diff --git a/lib/web/assistant.go b/lib/web/assistant.go
index 32dc798e892ed..b5d66d2c432b6 100644
--- a/lib/web/assistant.go
+++ b/lib/web/assistant.go
@@ -375,9 +375,10 @@ func runAssistant(h *Handler, w http.ResponseWriter, r *http.Request,
 		closureReason := websocket.CloseNormalClosure
 		closureMsg := ""
 		if err != nil {
+			h.log.WithError(err).Error("Error in the Assistant loop")
 			_ = ws.WriteJSON(&assistantMessage{
 				Type:        assist.MessageKindError,
-				Payload:     err.Error(),
+				Payload:     "An error has occurred. Please try again later.",
 				CreatedTime: h.clock.Now().UTC().Format(time.RFC3339),
 			})
 			// Set server error code and message: https://datatracker.ietf.org/doc/html/rfc6455#section-7.4.1
diff --git a/web/packages/teleport/src/Assist/Conversation/Message.tsx b/web/packages/teleport/src/Assist/Conversation/Message.tsx
index 31f60bef5714e..4cb5f2fad5e18 100644
--- a/web/packages/teleport/src/Assist/Conversation/Message.tsx
+++ b/web/packages/teleport/src/Assist/Conversation/Message.tsx
@@ -107,6 +107,7 @@ function createComponentForEntry(
   switch (entry.type) {
     case ServerMessageType.Assist:
     case ServerMessageType.User:
+    case ServerMessageType.Error:
       return <MessageEntry content={entry.message} />;
 
     case ServerMessageType.Command:
diff --git a/web/packages/teleport/src/Assist/context/AssistContext.tsx b/web/packages/teleport/src/Assist/context/AssistContext.tsx
index 7ce6c0ed6136b..e76bd5f4d6a30 100644
--- a/web/packages/teleport/src/Assist/context/AssistContext.tsx
+++ b/web/packages/teleport/src/Assist/context/AssistContext.tsx
@@ -105,7 +105,7 @@ export function AssistContextProvider(props: PropsWithChildren<unknown>) {
     });
   }
 
-  function setupWebSocket(conversationId: string) {
+  function setupWebSocket(conversationId: string, initialMessage?: string) {
     activeWebSocket.current = new WebSocket(
       cfg.getAssistConversationWebSocketUrl(
         getHostName(),
@@ -123,6 +123,16 @@ export function AssistContextProvider(props: PropsWithChildren<unknown>) {
       TEN_MINUTES * 0.8
     );
 
+    activeWebSocket.current.onopen = () => {
+      if (initialMessage) {
+        activeWebSocket.current.send(initialMessage);
+      }
+    };
+
+    activeWebSocket.current.onclose = () => {
+      dispatch({ type: AssistStateActionType.SetStreaming, streaming: false });
+    };
+
     activeWebSocket.current.onmessage = async event => {
       const data = JSON.parse(event.data) as ServerMessage;
 
@@ -178,6 +188,21 @@ export function AssistContextProvider(props: PropsWithChildren<unknown>) {
 
           break;
         }
+
+        case ServerMessageType.Error:
+          dispatch({
+            type: AssistStateActionType.AddMessage,
+            messageType: ServerMessageType.Error,
+            message: data.payload,
+            conversationId,
+          });
+
+          dispatch({
+            type: AssistStateActionType.SetStreaming,
+            streaming: false,
+          });
+
+          break;
       }
     };
   }
@@ -273,7 +298,16 @@ export function AssistContextProvider(props: PropsWithChildren<unknown>) {
 
     dispatch({ type: AssistStateActionType.SetStreaming, streaming: true });
 
-    activeWebSocket.current.send(JSON.stringify({ payload: message }));
+    const data = JSON.stringify({ payload: message });
+
+    if (
+      !activeWebSocket.current ||
+      activeWebSocket.current.readyState === WebSocket.CLOSED
+    ) {
+      setupWebSocket(state.conversations.selectedId, data);
+    } else {
+      activeWebSocket.current.send(data);
+    }
 
     dispatch({
       type: AssistStateActionType.AddMessage,
diff --git a/web/packages/teleport/src/Assist/context/state.ts b/web/packages/teleport/src/Assist/context/state.ts
index c72222db77878..41dc5312ff367 100644
--- a/web/packages/teleport/src/Assist/context/state.ts
+++ b/web/packages/teleport/src/Assist/context/state.ts
@@ -90,7 +90,10 @@ export interface SetConversationMessagesAction {
 
 export interface AddMessageAction {
   type: AssistStateActionType.AddMessage;
-  messageType: ServerMessageType.User | ServerMessageType.Assist;
+  messageType:
+    | ServerMessageType.User
+    | ServerMessageType.Assist
+    | ServerMessageType.Error;
   message: string;
   conversationId: string;
 }
diff --git a/web/packages/teleport/src/Assist/context/utils.ts b/web/packages/teleport/src/Assist/context/utils.ts
index 08f41ebdd4fd4..e7473f7003ea7 100644
--- a/web/packages/teleport/src/Assist/context/utils.ts
+++ b/web/packages/teleport/src/Assist/context/utils.ts
@@ -32,6 +32,7 @@ function getMessageTypeAuthor(type: string) {
     case ServerMessageType.Command:
     case ServerMessageType.CommandResult:
     case ServerMessageType.CommandResultStream:
+    case ServerMessageType.Error:
       return Author.Teleport;
   }
 }
diff --git a/web/packages/teleport/src/Assist/types.ts b/web/packages/teleport/src/Assist/types.ts
index d9b2579c116b4..ba73068e0c80e 100644
--- a/web/packages/teleport/src/Assist/types.ts
+++ b/web/packages/teleport/src/Assist/types.ts
@@ -18,6 +18,7 @@ import { EventType } from 'teleport/lib/term/enums';
 export enum ServerMessageType {
   Assist = 'CHAT_MESSAGE_ASSISTANT',
   User = 'CHAT_MESSAGE_USER',
+  Error = 'CHAT_MESSAGE_ERROR',
   Command = 'COMMAND',
   CommandResult = 'COMMAND_RESULT',
   CommandResultStream = 'COMMAND_RESULT_STREAM',
@@ -85,6 +86,12 @@ export interface ResolvedUserServerMessage {
   created: Date;
 }
 
+export interface ResolvedErrorServerMessage {
+  type: ServerMessageType.Error;
+  message: string;
+  created: Date;
+}
+
 export interface ResolvedCommandResultStreamServerMessage {
   type: ServerMessageType.CommandResultStream;
   id: number;
@@ -99,6 +106,7 @@ export type ResolvedServerMessage =
   | ResolvedCommandServerMessage
   | ResolvedAssistServerMessage
   | ResolvedUserServerMessage
+  | ResolvedErrorServerMessage
   | ResolvedCommandResultServerMessage
   | ResolvedAssistThoughtServerMessage
   | ResolvedCommandResultStreamServerMessage;