diff --git a/x-pack/solutions/observability/plugins/observability_ai_assistant_app/public/rule_connector/ai_assistant.tsx b/x-pack/solutions/observability/plugins/observability_ai_assistant_app/public/rule_connector/ai_assistant.tsx
index ea3590740ab57..830380c9b949e 100644
--- a/x-pack/solutions/observability/plugins/observability_ai_assistant_app/public/rule_connector/ai_assistant.tsx
+++ b/x-pack/solutions/observability/plugins/observability_ai_assistant_app/public/rule_connector/ai_assistant.tsx
@@ -6,6 +6,7 @@
  */
 
 import React, { lazy } from 'react';
+import { isEmpty } from 'lodash';
 import type {
   ActionTypeModel as ConnectorTypeModel,
   GenericValidationResult,
@@ -19,6 +20,7 @@ import {
   CONNECTOR_REQUIRED,
   CONNECTOR_TITLE,
   MESSAGE_REQUIRED,
+  STATUS_REQUIRED,
 } from './translations';
 
 export function getConnectorType(
@@ -35,23 +37,26 @@ export function getConnectorType(
     validateParams: async (
       actionParams: ObsAIAssistantActionParams
     ): Promise<GenericValidationResult<ObsAIAssistantActionParams>> => {
-      const validationResult = {
-        errors: {
-          connector: [] as string[],
-          message: [] as string[],
-          prompts: [] as string[],
-        },
-      };
+      const validatePrompt = (prompt: { message: string; statuses: string[] }): string[] => {
+        const errors: string[] = [];
 
-      if (!actionParams.connector) {
-        validationResult.errors.connector.push(CONNECTOR_REQUIRED);
-      }
+        if (!prompt.message) {
+          errors.push(MESSAGE_REQUIRED);
+        }
+        if (isEmpty(prompt.statuses)) {
+          errors.push(STATUS_REQUIRED);
+        }
 
-      if (!actionParams.message) {
-        validationResult.errors.message.push(MESSAGE_REQUIRED);
-      }
+        return errors;
+      };
 
-      return validationResult;
+      return {
+        errors: {
+          connector: actionParams.connector ? [] : [CONNECTOR_REQUIRED],
+          message: actionParams.message && !actionParams.prompts ? [MESSAGE_REQUIRED] : [],
+          prompts: actionParams.prompts?.map(validatePrompt) || [],
+        },
+      };
     },
     actionParamsFields: lazy(() =>
       import('./ai_assistant_params').then(({ default: ActionParamsFields }) => ({
diff --git a/x-pack/solutions/observability/plugins/observability_ai_assistant_app/public/rule_connector/ai_assistant_params.tsx b/x-pack/solutions/observability/plugins/observability_ai_assistant_app/public/rule_connector/ai_assistant_params.tsx
index 08faf2166a6e5..a16baeadc5666 100644
--- a/x-pack/solutions/observability/plugins/observability_ai_assistant_app/public/rule_connector/ai_assistant_params.tsx
+++ b/x-pack/solutions/observability/plugins/observability_ai_assistant_app/public/rule_connector/ai_assistant_params.tsx
@@ -8,12 +8,25 @@
 import React, { useEffect } from 'react';
 import type { ActionParamsProps } from '@kbn/triggers-actions-ui-plugin/public';
 import { i18n } from '@kbn/i18n';
-import { EuiFormRow, EuiFlexItem, EuiSelect, EuiSpacer, EuiTextArea } from '@elastic/eui';
+import { FormattedMessage } from '@kbn/i18n-react';
+import {
+  EuiFormRow,
+  EuiFlexItem,
+  EuiSelect,
+  EuiSpacer,
+  EuiTextArea,
+  EuiComboBox,
+  EuiButton,
+  EuiFlexGroup,
+} from '@elastic/eui';
 import {
   ObservabilityAIAssistantService,
   useGenAIConnectorsWithoutContext,
 } from '@kbn/observability-ai-assistant-plugin/public';
+import { RuleFormParamsErrors } from '@kbn/alerts-ui-shared';
 import { ObsAIAssistantActionParams } from './types';
+import { ALERT_STATUSES } from '../../common/constants';
+import { MESSAGE_REQUIRED, STATUS_REQUIRED } from './translations';
 
