987862535..81b8a6ac56292 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/common/index.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/common/index.ts
@@ -51,3 +51,5 @@ export { DEFAULT_LANGUAGE_OPTION, LANGUAGE_OPTIONS } from './ui_settings/languag
 export { isSupportedConnectorType } from './connectors';
 
 export { ShortIdTable } from './utils/short_id_table';
+
+export { KnowledgeBaseType } from './types';
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/common/types.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/common/types.ts
index bd1a284b0d363..68595e457a355 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/common/types.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/common/types.ts
@@ -84,6 +84,7 @@ export interface KnowledgeBaseEntry {
   doc_id: string;
   confidence: 'low' | 'medium' | 'high';
   is_correction: boolean;
+  type?: 'user_instruction' | 'contextual';
   public: boolean;
   labels?: Record<string, string>;
   role: KnowledgeBaseEntryRole;
@@ -92,13 +93,26 @@ export interface KnowledgeBaseEntry {
   };
 }
 
-export interface UserInstruction {
+export interface Instruction {
   doc_id: string;
   text: string;
-  system?: boolean;
 }
 
-export type UserInstructionOrPlainText = string | UserInstruction;
+export interface AdHocInstruction {
+  doc_id?: string;
+  text: string;
+  instruction_type: 'user_instruction' | 'application_instruction';
+}
+
+export type InstructionOrPlainText = string | Instruction;
+
+export enum KnowledgeBaseType {
+  // user instructions are included in the system prompt regardless of the user's input
+  UserInstruction = 'user_instruction',
+
+  // contextual entries are only included in the system prompt if the user's input matches the context
+  Contextual = 'contextual',
+}
 
 export interface ObservabilityAIAssistantScreenContextRequest {
   screenDescription?: string;
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/public/index.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/public/index.ts
index 2e604b59fc7ab..7e7ed20de18e3 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/public/index.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/public/index.ts
@@ -78,6 +78,8 @@ export type {
   ShortIdTable,
 } from '../common';
 
+export { KnowledgeBaseType } from '../common';
+
 export type { TelemetryEventTypeWithPayload } from './analytics';
 export { ObservabilityAIAssistantTelemetryEventType } from './analytics/telemetry_event_type';
 
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/public/types.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/public/types.ts
index 8480af2e02327..c00cf4805ff8d 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/public/types.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/public/types.ts
@@ -18,7 +18,7 @@ import type {
   Message,
   ObservabilityAIAssistantScreenContext,
   PendingMessage,
-  UserInstructionOrPlainText,
+  AdHocInstruction,
 } from '../common/types';
 import type { TelemetryEventTypeWithPayload } from './analytics';
 import type { ObservabilityAIAssistantAPIClient } from './api';
@@ -68,7 +68,7 @@ export interface ObservabilityAIAssistantChatService {
         };
     signal: AbortSignal;
     responseLanguage?: string;
-    instructions?: UserInstructionOrPlainText[];
+    instructions?: AdHocInstruction[];
   }) => Observable<StreamingChatResponseEventWithoutError>;
   getFunctions: (options?: { contexts?: string[]; filter?: string }) => FunctionDefinition[];
   hasFunction: (name: string) => boolean;
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/functions/summarize.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/functions/summarize.ts
index ff14f5a3d3db3..8865861d81f45 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/functions/summarize.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/functions/summarize.ts
@@ -5,6 +5,7 @@
  * 2.0.
  */
 
+import { KnowledgeBaseType } from '../../common/types';
 import type { FunctionRegistrationParameters } from '.';
 import { KnowledgeBaseEntryRole } from '../../common';
 
@@ -66,13 +67,14 @@ export function registerSummarizationFunction({
       signal
     ) => {
       return client
-        .createKnowledgeBaseEntry({
+        .addKnowledgeBaseEntry({
           entry: {
             doc_id: id,
             role: KnowledgeBaseEntryRole.AssistantSummarization,
             id,
             text,
             is_correction: isCorrection,
+            type: KnowledgeBaseType.Contextual,
             confidence,
             public: isPublic,
             labels: {},
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/routes/chat/route.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/routes/chat/route.ts
index f1758c1583f71..73d8b0d1354e0 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/routes/chat/route.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/routes/chat/route.ts
@@ -41,17 +41,15 @@ const chatCompleteBaseRt = t.type({
         }),
       ]),
       instructions: t.array(
-        t.union([
-          t.string,
-          t.intersection([
-            t.type({
-              doc_id: t.string,
-              text: t.string,
-            }),
-            t.partial({
-              system: t.boolean,
-            }),
-          ]),
+        t.intersection([
+          t.partial({ doc_id: t.string }),
+          t.type({
+            text: t.string,
+            instruction_type: t.union([
+              t.literal('user_instruction'),
+              t.literal('application_instruction'),
+            ]),
+          }),
         ])
       ),
     }),
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/routes/functions/route.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/routes/functions/route.ts
index 52be33c2a372d..fae7077953699 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/routes/functions/route.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/routes/functions/route.ts
@@ -41,7 +41,7 @@ const getFunctionsRoute = createObservabilityAIAssistantServerRoute({
         screenContexts: [],
       }),
       // error is caught in client
-      client.fetchUserInstructions(),
+      client.getKnowledgeBaseUserInstructions(),
     ]);
 
     const functionDefinitions = functionClient.getFunctions().map((fn) => fn.definition);
@@ -51,9 +51,9 @@ const getFunctionsRoute = createObservabilityAIAssistantServerRoute({
     return {
       functionDefinitions: functionClient.getFunctions().map((fn) => fn.definition),
       systemMessage: getSystemMessageFromInstructions({
-        registeredInstructions: functionClient.getInstructions(),
+        applicationInstructions: functionClient.getInstructions(),
         userInstructions,
-        requestInstructions: [],
+        adHocInstructions: [],
         availableFunctionNames,
       }),
     };
@@ -111,6 +111,7 @@ const functionSummariseRoute = createObservabilityAIAssistantServerRoute({
       text: nonEmptyStringRt,
       confidence: t.union([t.literal('low'), t.literal('medium'), t.literal('high')]),
       is_correction: toBooleanRt,
+      type: t.union([t.literal('user_instruction'), t.literal('contextual')]),
       public: toBooleanRt,
       labels: t.record(t.string, t.string),
     }),
@@ -129,17 +130,19 @@ const functionSummariseRoute = createObservabilityAIAssistantServerRoute({
       confidence,
       id,
       is_correction: isCorrection,
+      type,
       text,
       public: isPublic,
       labels,
     } = resources.params.body;
 
-    return client.createKnowledgeBaseEntry({
+    return client.addKnowledgeBaseEntry({
       entry: {
         confidence,
         id,
         doc_id: id,
         is_correction: isCorrection,
+        type,
         text,
         public: isPublic,
         labels,
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/routes/knowledge_base/route.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/routes/knowledge_base/route.ts
index 6dfbde7654039..6bb024b913cde 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/routes/knowledge_base/route.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/routes/knowledge_base/route.ts
@@ -13,7 +13,12 @@ import { notImplemented } from '@hapi/boom';
 import { nonEmptyStringRt, toBooleanRt } from '@kbn/io-ts-utils';
 import * as t from 'io-ts';
 import { createObservabilityAIAssistantServerRoute } from '../create_observability_ai_assistant_server_route';
-import { KnowledgeBaseEntry, KnowledgeBaseEntryRole } from '../../../common/types';
+import {
+  Instruction,
+  KnowledgeBaseEntry,
+  KnowledgeBaseEntryRole,
+  KnowledgeBaseType,
+} from '../../../common/types';
 
 const getKnowledgeBaseStatus = createObservabilityAIAssistantServerRoute({
   endpoint: 'GET /internal/observability_ai_assistant/kb/status',
@@ -60,6 +65,64 @@ const setupKnowledgeBase = createObservabilityAIAssistantServerRoute({
   },
 });
 
+const getKnowledgeBaseUserInstructions = createObservabilityAIAssistantServerRoute({
+  endpoint: 'GET /internal/observability_ai_assistant/kb/user_instructions',
+  options: {
+    tags: ['access:ai_assistant'],
+  },
+  handler: async (
+    resources
+  ): Promise<{
+    userInstructions: Array<Instruction & { public?: boolean }>;
+  }> => {
+    const client = await resources.service.getClient({ request: resources.request });
+
+    if (!client) {
+      throw notImplemented();
+    }
+
+    return {
+      userInstructions: await client.getKnowledgeBaseUserInstructions(),
+    };
+  },
+});
+
+const saveKnowledgeBaseUserInstruction = createObservabilityAIAssistantServerRoute({
+  endpoint: 'PUT /internal/observability_ai_assistant/kb/user_instructions',
+  params: t.type({
+    body: t.type({
+      id: t.string,
+      text: nonEmptyStringRt,
+      public: toBooleanRt,
+    }),
+  }),
+  options: {
+    tags: ['access:ai_assistant'],
+  },
+  handler: async (resources): Promise<void> => {
+    const client = await resources.service.getClient({ request: resources.request });
+
+    if (!client) {
+      throw notImplemented();
+    }
+
+    const { id, text, public: isPublic } = resources.params.body;
+    return client.addKnowledgeBaseEntry({
+      entry: {
+        id,
+        doc_id: id,
+        text,
+        public: isPublic,
+        confidence: 'high',
+        is_correction: false,
+        type: KnowledgeBaseType.UserInstruction,
+        labels: {},
+        role: KnowledgeBaseEntryRole.UserEntry,
+      },
+    });
+  },
+});
+
 const getKnowledgeBaseEntries = createObservabilityAIAssistantServerRoute({
   endpoint: 'GET /internal/observability_ai_assistant/kb/entries',
   options: {
@@ -130,13 +193,14 @@ const saveKnowledgeBaseEntry = createObservabilityAIAssistantServerRoute({
       role,
     } = resources.params.body;
 
-    return client.createKnowledgeBaseEntry({
+    return client.addKnowledgeBaseEntry({
       entry: {
         id,
         text,
         doc_id: id,
         confidence: confidence ?? 'high',
         is_correction: isCorrection ?? false,
+        type: 'contextual',
         public: isPublic ?? true,
         labels: labels ?? {},
         role: (role as KnowledgeBaseEntryRole) ?? KnowledgeBaseEntryRole.UserEntry,
@@ -192,6 +256,7 @@ const importKnowledgeBaseEntries = createObservabilityAIAssistantServerRoute({
       doc_id: entry.id,
       confidence: 'high' as KnowledgeBaseEntry['confidence'],
       is_correction: false,
+      type: 'contextual' as const,
       public: true,
       labels: {},
       role: KnowledgeBaseEntryRole.UserEntry,
@@ -206,6 +271,8 @@ export const knowledgeBaseRoutes = {
   ...setupKnowledgeBase,
   ...getKnowledgeBaseStatus,
   ...getKnowledgeBaseEntries,
+  ...saveKnowledgeBaseUserInstruction,
+  ...getKnowledgeBaseUserInstructions,
   ...importKnowledgeBaseEntries,
   ...saveKnowledgeBaseEntry,
   ...deleteKnowledgeBaseEntry,
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/chat_function_client/index.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/chat_function_client/index.ts
index 0b0f202e703cd..fc90a4e0caa3d 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/chat_function_client/index.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/chat_function_client/index.ts
@@ -16,7 +16,7 @@ import type {
   FunctionCallChatFunction,
   FunctionHandler,
   FunctionHandlerRegistry,
-  RegisteredInstruction,
+  InstructionOrCallback,
   RegisterFunction,
   RegisterInstruction,
 } from '../types';
@@ -34,7 +34,7 @@ const ajv = new Ajv({
 export const GET_DATA_ON_SCREEN_FUNCTION_NAME = 'get_data_on_screen';
 
 export class ChatFunctionClient {
-  private readonly instructions: RegisteredInstruction[] = [];
+  private readonly instructions: InstructionOrCallback[] = [];
   private readonly functionRegistry: FunctionHandlerRegistry = new Map();
   private readonly validators: Map<string, ValidateFunction> = new Map();
 
@@ -107,7 +107,7 @@ export class ChatFunctionClient {
     }
   }
 
-  getInstructions(): RegisteredInstruction[] {
+  getInstructions(): InstructionOrCallback[] {
     return this.instructions;
   }
 
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/index.test.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/index.test.ts
index cbe033ed0e4b9..33bd0ab49b1d7 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/index.test.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/index.test.ts
@@ -26,7 +26,6 @@ import { createFunctionResponseMessage } from '../../../common/utils/create_func
 import { CONTEXT_FUNCTION_NAME } from '../../functions/context';
 import { ChatFunctionClient } from '../chat_function_client';
 import type { KnowledgeBaseService } from '../knowledge_base_service';
-import { USER_INSTRUCTIONS_HEADER } from '../util/get_system_message_from_instructions';
 import { observableIntoStream } from '../util/observable_into_stream';
 import { CreateChatCompletionResponseChunk } from './adapters/process_openai_stream';
 
@@ -34,7 +33,7 @@ type ChunkDelta = CreateChatCompletionResponseChunk['choices'][number]['delta'];
 
 type LlmSimulator = ReturnType<typeof createLlmSimulator>;
 
-const EXPECTED_STORED_SYSTEM_MESSAGE = `system\n\n${USER_INSTRUCTIONS_HEADER}\n\nYou MUST respond in the users preferred language which is: English.`;
+const EXPECTED_STORED_SYSTEM_MESSAGE = `system\n\nYou MUST respond in the users preferred language which is: English.`;
 
 const nextTick = () => {
   return new Promise(process.nextTick);
@@ -367,8 +366,8 @@ describe('Observability AI Assistant client', () => {
               last_updated: expect.any(String),
               token_count: {
                 completion: 1,
-                prompt: 84,
-                total: 85,
+                prompt: 46,
+                total: 47,
               },
             },
             type: StreamingChatResponseEventType.ConversationCreate,
@@ -424,8 +423,8 @@ describe('Observability AI Assistant client', () => {
               last_updated: expect.any(String),
               token_count: {
                 completion: 6,
-                prompt: 268,
-                total: 274,
+                prompt: 230,
+                total: 236,
               },
             },
             type: StreamingChatResponseEventType.ConversationCreate,
@@ -442,8 +441,8 @@ describe('Observability AI Assistant client', () => {
                 title: 'An auto-generated title',
                 token_count: {
                   completion: 6,
-                  prompt: 268,
-                  total: 274,
+                  prompt: 230,
+                  total: 236,
                 },
               },
               labels: {},
@@ -573,8 +572,8 @@ describe('Observability AI Assistant client', () => {
           last_updated: expect.any(String),
           token_count: {
             completion: 2,
-            prompt: 162,
-            total: 164,
+            prompt: 124,
+            total: 126,
           },
         },
         type: StreamingChatResponseEventType.ConversationUpdate,
@@ -592,8 +591,8 @@ describe('Observability AI Assistant client', () => {
             title: 'My stored conversation',
             token_count: {
               completion: 2,
-              prompt: 162,
-              total: 164,
+              prompt: 124,
+              total: 126,
             },
           },
           labels: {},
@@ -1609,7 +1608,10 @@ describe('Observability AI Assistant client', () => {
       .subscribe(() => {}); // To trigger call to chat
     await nextTick();
 
-    expect(chatSpy.mock.calls[0][1].messages[0].message.content).toEqual(
+    const systemMessage = chatSpy.mock.calls[0][1].messages[0];
+
+    expect(systemMessage.message.role).toEqual(MessageRole.System);
+    expect(systemMessage.message.content).toEqual(
       EXPECTED_STORED_SYSTEM_MESSAGE.replace('English', 'Orcish')
     );
   });
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/index.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/index.ts
index 4c3527873d01c..293d2da9c04b9 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/index.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/index.ts
@@ -46,12 +46,12 @@ import {
 } from '../../../common/conversation_complete';
 import { CompatibleJSONSchema } from '../../../common/functions/types';
 import {
-  UserInstructionOrPlainText,
   type Conversation,
   type ConversationCreateRequest,
   type ConversationUpdateRequest,
   type KnowledgeBaseEntry,
   type Message,
+  type AdHocInstruction,
 } from '../../../common/types';
 import { withoutTokenCountEvents } from '../../../common/utils/without_token_count_events';
 import { CONTEXT_FUNCTION_NAME } from '../../functions/context';
@@ -159,7 +159,21 @@ export class ObservabilityAIAssistantClient {
     });
   };
 
-  complete = (params: {
+  complete = ({
+    functionClient,
+    connectorId,
+    simulateFunctionCalling,
+    instructions: adHocInstructions = [],
+    messages: initialMessages,
+    signal,
+    responseLanguage = 'English',
+    persist,
+    kibanaPublicUrl,
+    isPublic,
+    title: predefinedTitle,
+    conversationId: predefinedConversationId,
+    disableFunctions = false,
+  }: {
     messages: Message[];
     connectorId: string;
     signal: AbortSignal;
@@ -170,7 +184,7 @@ export class ObservabilityAIAssistantClient {
     title?: string;
     isPublic?: boolean;
     kibanaPublicUrl?: string;
-    instructions?: UserInstructionOrPlainText[];
+    instructions?: AdHocInstruction[];
     simulateFunctionCalling?: boolean;
     disableFunctions?:
       | boolean
@@ -181,26 +195,11 @@ export class ObservabilityAIAssistantClient {
     return new LangTracer(context.active()).startActiveSpan(
       'complete',
       ({ tracer: completeTracer }) => {
-        const {
-          functionClient,
-          connectorId,
-          simulateFunctionCalling,
-          instructions: requestInstructions = [],
-          messages: initialMessages,
-          signal,
-          responseLanguage = 'English',
-          persist,
-          kibanaPublicUrl,
-          isPublic,
-          title: predefinedTitle,
-          conversationId: predefinedConversationId,
-          disableFunctions = false,
-        } = params;
-
         if (responseLanguage) {
-          requestInstructions.push(
-            `You MUST respond in the users preferred language which is: ${responseLanguage}.`
-          );
+          adHocInstructions.push({
+            instruction_type: 'application_instruction',
+            text: `You MUST respond in the users preferred language which is: ${responseLanguage}.`,
+          });
         }
 
         const isConversationUpdate = persist && !!predefinedConversationId;
@@ -208,14 +207,15 @@ export class ObservabilityAIAssistantClient {
         const conversationId = persist ? predefinedConversationId || v4() : '';
 
         if (persist && !isConversationUpdate && kibanaPublicUrl) {
-          requestInstructions.push(
-            `This conversation will be persisted in Kibana and available at this url: ${
+          adHocInstructions.push({
+            instruction_type: 'application_instruction',
+            text: `This conversation will be persisted in Kibana and available at this url: ${
               kibanaPublicUrl + `/app/observabilityAIAssistant/conversations/${conversationId}`
-            }.`
-          );
+            }.`,
+          });
         }
 
-        const userInstructions$ = from(this.fetchUserInstructions()).pipe(shareReplay());
+        const userInstructions$ = from(this.getKnowledgeBaseUserInstructions()).pipe(shareReplay());
 
         // from the initial messages, override any system message with
         // the one that is based on the instructions (registered, request, kb)
@@ -224,9 +224,9 @@ export class ObservabilityAIAssistantClient {
             // this is what we eventually store in the conversation
             const messagesWithUpdatedSystemMessage = replaceSystemMessage(
               getSystemMessageFromInstructions({
-                registeredInstructions: functionClient.getInstructions(),
+                applicationInstructions: functionClient.getInstructions(),
                 userInstructions,
-                requestInstructions,
+                adHocInstructions,
                 availableFunctionNames: functionClient
                   .getFunctions()
                   .map((fn) => fn.definition.name),
@@ -303,7 +303,7 @@ export class ObservabilityAIAssistantClient {
                 functionCallsLeft: MAX_FUNCTION_CALLS,
                 functionClient,
                 userInstructions,
-                requestInstructions,
+                adHocInstructions,
                 signal,
                 logger: this.dependencies.logger,
                 disableFunctions,
@@ -731,7 +731,7 @@ export class ObservabilityAIAssistantClient {
     return this.dependencies.knowledgeBaseService.setup();
   };
 
-  createKnowledgeBaseEntry = async ({
+  addKnowledgeBaseEntry = async ({
     entry,
   }: {
     entry: Omit<KnowledgeBaseEntry, '@timestamp'>;
@@ -772,7 +772,7 @@ export class ObservabilityAIAssistantClient {
     return this.dependencies.knowledgeBaseService.deleteEntry({ id });
   };
 
-  fetchUserInstructions = async () => {
+  getKnowledgeBaseUserInstructions = async () => {
     return this.dependencies.knowledgeBaseService.getUserInstructions(
       this.dependencies.namespace,
       this.dependencies.user
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/operators/continue_conversation.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/operators/continue_conversation.ts
index 237eea9411b23..a06fca2e13278 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/operators/continue_conversation.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/operators/continue_conversation.ts
@@ -28,7 +28,7 @@ import {
   MessageOrChatEvent,
 } from '../../../../common/conversation_complete';
 import { FunctionVisibility } from '../../../../common/functions/types';
-import { UserInstruction } from '../../../../common/types';
+import { AdHocInstruction, Instruction } from '../../../../common/types';
 import { createFunctionResponseMessage } from '../../../../common/utils/create_function_response_message';
 import { emitWithConcatenatedMessage } from '../../../../common/utils/emit_with_concatenated_message';
 import { withoutTokenCountEvents } from '../../../../common/utils/without_token_count_events';
@@ -171,7 +171,7 @@ export function continueConversation({
   chat,
   signal,
   functionCallsLeft,
-  requestInstructions,
+  adHocInstructions,
   userInstructions,
   logger,
   disableFunctions,
@@ -182,8 +182,8 @@ export function continueConversation({
   chat: ChatFunctionWithoutConnector;
   signal: AbortSignal;
   functionCallsLeft: number;
-  requestInstructions: Array<string | UserInstruction>;
-  userInstructions: UserInstruction[];
+  adHocInstructions: AdHocInstruction[];
+  userInstructions: Instruction[];
   logger: Logger;
   disableFunctions:
     | boolean
@@ -204,9 +204,9 @@ export function continueConversation({
 
   const messagesWithUpdatedSystemMessage = replaceSystemMessage(
     getSystemMessageFromInstructions({
-      registeredInstructions: functionClient.getInstructions(),
+      applicationInstructions: functionClient.getInstructions(),
       userInstructions,
-      requestInstructions,
+      adHocInstructions,
       availableFunctionNames: definitions.map((def) => def.name),
     }),
     initialMessages
@@ -325,7 +325,7 @@ export function continueConversation({
               functionClient,
               signal,
               userInstructions,
-              requestInstructions,
+              adHocInstructions,
               logger,
               disableFunctions,
               tracer,
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/operators/get_generated_title.test.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/operators/get_generated_title.test.ts
index ef538ef27bdfd..02f5e5c294466 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/operators/get_generated_title.test.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/operators/get_generated_title.test.ts
@@ -13,7 +13,7 @@ import {
 } from '../../../../common';
 import { ChatEvent } from '../../../../common/conversation_complete';
 import { LangTracer } from '../instrumentation/lang_tracer';
-import { getGeneratedTitle } from './get_generated_title';
+import { TITLE_CONVERSATION_FUNCTION_NAME, getGeneratedTitle } from './get_generated_title';
 
 describe('getGeneratedTitle', () => {
   const messages: Message[] = [
@@ -83,7 +83,7 @@ describe('getGeneratedTitle', () => {
     const { chatSpy, title$ } = callGenerateTitle([
       createChatCompletionChunk({
         function_call: {
-          name: 'title_conversation',
+          name: TITLE_CONVERSATION_FUNCTION_NAME,
           arguments: JSON.stringify({ title: 'My title' }),
         },
       }),
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/operators/get_generated_title.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/operators/get_generated_title.ts
index 2b635c6d0ccf9..23440c30bdcca 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/operators/get_generated_title.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/client/operators/get_generated_title.ts
@@ -14,6 +14,8 @@ import { hideTokenCountEvents } from './hide_token_count_events';
 import { ChatEvent, TokenCountEvent } from '../../../../common/conversation_complete';
 import { LangTracer } from '../instrumentation/lang_tracer';
 
+export const TITLE_CONVERSATION_FUNCTION_NAME = 'title_conversation';
+
 type ChatFunctionWithoutConnectorAndTokenCount = (
   name: string,
   params: Omit<
@@ -59,7 +61,7 @@ export function getGeneratedTitle({
       ],
       functions: [
         {
-          name: 'title_conversation',
+          name: TITLE_CONVERSATION_FUNCTION_NAME,
           description:
             'Use this function to title the conversation. Do not wrap the title in quotes',
           parameters: {
@@ -73,7 +75,7 @@ export function getGeneratedTitle({
           },
         },
       ],
-      functionCall: 'title_conversation',
+      functionCall: TITLE_CONVERSATION_FUNCTION_NAME,
       tracer,
     }).pipe(
       hide(),
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/index.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/index.ts
index eddcb8112f540..c087e5940f0b7 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/index.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/index.ts
@@ -323,7 +323,7 @@ export class ObservabilityAIAssistantService {
     return fnClient;
   }
 
-  addToKnowledgeBase(entries: KnowledgeBaseEntryRequest[]): void {
+  addToKnowledgeBaseQueue(entries: KnowledgeBaseEntryRequest[]): void {
     this.init()
       .then(() => {
         this.kbService!.queue(
@@ -334,6 +334,7 @@ export class ObservabilityAIAssistantService {
               doc_id: entry.id,
               public: true,
               confidence: 'high' as const,
+              type: 'contextual' as const,
               is_correction: false,
               labels: {
                 ...entry.labels,
@@ -364,7 +365,7 @@ export class ObservabilityAIAssistantService {
   }
 
   addCategoryToKnowledgeBase(categoryId: string, entries: KnowledgeBaseEntryRequest[]) {
-    this.addToKnowledgeBase(
+    this.addToKnowledgeBaseQueue(
       entries.map((entry) => {
         return {
           ...entry,
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/kb_component_template.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/kb_component_template.ts
index c28821c3d8517..a4c6dc25d2e57 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/kb_component_template.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/kb_component_template.ts
@@ -38,6 +38,7 @@ export const kbComponentTemplate: ClusterComponentTemplate['component_template']
           name: keyword,
         },
       },
+      type: keyword,
       labels: dynamic,
       conversation: {
         properties: {
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/knowledge_base_service/index.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/knowledge_base_service/index.ts
index 6c62cce3ebdb7..679d59a57dbc8 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/knowledge_base_service/index.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/knowledge_base_service/index.ts
@@ -19,7 +19,12 @@ import {
   INDEX_QUEUED_DOCUMENTS_TASK_TYPE,
   resourceNames,
 } from '..';
-import { KnowledgeBaseEntry, KnowledgeBaseEntryRole, UserInstruction } from '../../../common/types';
+import {
+  Instruction,
+  KnowledgeBaseEntry,
+  KnowledgeBaseEntryRole,
+  KnowledgeBaseType,
+} from '../../../common/types';
 import { getAccessQuery } from '../util/get_access_query';
 import { getCategoryQuery } from '../util/get_category_query';
 import { recallFromConnectors } from './recall_from_connectors';
@@ -355,6 +360,9 @@ export class KnowledgeBaseService {
             namespace,
           }),
           ...getCategoryQuery({ categories }),
+
+          // exclude user instructions
+          { bool: { must_not: { term: { type: KnowledgeBaseType.UserInstruction } } } },
         ],
       },
     };
@@ -425,6 +433,13 @@ export class KnowledgeBaseService {
       }),
     ]);
 
+    this.dependencies.logger.debug(
+      `documentsFromKb: ${JSON.stringify(documentsFromKb.slice(0, 5), null, 2)}`
+    );
+    this.dependencies.logger.debug(
+      `documentsFromConnectors: ${JSON.stringify(documentsFromConnectors.slice(0, 5), null, 2)}`
+    );
+
     const sortedEntries = orderBy(
       documentsFromKb.concat(documentsFromConnectors),
       'score',
@@ -458,34 +473,30 @@ export class KnowledgeBaseService {
   getUserInstructions = async (
     namespace: string,
     user?: { name: string }
-  ): Promise<UserInstruction[]> => {
+  ): Promise<Array<Instruction & { public?: boolean }>> => {
     try {
       const response = await this.dependencies.esClient.asInternalUser.search<KnowledgeBaseEntry>({
         index: resourceNames.aliases.kb,
         query: {
           bool: {
-            must: [
+            filter: [
               {
                 term: {
-                  'labels.category.keyword': {
-                    value: 'instruction',
-                  },
+                  type: KnowledgeBaseType.UserInstruction,
                 },
               },
+              ...getAccessQuery({ user, namespace }),
             ],
-            filter: getAccessQuery({
-              user,
-              namespace,
-            }),
           },
         },
         size: 500,
-        _source: ['doc_id', 'text'],
+        _source: ['doc_id', 'text', 'public'],
       });
 
       return response.hits.hits.map((hit) => ({
         doc_id: hit._source?.doc_id ?? '',
         text: hit._source?.text ?? '',
+        public: hit._source?.public,
       }));
     } catch (error) {
       this.dependencies.logger.error('Failed to load instructions from knowledge base');
@@ -506,17 +517,18 @@ export class KnowledgeBaseService {
     try {
       const response = await this.dependencies.esClient.asInternalUser.search<KnowledgeBaseEntry>({
         index: resourceNames.aliases.kb,
-        ...(query
-          ? {
-              query: {
-                wildcard: {
-                  doc_id: {
-                    value: `${query}*`,
-                  },
-                },
+        query: {
+          bool: {
+            filter: [
+              // filter title by query
+              ...(query ? [{ wildcard: { doc_id: { value: `${query}*` } } }] : []),
+              {
+                // exclude user instructions
+                bool: { must_not: { term: { type: KnowledgeBaseType.UserInstruction } } },
               },
-            }
-          : {}),
+            ],
+          },
+        },
         sort: [
           {
             [String(sortBy)]: {
@@ -536,6 +548,7 @@ export class KnowledgeBaseService {
             '@timestamp',
             'role',
             'user.name',
+            'type',
           ],
         },
       });
@@ -556,6 +569,35 @@ export class KnowledgeBaseService {
     }
   };
 
+  getExistingUserInstructionId = async ({
+    isPublic,
+    user,
+    namespace,
+  }: {
+    isPublic: boolean;
+    user?: { name: string; id?: string };
+    namespace?: string;
+  }) => {
+    const res = await this.dependencies.esClient.asInternalUser.search<
+      Pick<KnowledgeBaseEntry, 'doc_id'>
+    >({
+      index: resourceNames.aliases.kb,
+      query: {
+        bool: {
+          filter: [
+            { term: { type: KnowledgeBaseType.UserInstruction } },
+            { term: { public: isPublic } },
+            ...getAccessQuery({ user, namespace }),
+          ],
+        },
+      },
+      size: 1,
+      _source: ['doc_id'],
+    });
+
+    return res.hits.hits[0]?._source?.doc_id;
+  };
+
   addEntry = async ({
     entry: { id, ...document },
     user,
@@ -565,6 +607,20 @@ export class KnowledgeBaseService {
     user?: { name: string; id?: string };
     namespace?: string;
   }): Promise<void> => {
+    // for now we want to limit the number of user instructions to 1 per user
+    if (document.type === KnowledgeBaseType.UserInstruction) {
+      const existingId = await this.getExistingUserInstructionId({
+        isPublic: document.public,
+        user,
+        namespace,
+      });
+
+      if (existingId) {
+        id = existingId;
+        document.doc_id = existingId;
+      }
+    }
+
     try {
       await this.dependencies.esClient.asInternalUser.index({
         index: resourceNames.aliases.kb,
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/types.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/types.ts
index 6e6256c3b8b90..cd8e25843ca59 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/types.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/types.ts
@@ -16,7 +16,7 @@ import type {
 import type {
   Message,
   ObservabilityAIAssistantScreenContextRequest,
-  UserInstructionOrPlainText,
+  InstructionOrPlainText,
 } from '../../common/types';
 import type { ObservabilityAIAssistantRouteHandlerResources } from '../routes/types';
 import { ChatFunctionClient } from './chat_function_client';
@@ -63,17 +63,15 @@ export interface FunctionHandler {
   respond: RespondFunction<any, FunctionResponse>;
 }
 
-export type RegisteredInstruction = UserInstructionOrPlainText | RegisterInstructionCallback;
+export type InstructionOrCallback = InstructionOrPlainText | RegisterInstructionCallback;
 
 type RegisterInstructionCallback = ({
   availableFunctionNames,
 }: {
   availableFunctionNames: string[];
-}) => UserInstructionOrPlainText | UserInstructionOrPlainText[] | undefined;
+}) => InstructionOrPlainText | InstructionOrPlainText[] | undefined;
 
-export type RegisterInstruction = (
-  ...instructions: Array<UserInstructionOrPlainText | RegisterInstructionCallback>
-) => void;
+export type RegisterInstruction = (...instructions: InstructionOrCallback[]) => void;
 
 export type RegisterFunction = <
   TParameters extends CompatibleJSONSchema = any,
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/util/get_system_message_from_instructions.test.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/util/get_system_message_from_instructions.test.ts
index 93594fc520998..8e4075bed7b9d 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/util/get_system_message_from_instructions.test.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/util/get_system_message_from_instructions.test.ts
@@ -13,9 +13,9 @@ describe('getSystemMessageFromInstructions', () => {
   it('handles plain instructions', () => {
     expect(
       getSystemMessageFromInstructions({
-        registeredInstructions: ['first', 'second'],
+        applicationInstructions: ['first', 'second'],
         userInstructions: [],
-        requestInstructions: [],
+        adHocInstructions: [],
         availableFunctionNames: [],
       })
     ).toEqual(`first\n\nsecond`);
@@ -24,36 +24,42 @@ describe('getSystemMessageFromInstructions', () => {
   it('handles callbacks', () => {
     expect(
       getSystemMessageFromInstructions({
-        registeredInstructions: [
+        applicationInstructions: [
           'first',
           ({ availableFunctionNames }) => {
             return availableFunctionNames[0];
           },
         ],
         userInstructions: [],
-        requestInstructions: [],
+        adHocInstructions: [],
         availableFunctionNames: ['myFunction'],
       })
     ).toEqual(`first\n\nmyFunction`);
   });
 