 const ObsAIAssistantParamsFields: React.FunctionComponent<
   ActionParamsProps<ObsAIAssistantActionParams> & { service: ObservabilityAIAssistantService }
@@ -22,9 +35,65 @@ const ObsAIAssistantParamsFields: React.FunctionComponent<
     useGenAIConnectorsWithoutContext(service);
 
   useEffect(() => {
-    editAction('connector', selectedConnector, index);
+    if (selectedConnector !== actionParams.connector) {
+      editAction('connector', selectedConnector, index);
+    }
     // eslint-disable-next-line react-hooks/exhaustive-deps
-  }, [selectedConnector, index]);
+  }, [actionParams, selectedConnector, index]);
+
+  useEffect(() => {
+    // Ensure backwards compatibility by using the message field as a prompt if prompts are missing
+    if (!actionParams.prompts) {
+      editAction(
+        'prompts',
+        [
+          {
+            statuses: ALERT_STATUSES,
+            message: actionParams.message || '',
+          },
+        ],
+        index
+      );
+    }
+    // forward-compatible fallback.
+    if (actionParams.prompts && actionParams.prompts[0].message !== actionParams.message) {
+      editAction('message', actionParams.prompts[0].message, index);
+    }
+  }, [actionParams, editAction, index]);
+
+  const handleOnChange = (
+    key: 'statuses' | 'message',
+    value: string | string[],
+    promptIndex: number
+  ) => {
+    const prompts = actionParams.prompts ? [...actionParams.prompts] : [];
+    prompts[promptIndex] = { ...prompts[promptIndex], [key]: value };
+    editAction('prompts', prompts, index);
+  };
+
+  const handleAddPrompt = () => {
+    if (actionParams.prompts) {
+      const prompts = [
+        ...actionParams.prompts,
+        {
+          statuses: ALERT_STATUSES,
+          message: '',
+        },
+      ];
+      editAction('prompts', prompts, index);
+    }
+  };
+  const handleRemovePrompt = () => {
+    if (actionParams.prompts) {
+      const prompts = actionParams.prompts.slice(0, -1);
+      editAction('prompts', prompts, index);
+    }
+  };
+
+  const isValidField = (statusError: string, promptIndex: number) => {
+    const errorsList = ((errors.prompts as RuleFormParamsErrors)?.[promptIndex] as string[]) || [];
+    return errorsList.includes(statusError);
+  };
 
   return (
     <>
@@ -47,34 +116,99 @@ const ObsAIAssistantParamsFields: React.FunctionComponent<
             selectConnector(event.target.value);
             editAction('connector', event.target.value, index);
           }}
-          value={selectedConnector}
+          value={actionParams.connector}
         />
       </EuiFormRow>
 