-  it('overrides kb instructions with request instructions', () => {
+  it('overrides kb instructions with adhoc instructions', () => {
     expect(
       getSystemMessageFromInstructions({
-        registeredInstructions: ['first'],
-        userInstructions: [{ doc_id: 'second', text: 'second_kb' }],
-        requestInstructions: [{ doc_id: 'second', text: 'second_request' }],
+        applicationInstructions: ['first'],
+        userInstructions: [{ doc_id: 'second', text: 'second from kb' }],
+        adHocInstructions: [
+          {
+            doc_id: 'second',
+            text: 'second from adhoc instruction',
+            instruction_type: 'user_instruction',
+          },
+        ],
         availableFunctionNames: [],
       })
-    ).toEqual(`first\n\n${USER_INSTRUCTIONS_HEADER}\n\nsecond_request`);
+    ).toEqual(`first\n\n${USER_INSTRUCTIONS_HEADER}\n\nsecond from adhoc instruction`);
   });
 
   it('includes kb instructions if there is no request instruction', () => {
     expect(
       getSystemMessageFromInstructions({
-        registeredInstructions: ['first'],
+        applicationInstructions: ['first'],
         userInstructions: [{ doc_id: 'second', text: 'second_kb' }],
-        requestInstructions: [],
+        adHocInstructions: [],
         availableFunctionNames: [],
       })
     ).toEqual(`first\n\n${USER_INSTRUCTIONS_HEADER}\n\nsecond_kb`);
@@ -62,14 +68,14 @@ describe('getSystemMessageFromInstructions', () => {
   it('handles undefined values', () => {
     expect(
       getSystemMessageFromInstructions({
-        registeredInstructions: [
+        applicationInstructions: [
           'first',
           ({ availableFunctionNames }) => {
             return undefined;
           },
         ],
         userInstructions: [],
-        requestInstructions: [],
+        adHocInstructions: [],
         availableFunctionNames: [],
       })
     ).toEqual(`first`);
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/util/get_system_message_from_instructions.ts b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/util/get_system_message_from_instructions.ts
index 759ff07125b95..b2797577883ba 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/util/get_system_message_from_instructions.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant/server/service/util/get_system_message_from_instructions.ts
@@ -5,11 +5,11 @@
  * 2.0.
  */
 
-import { compact, partition } from 'lodash';
+import { compact, partition, uniqBy } from 'lodash';
 import { v4 } from 'uuid';
-import { UserInstruction, UserInstructionOrPlainText } from '../../../common/types';
+import { AdHocInstruction, Instruction } from '../../../common/types';
 import { withTokenBudget } from '../../../common/utils/with_token_budget';
-import { RegisteredInstruction } from '../types';
+import { InstructionOrCallback } from '../types';
 
 export const USER_INSTRUCTIONS_HEADER = `## User instructions
           
@@ -19,18 +19,23 @@ as long as they don't conflict with anything you've been told so far:
 `;
 
 export function getSystemMessageFromInstructions({
-  registeredInstructions,
-  userInstructions,
-  requestInstructions,
+  // application instructions registered by the functions. These will be displayed first
+  applicationInstructions,
+
+  // instructions provided by the user. These will be displayed after the application instructions and only if they fit within the token budget
+  userInstructions: kbUserInstructions,
+
+  // ad-hoc instruction. Can be either user or application instruction
+  adHocInstructions,
   availableFunctionNames,
 }: {
-  registeredInstructions: RegisteredInstruction[];
-  userInstructions: UserInstruction[];
-  requestInstructions: UserInstructionOrPlainText[];
+  applicationInstructions: InstructionOrCallback[];
+  userInstructions: Instruction[];
+  adHocInstructions: AdHocInstruction[];
   availableFunctionNames: string[];
 }): string {
-  const allRegisteredInstructions = compact(
-    registeredInstructions.flatMap((instruction) => {
+  const allApplicationInstructions = compact(
+    applicationInstructions.flatMap((instruction) => {
       if (typeof instruction === 'function') {
         return instruction({ availableFunctionNames });
       }
@@ -38,31 +43,30 @@ export function getSystemMessageFromInstructions({
     })
   );
 
-  const requestInstructionsWithId = requestInstructions.map((instruction) =>
-    typeof instruction === 'string'
-      ? { doc_id: v4(), text: instruction, system: false }
-      : instruction
-  );
+  const adHocInstructionsWithId = adHocInstructions.map((adHocInstruction) => ({
+    ...adHocInstruction,
+    doc_id: adHocInstruction.doc_id ?? v4(),
+  }));
 
-  const [requestSystemInstructions, requestUserInstructionsWithId] = partition(
-    requestInstructionsWithId,
-    (instruction) => instruction.system === true
+  // split ad hoc instructions into user instructions and application instructions
+  const [adHocUserInstructions, adHocApplicationInstructions] = partition(
+    adHocInstructionsWithId,
+    (instruction) => instruction.instruction_type === 'user_instruction'
   );
 
-  const requestOverrideIds = requestUserInstructionsWithId.map((instruction) => instruction.doc_id);
-
-  // all request instructions, and those from the KB that are not defined as a request instruction
-  const allUserInstructions = requestInstructionsWithId.concat(
-    userInstructions.filter((instruction) => !requestOverrideIds.includes(instruction.doc_id))
+  // all adhoc instructions and KB instructions.
+  // adhoc instructions will be prioritized over Knowledge Base instructions if the doc_id is the same
+  const allUserInstructions = withTokenBudget(
+    uniqBy([...adHocUserInstructions, ...kbUserInstructions], (i) => i.doc_id),
+    1000
   );
 
-  const instructionsWithinBudget = withTokenBudget(allUserInstructions, 1000);
-
   return [
-    ...allRegisteredInstructions.concat(requestSystemInstructions),
-    ...(instructionsWithinBudget.length
-      ? [USER_INSTRUCTIONS_HEADER, ...instructionsWithinBudget]
-      : []),
+    // application instructions
+    ...allApplicationInstructions.concat(adHocApplicationInstructions),
+
+    // user instructions
+    ...(allUserInstructions.length ? [USER_INSTRUCTIONS_HEADER, ...allUserInstructions] : []),
   ]
     .map((instruction) => {
       return typeof instruction === 'string' ? instruction : instruction.text;
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant_app/kibana.jsonc b/x-pack/plugins/observability_solution/observability_ai_assistant_app/kibana.jsonc
index 7408f5e5dd1c9..6e2ba07fb699c 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant_app/kibana.jsonc
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant_app/kibana.jsonc
@@ -20,11 +20,10 @@
       "uiActions",
       "triggersActionsUi",
       "share",
-      "security",
       "licensing",
       "ml",
       "alerting",
-      "features",
+      "features"
     ],
     "requiredBundles": ["kibanaReact", "esqlDataGrid"],
     "optionalPlugins": ["cloud"],
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant_app/public/hooks/use_current_user.ts b/x-pack/plugins/observability_solution/observability_ai_assistant_app/public/hooks/use_current_user.ts
index 1ca539eb88370..82c13eb876117 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant_app/public/hooks/use_current_user.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant_app/public/hooks/use_current_user.ts
@@ -11,11 +11,7 @@ import { useKibana } from './use_kibana';
 
 export function useCurrentUser() {
   const {
-    services: {
-      plugins: {
-        start: { security },
-      },
-    },
+    services: { security },
   } = useKibana();
 
   const [user, setUser] = useState<AuthenticatedUser>();
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant_app/public/types.ts b/x-pack/plugins/observability_solution/observability_ai_assistant_app/public/types.ts
index d6235da273839..398ef5f3afe4c 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant_app/public/types.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant_app/public/types.ts
@@ -16,7 +16,6 @@ import type {
   ObservabilityAIAssistantPublicStart,
 } from '@kbn/observability-ai-assistant-plugin/public';
 import type { SharePluginSetup, SharePluginStart } from '@kbn/share-plugin/public';
-import type { SecurityPluginStart, SecurityPluginSetup } from '@kbn/security-plugin/public';
 import type { LicensingPluginSetup, LicensingPluginStart } from '@kbn/licensing-plugin/public';
 import type {
   ObservabilitySharedPluginSetup,
@@ -41,7 +40,6 @@ export interface ObservabilityAIAssistantAppPublicSetup {}
 export interface ObservabilityAIAssistantAppPluginStartDependencies {
   licensing: LicensingPluginStart;
   share: SharePluginStart;
-  security: SecurityPluginStart;
   lens: LensPublicStart;
   dataViews: DataViewsPublicPluginStart;
   uiActions: UiActionsStart;
@@ -56,7 +54,6 @@ export interface ObservabilityAIAssistantAppPluginStartDependencies {
 export interface ObservabilityAIAssistantAppPluginSetupDependencies {
   licensing: LicensingPluginSetup;
   share: SharePluginSetup;
-  security: SecurityPluginSetup;
   lens: LensPublicSetup;
   dataViews: DataViewsPublicPluginSetup;
   uiActions: UiActionsSetup;
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant_app/server/rule_connector/index.ts b/x-pack/plugins/observability_solution/observability_ai_assistant_app/server/rule_connector/index.ts
index aac5637e7d5bb..34b9dd36ea77f 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant_app/server/rule_connector/index.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant_app/server/rule_connector/index.ts
@@ -36,6 +36,7 @@ import { concatenateChatCompletionChunks } from '@kbn/observability-ai-assistant
 import { CompatibleJSONSchema } from '@kbn/observability-ai-assistant-plugin/common/functions/types';
 import { AlertDetailsContextualInsightsService } from '@kbn/observability-plugin/server/services';
 import { getSystemMessageFromInstructions } from '@kbn/observability-ai-assistant-plugin/server/service/util/get_system_message_from_instructions';
+import { AdHocInstruction } from '@kbn/observability-ai-assistant-plugin/common/types';
 import { convertSchemaToOpenApi } from './convert_schema_to_open_api';
 import { OBSERVABILITY_AI_ASSISTANT_CONNECTOR_ID } from '../../common/rule_connector';
 
@@ -177,12 +178,15 @@ async function executor(
     });
   });
 
-  const backgroundInstruction = dedent(
-    `You are called as a background process because alerts have changed state.
-    As a background process you are not interacting with a user. Because of that DO NOT ask for user
-    input if tasked to execute actions. You can generate multiple responses in a row.
-    If available, include the link of the conversation at the end of your answer.`
-  );
+  const backgroundInstruction: AdHocInstruction = {
+    instruction_type: 'application_instruction',
+    text: dedent(
+      `You are called as a background process because alerts have changed state.
+As a background process you are not interacting with a user. Because of that DO NOT ask for user
+input if tasked to execute actions. You can generate multiple responses in a row.
+If available, include the link of the conversation at the end of your answer.`
+    ),
+  };
 
   const alertsContext = await getAlertsContext(
     execOptions.params.rule,
@@ -223,9 +227,9 @@ async function executor(
             role: MessageRole.System,
             content: getSystemMessageFromInstructions({
               availableFunctionNames: functionClient.getFunctions().map((fn) => fn.definition.name),
-              registeredInstructions: functionClient.getInstructions(),
+              applicationInstructions: functionClient.getInstructions(),
               userInstructions: [],
-              requestInstructions: [],
+              adHocInstructions: [],
             }),
           },
         },
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/constants.ts b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/constants.ts
index d48005c41cd62..a680da5ed3f93 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/constants.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/constants.ts
@@ -8,6 +8,7 @@
 export const REACT_QUERY_KEYS = {
   GET_GENAI_CONNECTORS: 'get_genai_connectors',
   GET_KB_ENTRIES: 'get_kb_entries',
+  GET_KB_USER_INSTRUCTIONS: 'get_kb_user_instructions',
   CREATE_KB_ENTRIES: 'create_kb_entry',
   IMPORT_KB_ENTRIES: 'import_kb_entry',
 };
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_create_knowledge_base_entry.ts b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_create_knowledge_base_entry.ts
index 57bf36c507a7a..459de7be2d528 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_create_knowledge_base_entry.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_create_knowledge_base_entry.ts
@@ -22,7 +22,7 @@ export function useCreateKnowledgeBaseEntry() {
   } = useKibana().services;
 
   const queryClient = useQueryClient();
-  const observabilityAIAssistantApi = observabilityAIAssistant?.service.callApi;
+  const observabilityAIAssistantApi = observabilityAIAssistant.service.callApi;
 
   return useMutation<
     void,
@@ -36,11 +36,7 @@ export function useCreateKnowledgeBaseEntry() {
   >(
     [REACT_QUERY_KEYS.CREATE_KB_ENTRIES],
     ({ entry }) => {
-      if (!observabilityAIAssistantApi) {
-        return Promise.reject('Error with observabilityAIAssistantApi: API not found.');
-      }
-
-      return observabilityAIAssistantApi?.(
+      return observabilityAIAssistantApi(
         'POST /internal/observability_ai_assistant/kb/entries/save',
         {
           signal: null,
@@ -59,8 +55,7 @@ export function useCreateKnowledgeBaseEntry() {
           i18n.translate(
             'xpack.observabilityAiAssistantManagement.kb.addManualEntry.successNotification',
             {
-              defaultMessage: 'Successfully created {name}',
-              values: { name: entry.id },
+              defaultMessage: 'Entry saved',
             }
           )
         );
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_create_knowledge_base_user_instruction.ts b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_create_knowledge_base_user_instruction.ts
new file mode 100644
index 0000000000000..b51e45a3bdd6b
--- /dev/null
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_create_knowledge_base_user_instruction.ts
@@ -0,0 +1,72 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import { IHttpFetchError, ResponseErrorBody } from '@kbn/core/public';
+import { i18n } from '@kbn/i18n';
+import { useMutation, useQueryClient } from '@tanstack/react-query';
+import { type Instruction } from '@kbn/observability-ai-assistant-plugin/common/types';
+import { REACT_QUERY_KEYS } from '../constants';
+import { useKibana } from './use_kibana';
+
+type ServerError = IHttpFetchError<ResponseErrorBody>;
+
+export function useCreateKnowledgeBaseUserInstruction() {
+  const {
+    observabilityAIAssistant,
+    notifications: { toasts },
+  } = useKibana().services;
+
+  const queryClient = useQueryClient();
+  const observabilityAIAssistantApi = observabilityAIAssistant.service.callApi;
+
+  return useMutation<void, ServerError, { entry: Instruction & { public: boolean } }>(
+    [REACT_QUERY_KEYS.CREATE_KB_ENTRIES],
+    ({ entry }) => {
+      return observabilityAIAssistantApi(
+        'PUT /internal/observability_ai_assistant/kb/user_instructions',
+        {
+          signal: null,
+          params: {
+            body: {
+              id: entry.doc_id,
+              text: entry.text,
+              public: entry.public,
+            },
+          },
+        }
+      );
+    },
+    {
+      onSuccess: (_data, { entry }) => {
+        toasts.addSuccess(
+          i18n.translate(
+            'xpack.observabilityAiAssistantManagement.kb.addUserInstruction.successNotification',
+            {
+              defaultMessage: 'User instruction saved',
+            }
+          )
+        );
+
+        queryClient.invalidateQueries({
+          queryKey: [REACT_QUERY_KEYS.GET_KB_USER_INSTRUCTIONS],
+          refetchType: 'all',
+        });
+      },
+      onError: (error, { entry }) => {
+        toasts.addError(new Error(error.body?.message ?? error.message), {
+          title: i18n.translate(
+            'xpack.observabilityAiAssistantManagement.kb.addUserInstruction.errorNotification',
+            {
+              defaultMessage: 'Something went wrong while creating {name}',
+              values: { name: entry.doc_id },
+            }
+          ),
+        });
+      },
+    }
+  );
+}
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_delete_knowledge_base_entry.ts b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_delete_knowledge_base_entry.ts
index 3013a99bb3ed1..5d4f2b9e6eee4 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_delete_knowledge_base_entry.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_delete_knowledge_base_entry.ts
@@ -20,16 +20,12 @@ export function useDeleteKnowledgeBaseEntry() {
   } = useKibana().services;
 
   const queryClient = useQueryClient();
-  const observabilityAIAssistantApi = observabilityAIAssistant?.service.callApi;
+  const observabilityAIAssistantApi = observabilityAIAssistant.service.callApi;
 
   return useMutation<unknown, ServerError, { id: string }>(
     [REACT_QUERY_KEYS.CREATE_KB_ENTRIES],
     ({ id: entryId }) => {
-      if (!observabilityAIAssistantApi) {
-        return Promise.reject('Error with observabilityAIAssistantApi: API not found.');
-      }
-
-      return observabilityAIAssistantApi?.(
+      return observabilityAIAssistantApi(
         'DELETE /internal/observability_ai_assistant/kb/entries/{entryId}',
         {
           signal: null,
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_get_knowledge_base_entries.ts b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_get_knowledge_base_entries.ts
index 167e2cfe71a56..c1a119d6a0f49 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_get_knowledge_base_entries.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_get_knowledge_base_entries.ts
@@ -20,13 +20,13 @@ export function useGetKnowledgeBaseEntries({
 }) {
   const { observabilityAIAssistant } = useKibana().services;
 
-  const observabilityAIAssistantApi = observabilityAIAssistant?.service.callApi;
+  const observabilityAIAssistantApi = observabilityAIAssistant.service.callApi;
 
   const { isLoading, isError, isSuccess, isRefetching, data, refetch } = useQuery({
     queryKey: [REACT_QUERY_KEYS.GET_KB_ENTRIES, query, sortBy, sortDirection],
     queryFn: async ({ signal }) => {
-      if (!observabilityAIAssistantApi || !signal) {
-        return Promise.reject('Error with observabilityAIAssistantApi: API not found.');
+      if (!signal) {
+        throw new Error('Abort signal missing');
       }
 
       return observabilityAIAssistantApi(`GET /internal/observability_ai_assistant/kb/entries`, {
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_get_user_instructions.ts b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_get_user_instructions.ts
new file mode 100644
index 0000000000000..ea59062c55c7e
--- /dev/null
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_get_user_instructions.ts
@@ -0,0 +1,38 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import { useQuery } from '@tanstack/react-query';
+import { REACT_QUERY_KEYS } from '../constants';
+import { useKibana } from './use_kibana';
+
+export function useGetUserInstructions() {
+  const { observabilityAIAssistant } = useKibana().services;
+  const observabilityAIAssistantApi = observabilityAIAssistant.service.callApi;
+
+  const { isLoading, isError, isSuccess, isRefetching, data, refetch } = useQuery({
+    queryKey: [REACT_QUERY_KEYS.GET_KB_USER_INSTRUCTIONS],
+    queryFn: async ({ signal }) => {
+      if (!signal) {
+        throw new Error('Abort signal missing');
+      }
+
+      return observabilityAIAssistantApi(
+        `GET /internal/observability_ai_assistant/kb/user_instructions`,
+        { signal }
+      );
+    },
+  });
+
+  return {
+    userInstructions: data?.userInstructions,
+    refetch,
+    isLoading,
+    isRefetching,
+    isSuccess,
+    isError,
+  };
+}
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_import_knowledge_base_entries.ts b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_import_knowledge_base_entries.ts
index d415a5e6977c4..9ff0748793bc8 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_import_knowledge_base_entries.ts
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/hooks/use_import_knowledge_base_entries.ts
@@ -20,7 +20,7 @@ export function useImportKnowledgeBaseEntries() {
     notifications: { toasts },
   } = useKibana().services;
   const queryClient = useQueryClient();
-  const observabilityAIAssistantApi = observabilityAIAssistant?.service.callApi;
+  const observabilityAIAssistantApi = observabilityAIAssistant.service.callApi;
 
   return useMutation<
     void,
@@ -36,11 +36,7 @@ export function useImportKnowledgeBaseEntries() {
   >(
     [REACT_QUERY_KEYS.IMPORT_KB_ENTRIES],
     ({ entries }) => {
-      if (!observabilityAIAssistantApi) {
-        return Promise.reject('Error with observabilityAIAssistantApi: API not found.');
-      }
-
-      return observabilityAIAssistantApi?.(
+      return observabilityAIAssistantApi(
         'POST /internal/observability_ai_assistant/kb/entries/import',
         {
           signal: null,
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/routes/components/knowledge_base_edit_user_instruction_flyout.tsx b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/routes/components/knowledge_base_edit_user_instruction_flyout.tsx
new file mode 100644
index 0000000000000..8b12f842bf128
--- /dev/null
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/routes/components/knowledge_base_edit_user_instruction_flyout.tsx
@@ -0,0 +1,133 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import React, { useEffect, useState } from 'react';
+import { i18n } from '@kbn/i18n';
+import {
+  EuiButton,
+  EuiButtonEmpty,
+  EuiFlexGroup,
+  EuiFlexItem,
+  EuiFlyout,
+  EuiFlyoutBody,
+  EuiFlyoutFooter,
+  EuiFlyoutHeader,
+  EuiFormRow,
+  EuiMarkdownEditor,
+  EuiSpacer,
+  EuiText,
+  EuiTitle,
+} from '@elastic/eui';
+import { v4 as uuidv4 } from 'uuid';
+import { useGetUserInstructions } from '../../hooks/use_get_user_instructions';
+import { useCreateKnowledgeBaseUserInstruction } from '../../hooks/use_create_knowledge_base_user_instruction';
+
+export function KnowledgeBaseEditUserInstructionFlyout({ onClose }: { onClose: () => void }) {
+  const { userInstructions, isLoading: isFetching } = useGetUserInstructions();
+  const { mutateAsync: createEntry, isLoading: isSaving } = useCreateKnowledgeBaseUserInstruction();
+  const [newEntryText, setNewEntryText] = useState('');
+  const [newEntryDocId, setNewEntryDocId] = useState<string>();
+  const isSubmitDisabled = newEntryText.trim() === '';
+
+  useEffect(() => {
+    const userInstruction = userInstructions?.find((entry) => !entry.public);
+    setNewEntryDocId(userInstruction?.doc_id);
+    setNewEntryText(userInstruction?.text ?? '');
+  }, [userInstructions]);
+
+  const handleSubmit = async () => {
+    await createEntry({
+      entry: {
+        doc_id: newEntryDocId ?? uuidv4(),
+        text: newEntryText,
+        public: false, // limit user instructions to private (for now)
+      },
+    });
+
+    onClose();
+  };
+
+  return (
+    <EuiFlyout onClose={onClose}>
+      <EuiFlyoutHeader hasBorder data-test-subj="knowledgeBaseManualEntryFlyout">
+        <EuiTitle>
+          <h2>
+            {i18n.translate(
+              'xpack.observabilityAiAssistantManagement.knowledgeBaseEditSystemPrompt.h2.editEntryLabel',
+              { defaultMessage: 'AI User Profile' }
+            )}
+          </h2>
+        </EuiTitle>
+      </EuiFlyoutHeader>
+
+      <EuiFlyoutBody>
+        <EuiText>
+          {i18n.translate(
+            'xpack.observabilityAiAssistantManagement.knowledgeBaseEditSystemPromptFlyout.personalPromptTextLabel',
+            {
+              defaultMessage:
+                'The AI User Profile will be appended to the system prompt. It is space-aware and will only be used for your prompts - not shared with other users.',
+            }
+          )}
+        </EuiText>
+
+        <EuiSpacer size="s" />
+
+        <EuiFormRow fullWidth>
+          <EuiMarkdownEditor
+            editorId="knowledgeBaseEditManualEntryFlyoutMarkdownEditor"
+            aria-label={i18n.translate(
+              'xpack.observabilityAiAssistantManagement.knowledgeBaseNewManualEntryFlyout.euiMarkdownEditor.observabilityAiAssistantKnowledgeBaseViewMarkdownEditorLabel',
+              { defaultMessage: 'observabilityAiAssistantKnowledgeBaseViewMarkdownEditor' }
+            )}
+            height={300}
+            initialViewMode="editing"
+            readOnly={isFetching}
+            placeholder={i18n.translate(
+              'xpack.observabilityAiAssistantManagement.knowledgeBaseEditManualEntryFlyout.euiMarkdownEditor.enterContentsLabel',
+              { defaultMessage: 'Enter contents' }
+            )}
+            value={newEntryText}
+            onChange={(text) => setNewEntryText(text)}
+          />
+        </EuiFormRow>
+        <EuiSpacer size="m" />
+      </EuiFlyoutBody>
+
+      <EuiFlyoutFooter>
+        <EuiFlexGroup justifyContent="spaceBetween">
+          <EuiFlexItem grow={false}>
+            <EuiButtonEmpty
+              data-test-subj="knowledgeBaseEditManualEntryFlyoutCancelButton"
+              disabled={isSaving}
+              onClick={onClose}
+            >
+              {i18n.translate(
+                'xpack.observabilityAiAssistantManagement.knowledgeBaseNewManualEntryFlyout.cancelButtonEmptyLabel',
+                { defaultMessage: 'Cancel' }
+              )}
+            </EuiButtonEmpty>
+          </EuiFlexItem>
+          <EuiFlexItem grow={false}>
+            <EuiButton
+              data-test-subj="knowledgeBaseEditManualEntryFlyoutSaveButton"
+              fill
+              isLoading={isSaving}
+              onClick={handleSubmit}
+              isDisabled={isSubmitDisabled}
+            >
+              {i18n.translate(
+                'xpack.observabilityAiAssistantManagement.knowledgeBaseNewManualEntryFlyout.saveButtonLabel',
+                { defaultMessage: 'Save' }
+              )}
+            </EuiButton>
+          </EuiFlexItem>
+        </EuiFlexGroup>
+      </EuiFlyoutFooter>
+    </EuiFlyout>
+  );
+}
diff --git a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/routes/components/knowledge_base_tab.tsx b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/routes/components/knowledge_base_tab.tsx
index 4257833dde714..de27f26f2561c 100644
--- a/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/routes/components/knowledge_base_tab.tsx
+++ b/x-pack/plugins/observability_solution/observability_ai_assistant_management/public/routes/components/knowledge_base_tab.tsx
@@ -24,13 +24,14 @@ import {
   EuiScreenReaderOnly,
 } from '@elastic/eui';
 import moment from 'moment';
-import type { KnowledgeBaseEntry } from '@kbn/observability-ai-assistant-plugin/common/types';
+import { KnowledgeBaseEntry } from '@kbn/observability-ai-assistant-plugin/public';
 import { useGetKnowledgeBaseEntries } from '../../hooks/use_get_knowledge_base_entries';
 import { categorizeEntries, KnowledgeBaseEntryCategory } from '../../helpers/categorize_entries';
 import { KnowledgeBaseEditManualEntryFlyout } from './knowledge_base_edit_manual_entry_flyout';
 import { KnowledgeBaseCategoryFlyout } from './knowledge_base_category_flyout';
 import { KnowledgeBaseBulkImportFlyout } from './knowledge_base_bulk_import_flyout';
 import { useKibana } from '../../hooks/use_kibana';
+import { KnowledgeBaseEditUserInstructionFlyout } from './knowledge_base_edit_user_instruction_flyout';
 
 export function KnowledgeBaseTab() {
   const { uiSettings } = useKibana().services;
@@ -175,11 +176,12 @@ export function KnowledgeBaseTab() {
     KnowledgeBaseEntryCategory | undefined
   >();
 
-  const [flyoutOpenType, setFlyoutOpenType] = useState<
-    'singleEntry' | 'bulkImport' | 'category' | undefined
+  const [newEntryFlyoutType, setNewEntryFlyoutType] = useState<
+    'singleEntry' | 'bulkImport' | undefined
   >();
 
-  const [newEntryPopoverOpen, setNewEntryPopoverOpen] = useState(false);
+  const [isNewEntryPopoverOpen, setIsNewEntryPopoverOpen] = useState(false);
+  const [isEditUserInstructionFlyoutOpen, setIsEditUserInstructionFlyoutOpen] = useState(false);
   const [query, setQuery] = useState('');
   const [sortBy, setSortBy] = useState<'doc_id' | '@timestamp'>('doc_id');
   const [sortDirection, setSortDirection] = useState<'asc' | 'desc'>('asc');
@@ -206,10 +208,6 @@ export function KnowledgeBaseTab() {
     }
   };
 
-  const handleClickNewEntry = () => {
-    setNewEntryPopoverOpen(true);
-  };
-
   const handleChangeQuery = (e: React.ChangeEvent<HTMLInputElement> | undefined) => {
     setQuery(e?.currentTarget.value || '');
   };
@@ -236,6 +234,7 @@ export function KnowledgeBaseTab() {
                 )}
               />
             </EuiFlexItem>
+
             <EuiFlexItem grow={false}>
               <EuiButton
                 data-test-subj="knowledgeBaseTabReloadButton"
@@ -249,17 +248,30 @@ export function KnowledgeBaseTab() {
                 )}
               </EuiButton>
             </EuiFlexItem>
+            <EuiFlexItem grow={false}>
+              <EuiButton
+                data-test-subj="observabilityAiAssistantManagementKnowledgeBaseTabEditInstructionsButton"
+                color="text"
+                onClick={() => setIsEditUserInstructionFlyoutOpen(true)}
+              >
+                {i18n.translate(
+                  'xpack.observabilityAiAssistantManagement.knowledgeBaseTab.editInstructionsButtonLabel',
+                  { defaultMessage: 'Edit AI User Profile' }
+                )}
+              </EuiButton>
+            </EuiFlexItem>
+
             <EuiFlexItem grow={false}>
               <EuiPopover
-                isOpen={newEntryPopoverOpen}
-                closePopover={() => setNewEntryPopoverOpen(false)}
+                isOpen={isNewEntryPopoverOpen}
+                closePopover={() => setIsNewEntryPopoverOpen(false)}
                 button={
                   <EuiButton
                     fill
                     data-test-subj="knowledgeBaseNewEntryButton"
                     iconSide="right"
                     iconType="arrowDown"
-                    onClick={handleClickNewEntry}
+                    onClick={() => setIsNewEntryPopoverOpen((prevValue) => !prevValue)}
                   >
                     {i18n.translate(
                       'xpack.observabilityAiAssistantManagement.knowledgeBaseTab.newEntryButtonLabel',
@@ -278,8 +290,8 @@ export function KnowledgeBaseTab() {
                       icon="document"
                       data-test-subj="knowledgeBaseSingleEntryContextMenuItem"
                       onClick={() => {
-                        setNewEntryPopoverOpen(false);
-                        setFlyoutOpenType('singleEntry');
+                        setIsNewEntryPopoverOpen(false);
+                        setNewEntryFlyoutType('singleEntry');
                       }}
                       size="s"
                     >
@@ -293,8 +305,8 @@ export function KnowledgeBaseTab() {
                       icon="documents"
                       data-test-subj="knowledgeBaseBulkImportContextMenuItem"
                       onClick={() => {
-                        setNewEntryPopoverOpen(false);
-                        setFlyoutOpenType('bulkImport');
+                        setIsNewEntryPopoverOpen(false);
+                        setNewEntryFlyoutType('bulkImport');
                       }}
                     >
                       {i18n.translate(
@@ -329,12 +341,18 @@ export function KnowledgeBaseTab() {
         </EuiFlexItem>
       </EuiFlexGroup>
 
-      {flyoutOpenType === 'singleEntry' ? (
-        <KnowledgeBaseEditManualEntryFlyout onClose={() => setFlyoutOpenType(undefined)} />
+      {isEditUserInstructionFlyoutOpen ? (
+        <KnowledgeBaseEditUserInstructionFlyout
+          onClose={() => setIsEditUserInstructionFlyoutOpen(false)}
+        />
+      ) : null}
+
+      {newEntryFlyoutType === 'singleEntry' ? (
+        <KnowledgeBaseEditManualEntryFlyout onClose={() => setNewEntryFlyoutType(undefined)} />
       ) : null}
 
-      {flyoutOpenType === 'bulkImport' ? (
-        <KnowledgeBaseBulkImportFlyout onClose={() => setFlyoutOpenType(undefined)} />
+      {newEntryFlyoutType === 'bulkImport' ? (
+        <KnowledgeBaseBulkImportFlyout onClose={() => setNewEntryFlyoutType(undefined)} />
       ) : null}
 