+      {actionParams?.prompts?.map((prompt, promptIndex) => (
+        <div key={promptIndex}>
+          <EuiSpacer size="m" />
+          <EuiFormRow
+            fullWidth
+            label={i18n.translate(
+              'xpack.observabilityAiAssistant.alertConnector.messageTextAreaFieldLabel',
+              {
+                defaultMessage: 'On status changes',
+              }
+            )}
+          >
+            <EuiComboBox
+              fullWidth
+              id={`addNewActionConnectorActionGroup-${index}`}
+              data-test-subj={`addNewActionConnectorActionGroup-${index}`}
+              options={ALERT_STATUSES.map((id) => ({
+                label: id,
+              }))}
+              selectedOptions={prompt.statuses.map((id) => ({ label: id }))}
+              onChange={(statuses) => {
+                handleOnChange(
+                  'statuses',
+                  statuses.map((status) => status.label),
+                  promptIndex
+                );
+              }}
+              isClearable={true}
+              isInvalid={isValidField(STATUS_REQUIRED, promptIndex)}
+            />
+          </EuiFormRow>
+          <EuiSpacer size="m" />
+          <EuiFormRow
+            fullWidth
+            label={i18n.translate(
+              'xpack.observabilityAiAssistant.alertConnector.messageTextAreaFieldLabel',
+              {
+                defaultMessage: 'Message',
+              }
+            )}
+          >
+            <EuiFlexItem grow={false}>
+              <EuiTextArea
+                fullWidth
+                data-test-subj="observabilityAiAssistantAlertConnectorMessageTextArea"
+                value={prompt.message}
+                onChange={(event) => {
+                  handleOnChange('message', event.target.value, promptIndex);
+                }}
+                isInvalid={isValidField(MESSAGE_REQUIRED, promptIndex)}
+              />
+            </EuiFlexItem>
+          </EuiFormRow>
+        </div>
+      ))}
       <EuiSpacer size="m" />
-
-      <EuiFormRow
-        fullWidth
-        label={i18n.translate(
-          'xpack.observabilityAiAssistant.alertConnector.messageTextAreaFieldLabel',
-          {
-            defaultMessage: 'Message',
-          }
-        )}
-      >
-        <EuiFlexItem grow={false}>
-          <EuiTextArea
+      <EuiFlexGroup>
+        <EuiFlexItem grow>
+          <EuiButton
+            disabled={actionParams?.prompts?.length === 1}
+            size="m"
             fullWidth
-            data-test-subj="observabilityAiAssistantAlertConnectorMessageTextArea"
-            value={actionParams.message}
-            onChange={(event) => {
-              editAction('message', event.target.value, index);
-            }}
-            // @ts-expect-error upgrade typescript v5.1.6
-            isInvalid={errors.message?.length > 0}
-          />
+            color="danger"
+            iconType="minusInCircle"
+            data-test-subj="removePropmptButton"
+            onClick={handleRemovePrompt}
+          >
+            <FormattedMessage
+              id="xpack.observabilityAiAssistant.alertConnector.removePromptButtonLabel"
+              defaultMessage="Remove Prompt"
+            />
+          </EuiButton>
         </EuiFlexItem>
-      </EuiFormRow>
+        <EuiFlexItem grow>
+          <EuiButton
+            disabled={actionParams?.prompts?.length === ALERT_STATUSES.length}
+            size="m"
+            fullWidth
+            iconType="plusInCircle"
+            data-test-subj="addPrompButton"
+            onClick={handleAddPrompt}
+          >
+            <FormattedMessage
+              id="xpack.observabilityAiAssistant.alertConnector.addPromptButtonLabel"
+              defaultMessage="Add Prompt"
+            />
+          </EuiButton>
+        </EuiFlexItem>
+      </EuiFlexGroup>
     </>
   );
 };
diff --git a/x-pack/solutions/observability/plugins/observability_ai_assistant_app/public/rule_connector/translations.ts b/x-pack/solutions/observability/plugins/observability_ai_assistant_app/public/rule_connector/translations.ts
index 2dde4cd5e92db..5b2a8aa732130 100644
--- a/x-pack/solutions/observability/plugins/observability_ai_assistant_app/public/rule_connector/translations.ts
+++ b/x-pack/solutions/observability/plugins/observability_ai_assistant_app/public/rule_connector/translations.ts
@@ -34,3 +34,10 @@ export const MESSAGE_REQUIRED = i18n.translate(
     defaultMessage: 'Message is required.',
   }
 );
+
+export const STATUS_REQUIRED = i18n.translate(
+  'xpack.observabilityAiAssistant.requiredStatusField',
+  {
+    defaultMessage: 'Status is required.',
+  }
+);
diff --git a/x-pack/solutions/observability/plugins/observability_ai_assistant_app/tsconfig.json b/x-pack/solutions/observability/plugins/observability_ai_assistant_app/tsconfig.json
index fabeb14f8512b..145005f900fa1 100644
--- a/x-pack/solutions/observability/plugins/observability_ai_assistant_app/tsconfig.json
+++ b/x-pack/solutions/observability/plugins/observability_ai_assistant_app/tsconfig.json
@@ -84,7 +84,9 @@
     "@kbn/ai-assistant-icon",
     "@kbn/product-doc-base-plugin",
     "@kbn/rule-data-utils",
+    "@kbn/i18n-react",
     "@kbn/utility-types",
+    "@kbn/alerts-ui-shared"
   ],
   "exclude": ["target/**/*"]
 }