       {selectedCategory ? (
diff --git a/x-pack/plugins/translations/translations/fr-FR.json b/x-pack/plugins/translations/translations/fr-FR.json
index cc0f7067d89e0..43b621fff0144 100644
--- a/x-pack/plugins/translations/translations/fr-FR.json
+++ b/x-pack/plugins/translations/translations/fr-FR.json
@@ -11131,8 +11131,8 @@
     "xpack.apm.serviceIcons.service": "Service",
     "xpack.apm.serviceIcons.serviceDetails.cloud.architecture": "Architecture",
     "xpack.apm.serviceIcons.serviceDetails.cloud.availabilityZoneLabel": "{zones, plural, =0 {Zone de disponibilité} one {Zone de disponibilité} other {Zones de disponibilité}} ",
-    "xpack.apm.serviceIcons.serviceDetails.cloud.faasTriggerTypeLabel": "{triggerTypes, plural, =0 {Type de déclencheur} one {Type de déclencheur} other {Types de déclencheurs}} ",
     "xpack.apm.serviceIcons.serviceDetails.cloud.functionNameLabel": "{functionNames, plural, =0 {Nom de fonction} one {Nom de fonction} other {Noms de fonction}} ",
+    "xpack.apm.serviceIcons.serviceDetails.cloud.faasTriggerTypeLabel": "{triggerTypes, plural, =0 {Type de déclencheur} one {Type de déclencheur} other {Types de déclencheurs}} ",
     "xpack.apm.serviceIcons.serviceDetails.cloud.machineTypesLabel": "{machineTypes, plural, =0{Type de machine} one {Type de machine} other {Types de machines}} ",
     "xpack.apm.serviceIcons.serviceDetails.cloud.projectIdLabel": "ID de projet",
     "xpack.apm.serviceIcons.serviceDetails.cloud.providerLabel": "Fournisseur cloud",
@@ -27088,8 +27088,8 @@
     "xpack.maps.source.esSearch.descendingLabel": "décroissant",
     "xpack.maps.source.esSearch.extentFilterLabel": "Filtre dynamique pour les données de la zone de carte visible",
     "xpack.maps.source.esSearch.fieldNotFoundMsg": "Impossible de trouver \"{fieldName}\" dans le modèle d'indexation \"{indexPatternName}\".",
-    "xpack.maps.source.esSearch.geofieldLabel": "Champ géospatial",
     "xpack.maps.source.esSearch.geoFieldLabel": "Champ géospatial",
+    "xpack.maps.source.esSearch.geofieldLabel": "Champ géospatial",
     "xpack.maps.source.esSearch.geoFieldTypeLabel": "Type de champ géospatial",
     "xpack.maps.source.esSearch.indexOverOneLengthEditError": "Votre vue de données pointe vers plusieurs index. Un seul index est autorisé par vue de données.",
     "xpack.maps.source.esSearch.indexZeroLengthEditError": "Votre vue de données ne pointe vers aucun index.",
@@ -36554,8 +36554,8 @@
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.maxAlertsFieldLessThanWarning": "Kibana ne permet qu'un maximum de {maxNumber} {maxNumber, plural, =1 {alerte} other {alertes}} par exécution de règle.",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.nameFieldRequiredError": "Nom obligatoire.",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutrule.noteHelpText": "Ajouter un guide d'investigation sur les règles...",
-    "xpack.securitySolution.detectionEngine.createRule.stepAboutrule.setupHelpText": "Ajouter le guide de configuration de règle...",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.setupHelpText": "Fournissez des instructions sur les conditions préalables à la règle, telles que les intégrations requises, les étapes de configuration et tout ce qui est nécessaire au bon fonctionnement de la règle.",
+    "xpack.securitySolution.detectionEngine.createRule.stepAboutrule.setupHelpText": "Ajouter le guide de configuration de règle...",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.setupLabel": "Guide de configuration",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.tagFieldEmptyError": "Une balise ne doit pas être vide",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.threatIndicatorPathFieldEmptyError": "Le remplacement du préfixe d'indicateur ne peut pas être vide.",
@@ -42193,8 +42193,8 @@
     "xpack.slo.sloEmbeddable.config.sloSelector.placeholder": "Sélectionner un SLO",
     "xpack.slo.sloEmbeddable.displayName": "Aperçu du SLO",
     "xpack.slo.sloEmbeddable.overview.sloNotFoundText": "Le SLO a été supprimé. Vous pouvez supprimer sans risque le widget du tableau de bord.",
-    "xpack.slo.sloGridItem.targetFlexItemLabel": "Cible {target}",
     "xpack.slo.sLOGridItem.targetFlexItemLabel": "Cible {target}",
+    "xpack.slo.sloGridItem.targetFlexItemLabel": "Cible {target}",
     "xpack.slo.sloGroupConfiguration.customFiltersLabel": "Personnaliser le filtre",
     "xpack.slo.sloGroupConfiguration.customFiltersOptional": "Facultatif",
     "xpack.slo.sloGroupConfiguration.customFilterText": "Personnaliser le filtre",
@@ -43640,8 +43640,8 @@
     "xpack.stackConnectors.components.casesWebhookxpack.stackConnectors.components.casesWebhook.connectorTypeTitle": "Webhook - Données de gestion des cas",
     "xpack.stackConnectors.components.d3security.bodyCodeEditorAriaLabel": "Éditeur de code",
     "xpack.stackConnectors.components.d3security.bodyFieldLabel": "Corps",
-    "xpack.stackConnectors.components.d3security.connectorTypeTitle": "Données D3",
     "xpack.stackConnectors.components.d3Security.connectorTypeTitle": "D3 Security",
+    "xpack.stackConnectors.components.d3security.connectorTypeTitle": "Données D3",
     "xpack.stackConnectors.components.d3security.eventTypeFieldLabel": "Type d'événement",
     "xpack.stackConnectors.components.d3security.invalidActionText": "Nom d'action non valide.",
     "xpack.stackConnectors.components.d3security.requiredActionText": "L'action est requise.",
diff --git a/x-pack/plugins/translations/translations/ja-JP.json b/x-pack/plugins/translations/translations/ja-JP.json
index 519c9f2a428a9..05a2e7a22a01c 100644
--- a/x-pack/plugins/translations/translations/ja-JP.json
+++ b/x-pack/plugins/translations/translations/ja-JP.json
@@ -11120,8 +11120,8 @@
     "xpack.apm.serviceIcons.service": "サービス",
     "xpack.apm.serviceIcons.serviceDetails.cloud.architecture": "アーキテクチャー",
     "xpack.apm.serviceIcons.serviceDetails.cloud.availabilityZoneLabel": "{zones, plural, other {可用性ゾーン}} ",
-    "xpack.apm.serviceIcons.serviceDetails.cloud.faasTriggerTypeLabel": "{triggerTypes, plural, other  {トリガータイプ}} ",
     "xpack.apm.serviceIcons.serviceDetails.cloud.functionNameLabel": "{functionNames, plural, other  {関数名}} ",
+    "xpack.apm.serviceIcons.serviceDetails.cloud.faasTriggerTypeLabel": "{triggerTypes, plural, other  {トリガータイプ}} ",
     "xpack.apm.serviceIcons.serviceDetails.cloud.machineTypesLabel": "{machineTypes, plural, other {コンピュータータイプ} }\n ",
     "xpack.apm.serviceIcons.serviceDetails.cloud.projectIdLabel": "プロジェクト ID",
     "xpack.apm.serviceIcons.serviceDetails.cloud.providerLabel": "クラウドプロバイダー",
@@ -27076,8 +27076,8 @@
     "xpack.maps.source.esSearch.descendingLabel": "降順",
     "xpack.maps.source.esSearch.extentFilterLabel": "マップの表示範囲でデータを動的にフィルタリング",
     "xpack.maps.source.esSearch.fieldNotFoundMsg": "インデックスパターン''{indexPatternName}''に''{fieldName}''が見つかりません。",
-    "xpack.maps.source.esSearch.geofieldLabel": "地理空間フィールド",
     "xpack.maps.source.esSearch.geoFieldLabel": "地理空間フィールド",
+    "xpack.maps.source.esSearch.geofieldLabel": "地理空間フィールド",
     "xpack.maps.source.esSearch.geoFieldTypeLabel": "地理空間フィールドタイプ",
     "xpack.maps.source.esSearch.indexOverOneLengthEditError": "データビューは複数のインデックスを参照しています。データビューごとに1つのインデックスのみが許可されています。",
     "xpack.maps.source.esSearch.indexZeroLengthEditError": "データビューはどのインデックスも参照していません。",
@@ -36537,8 +36537,8 @@
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.maxAlertsFieldLessThanWarning": "Kibanaで許可される最大数は、1回の実行につき、{maxNumber} {maxNumber, plural, other {アラート}}です。",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.nameFieldRequiredError": "名前が必要です。",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutrule.noteHelpText": "ルール調査ガイドを追加...",
-    "xpack.securitySolution.detectionEngine.createRule.stepAboutrule.setupHelpText": "ルールセットアップガイドを追加...",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.setupHelpText": "必要な統合、構成ステップ、ルールが正常に動作するために必要な他のすべての項目といった、ルール前提条件に関する指示を入力します。",
+    "xpack.securitySolution.detectionEngine.createRule.stepAboutrule.setupHelpText": "ルールセットアップガイドを追加...",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.setupLabel": "セットアップガイド",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.tagFieldEmptyError": "タグを空にすることはできません",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.threatIndicatorPathFieldEmptyError": "インジケータープレフィックスの無効化を空にすることはできません",
@@ -42176,8 +42176,8 @@
     "xpack.slo.sloEmbeddable.config.sloSelector.placeholder": "SLOを選択",
     "xpack.slo.sloEmbeddable.displayName": "SLO概要",
     "xpack.slo.sloEmbeddable.overview.sloNotFoundText": "SLOが削除されました。ウィジェットをダッシュボードから安全に削除できます。",
-    "xpack.slo.sloGridItem.targetFlexItemLabel": "目標{target}",
     "xpack.slo.sLOGridItem.targetFlexItemLabel": "目標{target}",
+    "xpack.slo.sloGridItem.targetFlexItemLabel": "目標{target}",
     "xpack.slo.sloGroupConfiguration.customFiltersLabel": "カスタムフィルター",
     "xpack.slo.sloGroupConfiguration.customFiltersOptional": "オプション",
     "xpack.slo.sloGroupConfiguration.customFilterText": "カスタムフィルター",
@@ -43619,8 +43619,8 @@
     "xpack.stackConnectors.components.casesWebhookxpack.stackConnectors.components.casesWebhook.connectorTypeTitle": "Webフック - ケース管理データ",
     "xpack.stackConnectors.components.d3security.bodyCodeEditorAriaLabel": "コードエディター",
     "xpack.stackConnectors.components.d3security.bodyFieldLabel": "本文",
-    "xpack.stackConnectors.components.d3security.connectorTypeTitle": "D3データ",
     "xpack.stackConnectors.components.d3Security.connectorTypeTitle": "D3セキュリティ",
+    "xpack.stackConnectors.components.d3security.connectorTypeTitle": "D3データ",
     "xpack.stackConnectors.components.d3security.eventTypeFieldLabel": "イベントタイプ",
     "xpack.stackConnectors.components.d3security.invalidActionText": "無効なアクション名です。",
     "xpack.stackConnectors.components.d3security.requiredActionText": "アクションが必要です。",
diff --git a/x-pack/plugins/translations/translations/zh-CN.json b/x-pack/plugins/translations/translations/zh-CN.json
index 328008ebf3952..ab9ce8edafe35 100644
--- a/x-pack/plugins/translations/translations/zh-CN.json
+++ b/x-pack/plugins/translations/translations/zh-CN.json
@@ -11139,8 +11139,8 @@
     "xpack.apm.serviceIcons.service": "服务",
     "xpack.apm.serviceIcons.serviceDetails.cloud.architecture": "架构",
     "xpack.apm.serviceIcons.serviceDetails.cloud.availabilityZoneLabel": "{zones, plural, other {可用性区域}} ",
-    "xpack.apm.serviceIcons.serviceDetails.cloud.faasTriggerTypeLabel": "{triggerTypes, plural, other {触发类型}} ",
     "xpack.apm.serviceIcons.serviceDetails.cloud.functionNameLabel": "{functionNames, plural, other {功能名称}} ",
+    "xpack.apm.serviceIcons.serviceDetails.cloud.faasTriggerTypeLabel": "{triggerTypes, plural, other {触发类型}} ",
     "xpack.apm.serviceIcons.serviceDetails.cloud.machineTypesLabel": "{machineTypes, plural, other {机器类型}} ",
     "xpack.apm.serviceIcons.serviceDetails.cloud.projectIdLabel": "项目 ID",
     "xpack.apm.serviceIcons.serviceDetails.cloud.providerLabel": "云服务提供商",
@@ -27108,8 +27108,8 @@
     "xpack.maps.source.esSearch.descendingLabel": "降序",
     "xpack.maps.source.esSearch.extentFilterLabel": "在可见地图区域中动态筛留数据",
     "xpack.maps.source.esSearch.fieldNotFoundMsg": "在索引模式“{indexPatternName}”中找不到“{fieldName}”。",
-    "xpack.maps.source.esSearch.geofieldLabel": "地理空间字段",
     "xpack.maps.source.esSearch.geoFieldLabel": "地理空间字段",
+    "xpack.maps.source.esSearch.geofieldLabel": "地理空间字段",
     "xpack.maps.source.esSearch.geoFieldTypeLabel": "地理空间字段类型",
     "xpack.maps.source.esSearch.indexOverOneLengthEditError": "您的数据视图指向多个索引。每个数据视图只允许一个索引。",
     "xpack.maps.source.esSearch.indexZeroLengthEditError": "您的数据视图未指向任何索引。",
@@ -36579,8 +36579,8 @@
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.maxAlertsFieldLessThanWarning": "每次规则运行时，Kibana 最多只允许 {maxNumber} 个{maxNumber, plural, other {告警}}。",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.nameFieldRequiredError": "名称必填。",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutrule.noteHelpText": "添加规则调查指南......",
-    "xpack.securitySolution.detectionEngine.createRule.stepAboutrule.setupHelpText": "添加规则设置指南......",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.setupHelpText": "提供有关规则先决条件的说明，如所需集成、配置步骤，以及规则正常运行所需的任何其他内容。",
+    "xpack.securitySolution.detectionEngine.createRule.stepAboutrule.setupHelpText": "添加规则设置指南......",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.setupLabel": "设置指南",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.tagFieldEmptyError": "标签不得为空",
     "xpack.securitySolution.detectionEngine.createRule.stepAboutRule.threatIndicatorPathFieldEmptyError": "指标前缀覆盖不得为空",
@@ -42220,8 +42220,8 @@
     "xpack.slo.sloEmbeddable.config.sloSelector.placeholder": "选择 SLO",
     "xpack.slo.sloEmbeddable.displayName": "SLO 概览",
     "xpack.slo.sloEmbeddable.overview.sloNotFoundText": "SLO 已删除。您可以放心从仪表板中删除小组件。",
-    "xpack.slo.sloGridItem.targetFlexItemLabel": "目标 {target}",
     "xpack.slo.sLOGridItem.targetFlexItemLabel": "目标 {target}",
+    "xpack.slo.sloGridItem.targetFlexItemLabel": "目标 {target}",
     "xpack.slo.sloGroupConfiguration.customFiltersLabel": "定制筛选",
     "xpack.slo.sloGroupConfiguration.customFiltersOptional": "可选",
     "xpack.slo.sloGroupConfiguration.customFilterText": "定制筛选",
@@ -43667,8 +43667,8 @@
     "xpack.stackConnectors.components.casesWebhookxpack.stackConnectors.components.casesWebhook.connectorTypeTitle": "Webhook - 案例管理数据",
     "xpack.stackConnectors.components.d3security.bodyCodeEditorAriaLabel": "代码编辑器",
     "xpack.stackConnectors.components.d3security.bodyFieldLabel": "正文",
-    "xpack.stackConnectors.components.d3security.connectorTypeTitle": "D3 数据",
     "xpack.stackConnectors.components.d3Security.connectorTypeTitle": "D3 Security",
+    "xpack.stackConnectors.components.d3security.connectorTypeTitle": "D3 数据",
     "xpack.stackConnectors.components.d3security.eventTypeFieldLabel": "事件类型",
     "xpack.stackConnectors.components.d3security.invalidActionText": "操作名称无效。",
     "xpack.stackConnectors.components.d3security.requiredActionText": "“操作”必填。",
diff --git a/x-pack/test/functional/apps/search_playground/playground_overview.ess.ts b/x-pack/test/functional/apps/search_playground/playground_overview.ess.ts
index a5013a92e72c0..31f8b32eec594 100644
--- a/x-pack/test/functional/apps/search_playground/playground_overview.ess.ts
+++ b/x-pack/test/functional/apps/search_playground/playground_overview.ess.ts
@@ -5,7 +5,6 @@
  * 2.0.
  */
 
-import type OpenAI from 'openai';
 import { FtrProviderContext } from '../../ftr_provider_context';
 import { createOpenAIConnector } from './utils/create_openai_connector';
 import { MachineLearningCommonAPIProvider } from '../../services/ml/common_api';
@@ -142,9 +141,7 @@ export default function (ftrContext: FtrProviderContext) {
           const conversationInterceptor = proxy.intercept(
             'conversation',
             (body) =>
-              (JSON.parse(body) as OpenAI.Chat.ChatCompletionCreateParamsNonStreaming).tools?.find(
-                (fn) => fn.function.name === 'title_conversation'
-              ) === undefined
+              body.tools?.find((fn) => fn.function.name === 'title_conversation') === undefined
           );
 
           await pageObjects.searchPlayground.PlaygroundChatPage.sendQuestion();
diff --git a/x-pack/test/observability_ai_assistant_api_integration/common/action_connectors.ts b/x-pack/test/observability_ai_assistant_api_integration/common/action_connectors.ts
new file mode 100644
index 0000000000000..b577ef03c5eb6
--- /dev/null
+++ b/x-pack/test/observability_ai_assistant_api_integration/common/action_connectors.ts
@@ -0,0 +1,63 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import { ToolingLog } from '@kbn/tooling-log';
+import { Agent } from 'supertest';
+
+export async function deleteActionConnector({
+  supertest,
+  connectorId,
+  log,
+}: {
+  supertest: Agent;
+  connectorId: string;
+  log: ToolingLog;
+}) {
+  try {
+    await supertest
+      .delete(`/api/actions/connector/${connectorId}`)
+      .set('kbn-xsrf', 'foo')
+      .expect(204);
+  } catch (e) {
+    log.error(`Failed to delete action connector with id ${connectorId} due to: ${e}`);
+    throw e;
+  }
+}
+
+export async function createProxyActionConnector({
+  log,
+  supertest,
+  port,
+}: {
+  log: ToolingLog;
+  supertest: Agent;
+  port: number;
+}) {
+  try {
+    const res = await supertest
+      .post('/api/actions/connector')
+      .set('kbn-xsrf', 'foo')
+      .send({
+        name: 'OpenAI Proxy',
+        connector_type_id: '.gen-ai',
+        config: {
+          apiProvider: 'OpenAI',
+          apiUrl: `http://localhost:${port}`,
+        },
+        secrets: {
+          apiKey: 'my-api-key',
+        },
+      })
+      .expect(200);
+
+    const connectorId = res.body.id as string;
+    return connectorId;
+  } catch (e) {
+    log.error(`Failed to create action connector due to: ${e}`);
+    throw e;
+  }
+}
diff --git a/x-pack/test/observability_ai_assistant_api_integration/common/config.ts b/x-pack/test/observability_ai_assistant_api_integration/common/config.ts
index acd6a6287d446..198fcefdc2bc8 100644
--- a/x-pack/test/observability_ai_assistant_api_integration/common/config.ts
+++ b/x-pack/test/observability_ai_assistant_api_integration/common/config.ts
@@ -51,6 +51,9 @@ export function createObservabilityAIAssistantAPIConfig({
     servers,
     services: {
       ...services,
+      getScopedApiClientForUsername: () => {
+        return (username: string) => getScopedApiClient(kibanaServer, username);
+      },
       apmSynthtraceEsClient: (context: InheritedFtrProviderContext) =>
         getApmSynthtraceEsClient(context, apmSynthtraceKibanaClient),
       observabilityAIAssistantAPIClient: async () => {
diff --git a/x-pack/test/observability_ai_assistant_api_integration/common/create_llm_proxy.ts b/x-pack/test/observability_ai_assistant_api_integration/common/create_llm_proxy.ts
index 2d01c7692e54f..7337fb8f6e5b2 100644
--- a/x-pack/test/observability_ai_assistant_api_integration/common/create_llm_proxy.ts
+++ b/x-pack/test/observability_ai_assistant_api_integration/common/create_llm_proxy.ts
@@ -9,20 +9,26 @@ import { ToolingLog } from '@kbn/tooling-log';
 import getPort from 'get-port';
 import http, { type Server } from 'http';
 import { once, pull } from 'lodash';
+import OpenAI from 'openai';
+import { TITLE_CONVERSATION_FUNCTION_NAME } from '@kbn/observability-ai-assistant-plugin/server/service/client/operators/get_generated_title';
 import { createOpenAiChunk } from './create_openai_chunk';
 
 type Request = http.IncomingMessage;
 type Response = http.ServerResponse<http.IncomingMessage> & { req: http.IncomingMessage };
 
-type RequestHandler = (request: Request, response: Response, body: string) => void;
+type RequestHandler = (
+  request: Request,
+  response: Response,
+  body: OpenAI.Chat.ChatCompletionCreateParamsNonStreaming
+) => void;
 
 interface RequestInterceptor {
   name: string;
-  when: (body: string) => boolean;
+  when: (body: OpenAI.Chat.ChatCompletionCreateParamsNonStreaming) => boolean;
 }
 
 export interface LlmResponseSimulator {
-  body: string;
+  body: OpenAI.Chat.ChatCompletionCreateParamsNonStreaming;
   status: (code: number) => Promise<void>;
   next: (
     msg:
@@ -40,10 +46,13 @@ export interface LlmResponseSimulator {
 
 export class LlmProxy {
   server: Server;
+  interval: NodeJS.Timeout;
 
   interceptors: Array<RequestInterceptor & { handle: RequestHandler }> = [];
 
   constructor(private readonly port: number, private readonly log: ToolingLog) {
+    this.interval = setInterval(() => this.log.debug(`LLM proxy listening on port ${port}`), 1000);
+
     this.server = http
       .createServer()
       .on('request', async (request, response) => {
@@ -62,7 +71,9 @@ export class LlmProxy {
           }
         }
 
-        response.writeHead(500, 'No interceptors found to handle request: ' + request.url);
+        const errorMessage = `No interceptors found to handle request: ${request.method} ${request.url}`;
+        this.log.error(`${errorMessage}. Messages: ${JSON.stringify(body.messages, null, 2)}`);
+        response.writeHead(500, { errorMessage, messages: JSON.stringify(body.messages) });
         response.end();
       })
       .on('error', (error) => {
@@ -80,6 +91,8 @@ export class LlmProxy {
   }
 
   close() {
+    this.log.debug(`Closing LLM Proxy on port ${this.port}`);
+    clearInterval(this.interval);
     this.server.close();
   }
 
@@ -87,6 +100,27 @@ export class LlmProxy {
     return Promise.all(this.interceptors);
   }
 
+  interceptConversation({
+    name = 'default_interceptor_conversation_name',
+    response,
+  }: {
+    name?: string;
+    response: string;
+  }) {
+    return this.intercept(name, (body) => !isFunctionTitleRequest(body), response);
+  }
+
+  interceptConversationTitle(title: string) {
+    return this.intercept('conversation_title', (body) => isFunctionTitleRequest(body), [
+      {
+        function_call: {
+          name: TITLE_CONVERSATION_FUNCTION_NAME,
+          arguments: JSON.stringify({ title }),
+        },
+      },
+    ]);
+  }
+
   intercept<
     TResponseChunks extends Array<Record<string, unknown>> | string | undefined = undefined
   >(
@@ -175,11 +209,13 @@ export class LlmProxy {
 
 export async function createLlmProxy(log: ToolingLog) {
   const port = await getPort({ port: getPort.makeRange(9000, 9100) });
-
+  log.debug(`Starting LLM Proxy on port ${port}`);
   return new LlmProxy(port, log);
 }
 
-async function getRequestBody(request: http.IncomingMessage): Promise<string> {
+async function getRequestBody(
+  request: http.IncomingMessage
+): Promise<OpenAI.Chat.ChatCompletionCreateParamsNonStreaming> {
   return new Promise((resolve, reject) => {
     let data = '';
 
@@ -188,7 +224,7 @@ async function getRequestBody(request: http.IncomingMessage): Promise<string> {
     });
 
     request.on('close', () => {
-      resolve(data);
+      resolve(JSON.parse(data));
     });
 
     request.on('error', (error) => {
@@ -196,3 +232,9 @@ async function getRequestBody(request: http.IncomingMessage): Promise<string> {
     });
   });
 }
+
+export function isFunctionTitleRequest(body: OpenAI.Chat.ChatCompletionCreateParamsNonStreaming) {
+  return (
+    body.tools?.find((fn) => fn.function.name === TITLE_CONVERSATION_FUNCTION_NAME) !== undefined
+  );
+}
diff --git a/x-pack/test/observability_ai_assistant_api_integration/common/observability_ai_assistant_api_client.ts b/x-pack/test/observability_ai_assistant_api_integration/common/observability_ai_assistant_api_client.ts
index 005815b38057a..ced1d24004e9b 100644
--- a/x-pack/test/observability_ai_assistant_api_integration/common/observability_ai_assistant_api_client.ts
+++ b/x-pack/test/observability_ai_assistant_api_integration/common/observability_ai_assistant_api_client.ts
@@ -15,9 +15,8 @@ import supertest from 'supertest';
 import { Subtract } from 'utility-types';
 import { format, UrlObject } from 'url';
 import { kbnTestConfig } from '@kbn/test';
-import { User } from './users/users';
 
-export async function getScopedApiClient(kibanaServer: UrlObject, username: User['username']) {
+export function getScopedApiClient(kibanaServer: UrlObject, username: string) {
   const { password } = kbnTestConfig.getUrlParts();
   const baseUrlWithAuth = format({
     ...kibanaServer,
@@ -27,6 +26,9 @@ export async function getScopedApiClient(kibanaServer: UrlObject, username: User
   return createObservabilityAIAssistantApiClient(supertest(baseUrlWithAuth));
 }
 
+export type ObservabilityAIAssistantApiClient = ReturnType<
+  typeof createObservabilityAIAssistantApiClient
+>;
 export function createObservabilityAIAssistantApiClient(st: supertest.Agent) {
   return <TEndpoint extends ObservabilityAIAssistantAPIEndpoint>(
     options: {
diff --git a/x-pack/test/observability_ai_assistant_api_integration/tests/chat/chat.spec.ts b/x-pack/test/observability_ai_assistant_api_integration/tests/chat/chat.spec.ts
index a9cf749b3d761..ffd1ad09c7ccd 100644
--- a/x-pack/test/observability_ai_assistant_api_integration/tests/chat/chat.spec.ts
+++ b/x-pack/test/observability_ai_assistant_api_integration/tests/chat/chat.spec.ts
@@ -10,6 +10,7 @@ import { MessageRole, type Message } from '@kbn/observability-ai-assistant-plugi
 import { PassThrough } from 'stream';
 import { createLlmProxy, LlmProxy } from '../../common/create_llm_proxy';
 import { FtrProviderContext } from '../../common/ftr_provider_context';
+import { createProxyActionConnector, deleteActionConnector } from '../../common/action_connectors';
 
 export default function ApiTest({ getService }: FtrProviderContext) {
   const supertest = getService('supertest');
@@ -41,28 +42,12 @@ export default function ApiTest({ getService }: FtrProviderContext) {
 
     before(async () => {
       proxy = await createLlmProxy(log);
-
-      const response = await supertest
-        .post('/api/actions/connector')
-        .set('kbn-xsrf', 'foo')
-        .send({
-          name: 'OpenAI',
-          connector_type_id: '.gen-ai',
-          config: {
-            apiProvider: 'OpenAI',
-            apiUrl: `http://localhost:${proxy.getPort()}`,
-          },
-          secrets: {
-            apiKey: 'my-api-key',
-          },
-        })
-        .expect(200);
-
-      connectorId = response.body.id;
+      connectorId = await createProxyActionConnector({ supertest, log, port: proxy.getPort() });
     });
 
-    after(() => {
+    after(async () => {
       proxy.close();
+      await deleteActionConnector({ supertest, connectorId, log });
     });
 
     it("returns a 4xx if the connector doesn't exist", async () => {
@@ -195,12 +180,5 @@ export default function ApiTest({ getService }: FtrProviderContext) {
         `Token limit reached. Token limit is 8192, but the current conversation has 11036 tokens.`
       );
     });
-
-    after(async () => {
-      await supertest
-        .delete(`/api/actions/connector/${connectorId}`)
-        .set('kbn-xsrf', 'foo')
-        .expect(204);
-    });
   });
 }
diff --git a/x-pack/test/observability_ai_assistant_api_integration/tests/complete/complete.spec.ts b/x-pack/test/observability_ai_assistant_api_integration/tests/complete/complete.spec.ts
index e159475f50523..1a79c3799f59b 100644
--- a/x-pack/test/observability_ai_assistant_api_integration/tests/complete/complete.spec.ts
+++ b/x-pack/test/observability_ai_assistant_api_integration/tests/complete/complete.spec.ts
@@ -7,7 +7,7 @@
 import { Response } from 'supertest';
 import { MessageRole, type Message } from '@kbn/observability-ai-assistant-plugin/common';
 import { omit, pick } from 'lodash';
-import { PassThrough, Readable } from 'stream';
+import { PassThrough } from 'stream';
 import expect from '@kbn/expect';
 import {
   ChatCompletionChunkEvent,
@@ -17,11 +17,21 @@ import {
   StreamingChatResponseEvent,
   StreamingChatResponseEventType,
 } from '@kbn/observability-ai-assistant-plugin/common/conversation_complete';
-import type OpenAI from 'openai';
 import { ObservabilityAIAssistantScreenContextRequest } from '@kbn/observability-ai-assistant-plugin/common/types';
-import { createLlmProxy, LlmProxy, LlmResponseSimulator } from '../../common/create_llm_proxy';
+import {
+  createLlmProxy,
+  isFunctionTitleRequest,
+  LlmProxy,
+  LlmResponseSimulator,
+} from '../../common/create_llm_proxy';
 import { createOpenAiChunk } from '../../common/create_openai_chunk';
 import { FtrProviderContext } from '../../common/ftr_provider_context';
+import {
+  decodeEvents,
+  getConversationCreatedEvent,
+  getConversationUpdatedEvent,
+} from '../conversations/helpers';
+import { createProxyActionConnector, deleteActionConnector } from '../../common/action_connectors';
 
 export default function ApiTest({ getService }: FtrProviderContext) {
   const supertest = getService('supertest');
@@ -105,33 +115,12 @@ export default function ApiTest({ getService }: FtrProviderContext) {
 
     before(async () => {
       proxy = await createLlmProxy(log);
-
-      const response = await supertest
-        .post('/api/actions/connector')
-        .set('kbn-xsrf', 'foo')
-        .send({
-          name: 'OpenAI Proxy',
-          connector_type_id: '.gen-ai',
-          config: {
-            apiProvider: 'OpenAI',
-            apiUrl: `http://localhost:${proxy.getPort()}`,
-          },
-          secrets: {
-            apiKey: 'my-api-key',
-          },
-        })
-        .expect(200);
-
-      connectorId = response.body.id;
+      connectorId = await createProxyActionConnector({ supertest, log, port: proxy.getPort() });
     });
 
     after(async () => {
-      await supertest
-        .delete(`/api/actions/connector/${connectorId}`)
-        .set('kbn-xsrf', 'foo')
-        .expect(204);
-
       proxy.close();
+      await deleteActionConnector({ supertest, connectorId, log });
     });
 
     it('returns a streaming response from the server', async () => {
@@ -390,20 +379,6 @@ export default function ApiTest({ getService }: FtrProviderContext) {
       let conversationCreatedEvent: ConversationCreateEvent;
       let conversationUpdatedEvent: ConversationUpdateEvent;
 
-      function getConversationCreatedEvent(body: Readable | string) {
-        const decodedEvents = decodeEvents(body);
-        return decodedEvents.find(
-          (event) => event.type === StreamingChatResponseEventType.ConversationCreate
-        ) as ConversationCreateEvent;
-      }
-
-      function getConversationUpdatedEvent(body: Readable | string) {
-        const decodedEvents = decodeEvents(body);
-        return decodedEvents.find(
-          (event) => event.type === StreamingChatResponseEventType.ConversationUpdate
-        ) as ConversationUpdateEvent;
-      }
-
       before(async () => {
         proxy
           .intercept('conversation_title', (body) => isFunctionTitleRequest(body), [
@@ -511,16 +486,3 @@ export default function ApiTest({ getService }: FtrProviderContext) {
     it.skip('executes a function', async () => {});
   });
 }
-
-function decodeEvents(body: Readable | string) {
-  return String(body)
-    .split('\n')
-    .map((line) => line.trim())
-    .filter(Boolean)
-    .map((line) => JSON.parse(line) as StreamingChatResponseEvent);
-}
-
-function isFunctionTitleRequest(body: string) {
-  const parsedBody = JSON.parse(body) as OpenAI.Chat.ChatCompletionCreateParamsNonStreaming;
-  return parsedBody.tools?.find((fn) => fn.function.name === 'title_conversation') !== undefined;
-}
diff --git a/x-pack/test/observability_ai_assistant_api_integration/tests/complete/functions/elasticsearch.spec.ts b/x-pack/test/observability_ai_assistant_api_integration/tests/complete/functions/elasticsearch.spec.ts
index 559f21e944011..961afefb0748f 100644
--- a/x-pack/test/observability_ai_assistant_api_integration/tests/complete/functions/elasticsearch.spec.ts
+++ b/x-pack/test/observability_ai_assistant_api_integration/tests/complete/functions/elasticsearch.spec.ts
@@ -10,14 +10,13 @@ import expect from '@kbn/expect';
 import { apm, timerange } from '@kbn/apm-synthtrace-client';
 import { ApmSynthtraceEsClient } from '@kbn/apm-synthtrace';
 import { ELASTICSEARCH_FUNCTION_NAME } from '@kbn/observability-ai-assistant-plugin/server/functions/elasticsearch';
-import { LlmProxy } from '../../../common/create_llm_proxy';
+import { LlmProxy, createLlmProxy } from '../../../common/create_llm_proxy';
 import { FtrProviderContext } from '../../../common/ftr_provider_context';
+import { getMessageAddedEvents, invokeChatCompleteWithFunctionRequest } from './helpers';
 import {
-  createLLMProxyConnector,
-  deleteLLMProxyConnector,
-  getMessageAddedEvents,
-  invokeChatCompleteWithFunctionRequest,
-} from './helpers';
+  createProxyActionConnector,
+  deleteActionConnector,
+} from '../../../common/action_connectors';
 
 export default function ApiTest({ getService }: FtrProviderContext) {
   const supertest = getService('supertest');
@@ -31,7 +30,12 @@ export default function ApiTest({ getService }: FtrProviderContext) {
     let events: MessageAddEvent[];
 
     before(async () => {
-      ({ connectorId, proxy } = await createLLMProxyConnector({ log, supertest }));
+      proxy = await createLlmProxy(log);
+      connectorId = await createProxyActionConnector({ supertest, log, port: proxy.getPort() });
+
+      // intercept the LLM request and return a fixed response
+      proxy.intercept('conversation', () => true, 'Hello from LLM Proxy').completeAfterIntercept();
+
       await generateApmData(apmSynthtraceEsClient);
 
       const responseBody = await invokeChatCompleteWithFunctionRequest({
@@ -63,7 +67,8 @@ export default function ApiTest({ getService }: FtrProviderContext) {
     });
 
     after(async () => {
-      await deleteLLMProxyConnector({ supertest, connectorId, proxy });
+      proxy.close();
+      await deleteActionConnector({ supertest, connectorId, log });
       await apmSynthtraceEsClient.clean();
     });
 
diff --git a/x-pack/test/observability_ai_assistant_api_integration/tests/complete/functions/helpers.ts b/x-pack/test/observability_ai_assistant_api_integration/tests/complete/functions/helpers.ts
index f4323c96e3eff..a32c22abcf7aa 100644
--- a/x-pack/test/observability_ai_assistant_api_integration/tests/complete/functions/helpers.ts
+++ b/x-pack/test/observability_ai_assistant_api_integration/tests/complete/functions/helpers.ts
@@ -11,11 +11,8 @@ import {
   MessageRole,
   StreamingChatResponseEvent,
 } from '@kbn/observability-ai-assistant-plugin/common';
-import { ToolingLog } from '@kbn/tooling-log';
-import { Agent } from 'supertest';
 import { Readable } from 'stream';
 import { CreateTest } from '../../../common/config';
-import { createLlmProxy, LlmProxy } from '../../../common/create_llm_proxy';
 
 function decodeEvents(body: Readable | string) {
   return String(body)
@@ -31,57 +28,6 @@ export function getMessageAddedEvents(body: Readable | string) {
   );
 }
 
-export async function createLLMProxyConnector({
-  log,
-  supertest,
-}: {
-  log: ToolingLog;
-  supertest: Agent;
-}) {
-  const proxy = await createLlmProxy(log);
-
-  // intercept the LLM request and return a fixed response
-  proxy.intercept('conversation', () => true, 'Hello from LLM Proxy').completeAfterIntercept();
-
-  const response = await supertest
-    .post('/api/actions/connector')
-    .set('kbn-xsrf', 'foo')
-    .send({
-      name: 'OpenAI Proxy',
-      connector_type_id: '.gen-ai',
-      config: {
-        apiProvider: 'OpenAI',
-        apiUrl: `http://localhost:${proxy.getPort()}`,
-      },
-      secrets: {
-        apiKey: 'my-api-key',
-      },
-    })
-    .expect(200);
-
-  return {
-    proxy,
-    connectorId: response.body.id,
-  };
-}
-
-export async function deleteLLMProxyConnector({
-  supertest,
-  connectorId,
-  proxy,
-}: {
-  supertest: Agent;
-  connectorId: string;
-  proxy: LlmProxy;
-}) {
-  await supertest
-    .delete(`/api/actions/connector/${connectorId}`)
-    .set('kbn-xsrf', 'foo')
-    .expect(204);
-
-  proxy.close();
-}
-
 export async function invokeChatCompleteWithFunctionRequest({
   connectorId,
   observabilityAIAssistantAPIClient,
diff --git a/x-pack/test/observability_ai_assistant_api_integration/tests/complete/functions/summarize.spec.ts b/x-pack/test/observability_ai_assistant_api_integration/tests/complete/functions/summarize.spec.ts
index 0cda45a1a4253..8f312219f2e49 100644
--- a/x-pack/test/observability_ai_assistant_api_integration/tests/complete/functions/summarize.spec.ts
+++ b/x-pack/test/observability_ai_assistant_api_integration/tests/complete/functions/summarize.spec.ts
@@ -7,13 +7,13 @@
 
 import { MessageRole } from '@kbn/observability-ai-assistant-plugin/common';
 import expect from '@kbn/expect';
-import { LlmProxy } from '../../../common/create_llm_proxy';
+import { LlmProxy, createLlmProxy } from '../../../common/create_llm_proxy';
 import { FtrProviderContext } from '../../../common/ftr_provider_context';
+import { invokeChatCompleteWithFunctionRequest } from './helpers';
 import {
-  createLLMProxyConnector,
-  deleteLLMProxyConnector,
-  invokeChatCompleteWithFunctionRequest,
-} from './helpers';
+  createProxyActionConnector,
+  deleteActionConnector,
+} from '../../../common/action_connectors';
 
 export default function ApiTest({ getService }: FtrProviderContext) {
   const supertest = getService('supertest');
@@ -26,7 +26,11 @@ export default function ApiTest({ getService }: FtrProviderContext) {
     let connectorId: string;
 
     before(async () => {
-      ({ connectorId, proxy } = await createLLMProxyConnector({ log, supertest }));
+      proxy = await createLlmProxy(log);
+      connectorId = await createProxyActionConnector({ supertest, log, port: proxy.getPort() });
+
+      // intercept the LLM request and return a fixed response
+      proxy.intercept('conversation', () => true, 'Hello from LLM Proxy').completeAfterIntercept();
 
       await invokeChatCompleteWithFunctionRequest({
         connectorId,
@@ -48,7 +52,8 @@ export default function ApiTest({ getService }: FtrProviderContext) {
     });
 
     after(async () => {
-      await deleteLLMProxyConnector({ supertest, connectorId, proxy });
+      proxy.close();
+      await deleteActionConnector({ supertest, connectorId, log });
     });
 
     it('persists entry in knowledge base', async () => {
diff --git a/x-pack/test/observability_ai_assistant_api_integration/tests/connectors/connectors.spec.ts b/x-pack/test/observability_ai_assistant_api_integration/tests/connectors/connectors.spec.ts
index d334251d9114e..e8363ba41513b 100644
--- a/x-pack/test/observability_ai_assistant_api_integration/tests/connectors/connectors.spec.ts
+++ b/x-pack/test/observability_ai_assistant_api_integration/tests/connectors/connectors.spec.ts
@@ -8,10 +8,12 @@
 import expect from '@kbn/expect';
 import type { Agent as SuperTestAgent } from 'supertest';
 import { FtrProviderContext } from '../../common/ftr_provider_context';
+import { createProxyActionConnector, deleteActionConnector } from '../../common/action_connectors';
 
 export default function ApiTest({ getService }: FtrProviderContext) {
   const observabilityAIAssistantAPIClient = getService('observabilityAIAssistantAPIClient');
   const supertest = getService('supertest');
+  const log = getService('log');
 
   describe('List connectors', () => {
     before(async () => {
@@ -39,21 +41,7 @@ export default function ApiTest({ getService }: FtrProviderContext) {
     });
 
     it("returns the gen ai connector if it's been created", async () => {
-      const connectorCreateResponse = await supertest
-        .post('/api/actions/connector')
-        .set('kbn-xsrf', 'foo')
-        .send({
-          name: 'OpenAI',
-          connector_type_id: '.gen-ai',
-          config: {
-            apiProvider: 'OpenAI',
-            apiUrl: 'http://localhost:9200',
-          },
-          secrets: {
-            apiKey: 'my-api-key',
-          },
-        })
-        .expect(200);
+      const connectorId = await createProxyActionConnector({ supertest, log, port: 1234 });
 
       const res = await observabilityAIAssistantAPIClient.editorUser({
         endpoint: 'GET /internal/observability_ai_assistant/connectors',
@@ -61,12 +49,7 @@ export default function ApiTest({ getService }: FtrProviderContext) {
 
       expect(res.body.length).to.be(1);
 
-      const connectorId = connectorCreateResponse.body.id;
-
-      await supertest
-        .delete(`/api/actions/connector/${connectorId}`)
-        .set('kbn-xsrf', 'foo')
-        .expect(204);
+      await deleteActionConnector({ supertest, connectorId, log });
     });
   });
 }
diff --git a/x-pack/test/observability_ai_assistant_api_integration/tests/conversations/helpers.ts b/x-pack/test/observability_ai_assistant_api_integration/tests/conversations/helpers.ts
new file mode 100644
index 0000000000000..2e5d359ed1e78
--- /dev/null
+++ b/x-pack/test/observability_ai_assistant_api_integration/tests/conversations/helpers.ts
@@ -0,0 +1,52 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import { Readable } from 'stream';
+import {
+  ConversationCreateEvent,
+  ConversationUpdateEvent,
+  StreamingChatResponseEvent,
+  StreamingChatResponseEventType,
+} from '@kbn/observability-ai-assistant-plugin/common/conversation_complete';
+
+export function decodeEvents(body: Readable | string) {
+  return String(body)
+    .split('\n')
+    .map((line) => line.trim())
+    .filter(Boolean)
+    .map((line) => JSON.parse(line) as StreamingChatResponseEvent);
+}
+
+export function getConversationCreatedEvent(body: Readable | string) {
+  const decodedEvents = decodeEvents(body);
+  const conversationCreatedEvent = decodedEvents.find(
+    (event) => event.type === StreamingChatResponseEventType.ConversationCreate
+  ) as ConversationCreateEvent;
+
+  if (!conversationCreatedEvent) {
+    throw new Error(
+      `No conversation created event found: ${JSON.stringify(decodedEvents, null, 2)}`
+    );
+  }
+
+  return conversationCreatedEvent;
+}
+
+export function getConversationUpdatedEvent(body: Readable | string) {
+  const decodedEvents = decodeEvents(body);
+  const conversationUpdatedEvent = decodedEvents.find(
+    (event) => event.type === StreamingChatResponseEventType.ConversationUpdate
+  ) as ConversationUpdateEvent;
+
+  if (!conversationUpdatedEvent) {
+    throw new Error(
+      `No conversation created event found: ${JSON.stringify(decodedEvents, null, 2)}`
+    );
+  }
+
+  return conversationUpdatedEvent;
+}
diff --git a/x-pack/test/observability_ai_assistant_api_integration/tests/knowledge_base/helpers.ts b/x-pack/test/observability_ai_assistant_api_integration/tests/knowledge_base/helpers.ts
index 1d9a9170e56ea..1818203f737c0 100644
--- a/x-pack/test/observability_ai_assistant_api_integration/tests/knowledge_base/helpers.ts
+++ b/x-pack/test/observability_ai_assistant_api_integration/tests/knowledge_base/helpers.ts
@@ -5,6 +5,7 @@
  * 2.0.
  */
 
+import { Client } from '@elastic/elasticsearch';
 import { MachineLearningProvider } from '../../../api_integration/services/ml';
 import { SUPPORTED_TRAINED_MODELS } from '../../../functional/services/ml/api';
 
@@ -23,9 +24,32 @@ export async function createKnowledgeBaseModel(ml: ReturnType<typeof MachineLear
   await ml.api.importTrainedModel(TINY_ELSER.name, TINY_ELSER.id, config);
   await ml.api.assureMlStatsIndexExists();
 }
+
 export async function deleteKnowledgeBaseModel(ml: ReturnType<typeof MachineLearningProvider>) {
   await ml.api.stopTrainedModelDeploymentES(TINY_ELSER.id, true);
   await ml.api.deleteTrainedModelES(TINY_ELSER.id);
   await ml.api.cleanMlIndices();
   await ml.testResources.cleanMLSavedObjects();
 }
+
+export async function clearKnowledgeBase(es: Client) {
+  const KB_INDEX = '.kibana-observability-ai-assistant-kb-*';
+
+  return es.deleteByQuery({
+    index: KB_INDEX,
+    conflicts: 'proceed',
+    query: { match_all: {} },
+    refresh: true,
+  });
+}
+
+export async function clearConversations(es: Client) {
+  const KB_INDEX = '.kibana-observability-ai-assistant-conversations-*';
+
+  return es.deleteByQuery({
+    index: KB_INDEX,
+    conflicts: 'proceed',
+    query: { match_all: {} },
+    refresh: true,
+  });
+}
diff --git a/x-pack/test/observability_ai_assistant_api_integration/tests/knowledge_base/knowledge_base.spec.ts b/x-pack/test/observability_ai_assistant_api_integration/tests/knowledge_base/knowledge_base.spec.ts
index 74ba11ce2eb9e..c8881e82e43bb 100644
--- a/x-pack/test/observability_ai_assistant_api_integration/tests/knowledge_base/knowledge_base.spec.ts
+++ b/x-pack/test/observability_ai_assistant_api_integration/tests/knowledge_base/knowledge_base.spec.ts
@@ -7,19 +7,13 @@
 
 import expect from '@kbn/expect';
 import { FtrProviderContext } from '../../common/ftr_provider_context';
-import { createKnowledgeBaseModel, deleteKnowledgeBaseModel } from './helpers';
-
-interface KnowledgeBaseEntry {
-  id: string;
-  text: string;
-}
+import { clearKnowledgeBase, createKnowledgeBaseModel, deleteKnowledgeBaseModel } from './helpers';
 
 export default function ApiTest({ getService }: FtrProviderContext) {
   const ml = getService('ml');
   const es = getService('es');
 
   const observabilityAIAssistantAPIClient = getService('observabilityAIAssistantAPIClient');
-  const KB_INDEX = '.kibana-observability-ai-assistant-kb-*';
 
   describe('Knowledge base', () => {
     before(async () => {
@@ -106,10 +100,9 @@ export default function ApiTest({ getService }: FtrProviderContext) {
             },
           })
           .expect(200);
-        expect(
-          res.body.entries.filter((entry: KnowledgeBaseEntry) => entry.id.startsWith('my-doc-id'))
-            .length
-        ).to.eql(0);
+        expect(res.body.entries.filter((entry) => entry.id.startsWith('my-doc-id')).length).to.eql(
+          0
+        );
       });
 
       it('returns 500 on delete not found', async () => {
@@ -126,20 +119,12 @@ export default function ApiTest({ getService }: FtrProviderContext) {
     });
     describe('when managing multiple entries', () => {
       before(async () => {
-        es.deleteByQuery({
-          index: KB_INDEX,
-          conflicts: 'proceed',
-          query: { match_all: {} },
-        });
+        await clearKnowledgeBase(es);
       });
       afterEach(async () => {
-        es.deleteByQuery({
-          index: KB_INDEX,
-          conflicts: 'proceed',
-          query: { match_all: {} },
-        });
+        await clearKnowledgeBase(es);
       });
-      const knowledgeBaseEntries: KnowledgeBaseEntry[] = [
+      const knowledgeBaseEntries = [
         {
           id: 'my_doc_a',
           text: 'My content a',
@@ -173,10 +158,7 @@ export default function ApiTest({ getService }: FtrProviderContext) {
             },
           })
           .expect(200);
-        expect(
-          res.body.entries.filter((entry: KnowledgeBaseEntry) => entry.id.startsWith('my_doc'))
-            .length
-        ).to.eql(3);
+        expect(res.body.entries.filter((entry) => entry.id.startsWith('my_doc')).length).to.eql(3);
       });
 
       it('allows sorting', async () => {
@@ -200,9 +182,7 @@ export default function ApiTest({ getService }: FtrProviderContext) {
           })
           .expect(200);
 
-        const entries = res.body.entries.filter((entry: KnowledgeBaseEntry) =>
-          entry.id.startsWith('my_doc')
-        );
+        const entries = res.body.entries.filter((entry) => entry.id.startsWith('my_doc'));
         expect(entries[0].id).to.eql('my_doc_c');
         expect(entries[1].id).to.eql('my_doc_b');
         expect(entries[2].id).to.eql('my_doc_a');
@@ -221,9 +201,7 @@ export default function ApiTest({ getService }: FtrProviderContext) {
           })
           .expect(200);
 
-        const entriesAsc = resAsc.body.entries.filter((entry: KnowledgeBaseEntry) =>
-          entry.id.startsWith('my_doc')
-        );
+        const entriesAsc = resAsc.body.entries.filter((entry) => entry.id.startsWith('my_doc'));
         expect(entriesAsc[0].id).to.eql('my_doc_a');
         expect(entriesAsc[1].id).to.eql('my_doc_b');
         expect(entriesAsc[2].id).to.eql('my_doc_c');
diff --git a/x-pack/test/observability_ai_assistant_api_integration/tests/knowledge_base/knowledge_base_user_instructions.spec.ts b/x-pack/test/observability_ai_assistant_api_integration/tests/knowledge_base/knowledge_base_user_instructions.spec.ts
new file mode 100644
index 0000000000000..4cad8079dc0b2
--- /dev/null
+++ b/x-pack/test/observability_ai_assistant_api_integration/tests/knowledge_base/knowledge_base_user_instructions.spec.ts
@@ -0,0 +1,319 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License
+ * 2.0; you may not use this file except in compliance with the Elastic License
+ * 2.0.
+ */
+
+import expect from '@kbn/expect';
+import { kbnTestConfig } from '@kbn/test';
+import { sortBy } from 'lodash';
+import { Message, MessageRole } from '@kbn/observability-ai-assistant-plugin/common';
+import { CONTEXT_FUNCTION_NAME } from '@kbn/observability-ai-assistant-plugin/server/functions/context';
+import { FtrProviderContext } from '../../common/ftr_provider_context';
+import {
+  clearConversations,
+  clearKnowledgeBase,
+  createKnowledgeBaseModel,
+  deleteKnowledgeBaseModel,
+} from './helpers';
+import { getConversationCreatedEvent } from '../conversations/helpers';
+import { LlmProxy, createLlmProxy } from '../../common/create_llm_proxy';
+import { createProxyActionConnector, deleteActionConnector } from '../../common/action_connectors';
+
+export default function ApiTest({ getService }: FtrProviderContext) {
+  const observabilityAIAssistantAPIClient = getService('observabilityAIAssistantAPIClient');
+  const getScopedApiClientForUsername = getService('getScopedApiClientForUsername');
+  const security = getService('security');
+  const supertest = getService('supertest');
+  const es = getService('es');
+  const ml = getService('ml');
+  const log = getService('log');
+
+  describe('Knowledge base user instructions', () => {
+    const userJohn = 'john';
+
+    before(async () => {
+      // create user
+      const password = kbnTestConfig.getUrlParts().password!;
+      await security.user.create(userJohn, { password, roles: ['editor'] });
+      await createKnowledgeBaseModel(ml);
+
+      await observabilityAIAssistantAPIClient
+        .editorUser({ endpoint: 'POST /internal/observability_ai_assistant/kb/setup' })
+        .expect(200);
+    });
+
+    after(async () => {
+      await deleteKnowledgeBaseModel(ml);
+      await security.user.delete(userJohn);
+      await clearKnowledgeBase(es);
+      await clearConversations(es);
+    });
+
+    describe('when creating private and public user instructions', () => {
+      before(async () => {
+        await clearKnowledgeBase(es);
+
+        const promises = [
+          {
+            username: 'editor',
+            isPublic: true,
+          },
+          {
+            username: 'editor',
+            isPublic: false,
+          },
+          {
+            username: userJohn,
+            isPublic: true,
+          },
+          {
+            username: userJohn,
+            isPublic: false,
+          },
+        ].map(async ({ username, isPublic }) => {
+          const visibility = isPublic ? 'Public' : 'Private';
+          await getScopedApiClientForUsername(username)({
+            endpoint: 'PUT /internal/observability_ai_assistant/kb/user_instructions',
+            params: {
+              body: {
+                id: `${visibility.toLowerCase()}-doc-from-${username}`,
+                text: `${visibility} user instruction from "${username}"`,
+                public: isPublic,
+              },
+            },
+          }).expect(200);
+        });
+
+        await Promise.all(promises);
+      });
+
+      it('"editor" can retrieve their own private instructions and the public instruction', async () => {
+        const res = await observabilityAIAssistantAPIClient.editorUser({
+          endpoint: 'GET /internal/observability_ai_assistant/kb/user_instructions',
+        });
+        const instructions = res.body.userInstructions;
+
+        const sortByDocId = (data: any) => sortBy(data, 'doc_id');
+        expect(sortByDocId(instructions)).to.eql(
+          sortByDocId([
+            {
+              doc_id: 'private-doc-from-editor',
+              public: false,
+              text: 'Private user instruction from "editor"',
+            },
+            {
+              doc_id: 'public-doc-from-editor',
+              public: true,
+              text: 'Public user instruction from "editor"',
+            },
+            {
+              doc_id: 'public-doc-from-john',
+              public: true,
+              text: 'Public user instruction from "john"',
+            },
+          ])
+        );
+      });
+
+      it('"john" can retrieve their own private instructions and the public instruction', async () => {
+        const res = await getScopedApiClientForUsername(userJohn)({
+          endpoint: 'GET /internal/observability_ai_assistant/kb/user_instructions',
+        });
+        const instructions = res.body.userInstructions;
+
+        const sortByDocId = (data: any) => sortBy(data, 'doc_id');
+        expect(sortByDocId(instructions)).to.eql(
+          sortByDocId([
+            {
+              doc_id: 'public-doc-from-editor',
+              public: true,
+              text: 'Public user instruction from "editor"',
+            },
+            {
+              doc_id: 'public-doc-from-john',
+              public: true,
+              text: 'Public user instruction from "john"',
+            },
+            {
+              doc_id: 'private-doc-from-john',
+              public: false,
+              text: 'Private user instruction from "john"',
+            },
+          ])
+        );
+      });
+    });
+
+    describe('when updating an existing user instructions', () => {
+      before(async () => {
+        await clearKnowledgeBase(es);
+
+        await observabilityAIAssistantAPIClient
+          .editorUser({
+            endpoint: 'PUT /internal/observability_ai_assistant/kb/user_instructions',
+            params: {
+              body: {
+                id: 'doc-to-update',
+                text: 'Initial text',
+                public: true,
+              },
+            },
+          })
+          .expect(200);
+
+        await observabilityAIAssistantAPIClient
+          .editorUser({
+            endpoint: 'PUT /internal/observability_ai_assistant/kb/user_instructions',
+            params: {
+              body: {
+                id: 'doc-to-update',
+                text: 'Updated text',
+                public: false,
+              },
+            },
+          })
+          .expect(200);
+      });
+
+      it('updates the user instruction', async () => {
+        const res = await observabilityAIAssistantAPIClient.editorUser({
+          endpoint: 'GET /internal/observability_ai_assistant/kb/user_instructions',
+        });
+        const instructions = res.body.userInstructions;
+
+        expect(instructions).to.eql([
+          {
+            doc_id: 'doc-to-update',
+            text: 'Updated text',
+            public: false,
+          },
+        ]);
+      });
+    });
+
+    describe('when a user instruction exist and a conversation is created', () => {
+      let proxy: LlmProxy;
+      let connectorId: string;
+
+      const userInstructionText =
+        'Be polite and use language that is easy to understand. Never disagree with the user.';
+
+      async function getConversationForUser(username: string) {
+        const apiClient = getScopedApiClientForUsername(username);
+
+        // the user instruction is always created by "editor" user
+        await observabilityAIAssistantAPIClient
+          .editorUser({
+            endpoint: 'PUT /internal/observability_ai_assistant/kb/user_instructions',
+            params: {
+              body: {
+                id: 'private-instruction-about-language',
+                text: userInstructionText,
+                public: false,
+              },
+            },
+          })
+          .expect(200);
+
+        const interceptPromises = [
+          proxy.interceptConversationTitle('LLM-generated title').completeAfterIntercept(),
+          proxy
+            .interceptConversation({ name: 'conversation', response: 'I, the LLM, hear you!' })
+            .completeAfterIntercept(),
+        ];
+
+        const messages: Message[] = [
+          {
+            '@timestamp': new Date().toISOString(),
+            message: {
+              role: MessageRole.System,
+              content: 'You are a helpful assistant',
+            },
+          },
+          {
+            '@timestamp': new Date().toISOString(),
+            message: {
+              role: MessageRole.User,
+              content: 'Today we will be testing user instructions!',
+            },
+          },
+        ];
+
+        const createResponse = await apiClient({
+          endpoint: 'POST /internal/observability_ai_assistant/chat/complete',
+          params: {
+            body: {
+              messages,
+              connectorId,
+              persist: true,
+              screenContexts: [],
+            },
+          },
+        }).expect(200);
+
+        await proxy.waitForAllInterceptorsSettled();
+        const conversationCreatedEvent = getConversationCreatedEvent(createResponse.body);
+        const conversationId = conversationCreatedEvent.conversation.id;
+
+        const res = await apiClient({
+          endpoint: 'GET /internal/observability_ai_assistant/conversation/{conversationId}',
+          params: {
+            path: {
+              conversationId,
+            },
+          },
+        });
+
+        // wait for all interceptors to be settled
+        await Promise.all(interceptPromises);
+
+        const conversation = res.body;
+        return conversation;
+      }
+
+      before(async () => {
+        proxy = await createLlmProxy(log);
+        connectorId = await createProxyActionConnector({ supertest, log, port: proxy.getPort() });
+      });
+
+      after(async () => {
+        proxy.close();
+        await deleteActionConnector({ supertest, connectorId, log });
+      });
+
+      it('adds the instruction to the system prompt', async () => {
+        const conversation = await getConversationForUser('editor');
+        const systemMessage = conversation.messages.find(
+          (message) => message.message.role === MessageRole.System
+        )!;
+        expect(systemMessage.message.content).to.contain(userInstructionText);
+      });
+
+      it('does not add the instruction to the context', async () => {
+        const conversation = await getConversationForUser('editor');
+        const contextMessage = conversation.messages.find(
+          (message) => message.message.name === CONTEXT_FUNCTION_NAME
+        );
+
+        // there should be no suggestions with the user instruction
+        expect(contextMessage?.message.content).to.not.contain(userInstructionText);
+        expect(contextMessage?.message.data).to.not.contain(userInstructionText);
+
+        // there should be no suggestions at all
+        expect(JSON.parse(contextMessage?.message.data!).suggestions.length).to.be(0);
+      });
+
+      it('does not add the instruction conversation for other users', async () => {
+        const conversation = await getConversationForUser('john');
+        const systemMessage = conversation.messages.find(
+          (message) => message.message.role === MessageRole.System
+        )!;
+
+        expect(systemMessage.message.content).to.not.contain(userInstructionText);
+        expect(conversation.messages.length).to.be(5);
+      });
+    });
+  });
+}
diff --git a/x-pack/test/observability_ai_assistant_api_integration/tests/public_complete/public_complete.spec.ts b/x-pack/test/observability_ai_assistant_api_integration/tests/public_complete/public_complete.spec.ts
index f496e42868ac8..344b387bdde38 100644
--- a/x-pack/test/observability_ai_assistant_api_integration/tests/public_complete/public_complete.spec.ts
+++ b/x-pack/test/observability_ai_assistant_api_integration/tests/public_complete/public_complete.spec.ts
@@ -10,18 +10,23 @@ import {
   MessageRole,
   type Message,
 } from '@kbn/observability-ai-assistant-plugin/common';
-import { StreamingChatResponseEvent } from '@kbn/observability-ai-assistant-plugin/common/conversation_complete';
+import { type StreamingChatResponseEvent } from '@kbn/observability-ai-assistant-plugin/common/conversation_complete';
 import { pick } from 'lodash';
 import type OpenAI from 'openai';
-import { Response } from 'supertest';
-import { createLlmProxy, LlmProxy, LlmResponseSimulator } from '../../common/create_llm_proxy';
+import { type AdHocInstruction } from '@kbn/observability-ai-assistant-plugin/common/types';
+import {
+  createLlmProxy,
+  isFunctionTitleRequest,
+  LlmProxy,
+  LlmResponseSimulator,
+} from '../../common/create_llm_proxy';
 import { FtrProviderContext } from '../../common/ftr_provider_context';
+import { createProxyActionConnector, deleteActionConnector } from '../../common/action_connectors';
 
 export default function ApiTest({ getService }: FtrProviderContext) {
   const supertest = getService('supertest');
   const log = getService('log');
-
-  const PUBLIC_COMPLETE_API_URL = `/api/observability_ai_assistant/chat/complete`;
+  const observabilityAIAssistantAPIClient = getService('observabilityAIAssistantAPIClient');
 
   const messages: Message[] = [
     {
@@ -46,8 +51,8 @@ export default function ApiTest({ getService }: FtrProviderContext) {
 
     interface RequestOptions {
       actions?: Array<Pick<FunctionDefinition, 'name' | 'description' | 'parameters'>>;
-      instructions?: string[];
-      format?: 'openai';
+      instructions?: AdHocInstruction[];
+      format?: 'openai' | 'default';
     }
 
     type ConversationSimulatorCallback = (
@@ -55,7 +60,7 @@ export default function ApiTest({ getService }: FtrProviderContext) {
     ) => Promise<void>;
 
     async function getResponseBody(
-      { actions, instructions, format }: RequestOptions,
+      { actions, instructions, format = 'default' }: RequestOptions,
       conversationSimulatorCallback: ConversationSimulatorCallback
     ) {
       const titleInterceptor = proxy.intercept('title', (body) => isFunctionTitleRequest(body));
@@ -65,30 +70,18 @@ export default function ApiTest({ getService }: FtrProviderContext) {
         (body) => !isFunctionTitleRequest(body)
       );
 
-      const responsePromise = new Promise<Response>((resolve, reject) => {
-        supertest
-          .post(PUBLIC_COMPLETE_API_URL)
-          .query({
-            format,
-          })
-          .set('kbn-xsrf', 'foo')
-          .set('elastic-api-version', '2023-10-31')
-          .send({
+      const responsePromise = observabilityAIAssistantAPIClient.adminUser({
+        endpoint: 'POST /api/observability_ai_assistant/chat/complete 2023-10-31',
+        params: {
+          query: { format },
+          body: {
             messages,
             connectorId,
             persist: true,
             actions,
             instructions,
-          })
-          .end((err, response) => {
-            if (err) {
-              return reject(err);
-            }
-            if (response.status !== 200) {
-              return reject(new Error(`${response.status}: ${JSON.stringify(response.body)}`));
-            }
-            return resolve(response);
-          });
+          },
+        },
       });
 
       const [conversationSimulator, titleSimulator] = await Promise.race([
@@ -141,32 +134,11 @@ export default function ApiTest({ getService }: FtrProviderContext) {
 
     before(async () => {
       proxy = await createLlmProxy(log);
-
-      const response = await supertest
-        .post('/api/actions/connector')
-        .set('kbn-xsrf', 'foo')
-        .send({
-          name: 'OpenAI Proxy',
-          connector_type_id: '.gen-ai',
-          config: {
-            apiProvider: 'OpenAI',
-            apiUrl: `http://localhost:${proxy.getPort()}`,
-          },
-          secrets: {
-            apiKey: 'my-api-key',
-          },
-        })
-        .expect(200);
-
-      connectorId = response.body.id;
+      connectorId = await createProxyActionConnector({ supertest, log, port: proxy.getPort() });
     });
 
     after(async () => {
-      await supertest
-        .delete(`/api/actions/connector/${connectorId}`)
-        .set('kbn-xsrf', 'foo')
-        .expect(204);
-
+      await deleteActionConnector({ supertest, connectorId, log });
       proxy.close();
     });
 
@@ -225,12 +197,17 @@ export default function ApiTest({ getService }: FtrProviderContext) {
     });
 
     describe('after adding an instruction', async () => {
-      let body: string;
+      let body: OpenAI.Chat.ChatCompletionCreateParamsNonStreaming;
 
       before(async () => {
         await getEvents(
           {
-            instructions: ['This is a random instruction'],
+            instructions: [
+              {
+                text: 'This is a random instruction',
+                instruction_type: 'user_instruction',
+              },
+            ],
           },
           async (conversationSimulator) => {
             body = conversationSimulator.body;
@@ -244,9 +221,7 @@ export default function ApiTest({ getService }: FtrProviderContext) {
       });
 
       it('includes the instruction in the system message', async () => {
-        const request = JSON.parse(body) as OpenAI.ChatCompletionCreateParams;
-
-        expect(request.messages[0].content).to.contain('This is a random instruction');
+        expect(body.messages[0].content).to.contain('This is a random instruction');
       });
     });
 
@@ -317,8 +292,3 @@ export default function ApiTest({ getService }: FtrProviderContext) {
     });
   });
 }
-
-function isFunctionTitleRequest(body: string) {
-  const parsedBody = JSON.parse(body) as OpenAI.Chat.ChatCompletionCreateParamsNonStreaming;
-  return parsedBody.tools?.find((fn) => fn.function.name === 'title_conversation') !== undefined;
-}
diff --git a/x-pack/test/observability_ai_assistant_functional/tests/contextual_insights/index.spec.ts b/x-pack/test/observability_ai_assistant_functional/tests/contextual_insights/index.spec.ts
index 7355b508ce5a0..b49c9fca76cd3 100644
--- a/x-pack/test/observability_ai_assistant_functional/tests/contextual_insights/index.spec.ts
+++ b/x-pack/test/observability_ai_assistant_functional/tests/contextual_insights/index.spec.ts
@@ -8,7 +8,6 @@
 import { apm, timerange } from '@kbn/apm-synthtrace-client';
 import expect from '@kbn/expect';
 import moment from 'moment';
-import OpenAI from 'openai';
 import {
   createLlmProxy,
   LlmProxy,
@@ -123,11 +122,9 @@ export default function ApiTest({ getService, getPageObjects }: FtrProviderConte
       it('should show the contextual insight component on the APM error details page', async () => {
         await navigateToError();
 
-        const interceptor = proxy.intercept(
-          'conversation',
-          (body) => !isFunctionTitleRequest(body),
-          'This error is nothing to worry about. Have a nice day!'
-        );
+        const interceptor = proxy.interceptConversation({
+          response: 'This error is nothing to worry about. Have a nice day!',
+        });
 
         await openContextualInsights();
 
@@ -141,8 +138,3 @@ export default function ApiTest({ getService, getPageObjects }: FtrProviderConte
     });
   });
 }
-
-function isFunctionTitleRequest(body: string) {
-  const parsedBody = JSON.parse(body) as OpenAI.Chat.ChatCompletionCreateParamsNonStreaming;
-  return parsedBody.functions?.find((fn) => fn.name === 'title_conversation') !== undefined;
-}
diff --git a/x-pack/test/observability_ai_assistant_functional/tests/conversations/index.spec.ts b/x-pack/test/observability_ai_assistant_functional/tests/conversations/index.spec.ts
index 3e766877c5bca..ff20297efdeca 100644
--- a/x-pack/test/observability_ai_assistant_functional/tests/conversations/index.spec.ts
+++ b/x-pack/test/observability_ai_assistant_functional/tests/conversations/index.spec.ts
@@ -9,9 +9,9 @@ import expect from '@kbn/expect';
 import { MessageRole } from '@kbn/observability-ai-assistant-plugin/common';
 import { ChatFeedback } from '@kbn/observability-ai-assistant-plugin/public/analytics/schemas/chat_feedback';
 import { pick } from 'lodash';
-import type OpenAI from 'openai';
 import {
   createLlmProxy,
+  isFunctionTitleRequest,
   LlmProxy,
 } from '../../../observability_ai_assistant_api_integration/common/create_llm_proxy';
 import { interceptRequest } from '../../common/intercept_request';
@@ -227,20 +227,15 @@ export default function ApiTest({ getService, getPageObjects }: FtrProviderConte
 
             describe('and sending over some text', () => {
               before(async () => {
-                const titleInterceptor = proxy.intercept(
-                  'title',
-                  (body) =>
-                    (
-                      JSON.parse(body) as OpenAI.Chat.ChatCompletionCreateParamsNonStreaming
-                    ).tools?.find((fn) => fn.function.name === 'title_conversation') !== undefined
+                const titleInterceptor = proxy.intercept('title', (body) =>
+                  isFunctionTitleRequest(body)
                 );
 
                 const conversationInterceptor = proxy.intercept(
                   'conversation',
                   (body) =>
-                    (
-                      JSON.parse(body) as OpenAI.Chat.ChatCompletionCreateParamsNonStreaming
-                    ).tools?.find((fn) => fn.function.name === 'title_conversation') === undefined
+                    body.tools?.find((fn) => fn.function.name === 'title_conversation') ===
+                    undefined
                 );
 
                 await testSubjects.setValue(ui.pages.conversations.chatInput, 'hello');