diff --git a/x-pack/platform/plugins/shared/observability_solution/observability_ai_assistant/public/components/insight/insight.tsx b/x-pack/platform/plugins/shared/observability_solution/observability_ai_assistant/public/components/insight/insight.tsx
index 680a92f559f0a..5be7a75449970 100644
--- a/x-pack/platform/plugins/shared/observability_solution/observability_ai_assistant/public/components/insight/insight.tsx
+++ b/x-pack/platform/plugins/shared/observability_solution/observability_ai_assistant/public/components/insight/insight.tsx
@@ -14,11 +14,13 @@ import {
   EuiText,
   EuiTextArea,
   EuiCallOut,
+  EuiLoadingSpinner,
 } from '@elastic/eui';
 import { i18n } from '@kbn/i18n';
 import { cloneDeep, isArray, isEmpty, last, once } from 'lodash';
 import React, { useCallback, useEffect, useMemo, useRef, useState } from 'react';
 import useObservable from 'react-use/lib/useObservable';
+import dedent from 'dedent';
 import { ILicense } from '@kbn/licensing-plugin/public';
 import { MessageRole, type Message } from '../../../common/types';
 import { ObservabilityAIAssistantChatServiceContext } from '../../context/observability_ai_assistant_chat_service_context';
@@ -41,6 +43,10 @@ import { InsightBase } from './insight_base';
 import { ActionsMenu } from './actions_menu';
 import { ObservabilityAIAssistantTelemetryEventType } from '../../analytics/telemetry_event_type';
 
+// defined and used in x-pack/solutions/observability/plugins/observability/public/pages/alert_details/alert_details_contextual_insights.tsx
+const CONTEXT_INSTRUCTION =
+  'The following contextual information is available to help you understand the alert';
+
 function getLastMessageOfType(messages: Message[], role: MessageRole) {
   return last(messages.filter((msg) => msg.message.role === role));
 }
@@ -288,16 +294,61 @@ export function Insight({
     [service]
   );
 
+  const getPromptToEdit = () => {
+    const clonedMessages = cloneDeep(messages.messages);
+    const lastUserPrompt = getLastMessageOfType(clonedMessages, MessageRole.User)?.message.content;
+
+    if (!lastUserPrompt) {
+      return '';
+    }
+
+    try {
+      const { instructions = '' } = JSON.parse(lastUserPrompt);
+
+      // instructions is a large multiline string with contextual information appended to it.
+      // We'll split at CONTEXT_INSTRUCTION so that we can extract the instructions the user needs to edit
+      const [beforeContextInstruction] = instructions.split(CONTEXT_INSTRUCTION);
+      return beforeContextInstruction.trim();
+    } catch (e) {
+      return '';
+    }
+  };
+
   const onEditPrompt = (newPrompt: string) => {
     const clonedMessages = cloneDeep(messages.messages);
     const userMessage = getLastMessageOfType(clonedMessages, MessageRole.User);
     if (!userMessage) return false;
 
-    userMessage.message.content = newPrompt;
-    setIsPromptUpdated(true);
-    setMessages({ messages: clonedMessages, status: FETCH_STATUS.SUCCESS });
-    setEditingPrompt(false);
-    return true;
+    try {
+      const parsedContent = JSON.parse(userMessage.message.content || '');
+
+      if (!parsedContent.instructions) {
+        return false;
+      }
+
+      const [_beforeContextInstruction, afterContextInstruction] =
+        parsedContent.instructions.split(CONTEXT_INSTRUCTION);
+
+      // Rebuild instructions with the new prompt, preserving everything after the delimiter
+      const updatedInstructions = dedent(
+        `${newPrompt}
+      ${CONTEXT_INSTRUCTION}
+      ${afterContextInstruction}`
+      );
+
+      // Assign the updated instructions
+      parsedContent.instructions = updatedInstructions;
+      userMessage.message.content = JSON.stringify(parsedContent);
+
+      setIsPromptUpdated(true);
+      setMessages({ messages: clonedMessages, status: FETCH_STATUS.SUCCESS });
+      setEditingPrompt(false);
+      return true;
+    } catch (e) {
+      // eslint-disable-next-line no-console
+      console.error('Failed to edit prompt:', e);
+      return false;
+    }
   };
 
   const handleCancel = () => {
@@ -372,15 +423,19 @@ export function Insight({
       </>
     );
   } else if (isEditingPrompt) {
-    children = (
-      <PromptEdit
-        initialPrompt={
-          getLastMessageOfType(messages.messages, MessageRole.User)?.message.content || ''
-        }
-        onSend={onEditPrompt}
-        onCancel={handleCancel}
-      />
-    );
+    const instructionToEdit = getPromptToEdit();
+
+    if (messages.status === FETCH_STATUS.SUCCESS && instructionToEdit) {
+      children = (
+        <PromptEdit
+          initialPrompt={instructionToEdit}
+          onSend={onEditPrompt}
+          onCancel={handleCancel}
+        />
+      );
+    } else {
+      children = <EuiLoadingSpinner size="m" />;
+    }
   } else if (!connectors.loading && !connectors.connectors?.length) {
     children = (
       <MissingCredentialsCallout connectorsManagementHref={getConnectorsManagementHref(http!)} />
diff --git a/x-pack/solutions/observability/plugins/observability/public/pages/alert_details/alert_details_contextual_insights.tsx b/x-pack/solutions/observability/plugins/observability/public/pages/alert_details/alert_details_contextual_insights.tsx
index 17f7d335624d1..d63fd5d06eccd 100644
--- a/x-pack/solutions/observability/plugins/observability/public/pages/alert_details/alert_details_contextual_insights.tsx
+++ b/x-pack/solutions/observability/plugins/observability/public/pages/alert_details/alert_details_contextual_insights.tsx
@@ -13,6 +13,10 @@ import { type AlertDetailsContextualInsight } from '../../../server/services';
 import { useKibana } from '../../utils/kibana_react';
 import { AlertData } from '../../hooks/use_fetch_alert_detail';
 
+// used in x-pack/platform/plugins/shared/observability_solution/observability_ai_assistant/public/components/insight/insight.tsx
+const CONTEXT_INSTRUCTION =
+  'The following contextual information is available to help you understand the alert';
+
 export function AlertDetailContextualInsights({ alert }: { alert: AlertData | null }) {
   const {
     services: { observabilityAIAssistant, http },
@@ -62,7 +66,7 @@ export function AlertDetailContextualInsights({ alert }: { alert: AlertData | nu
         instructions: dedent(
           `I'm an SRE. I am looking at an alert that was triggered. I want to understand why it was triggered, what it means, and what I should do next.
 
-        The following contextual information is available to help you understand the alert:
+        ${CONTEXT_INSTRUCTION}:
         ${obsAlertContext}
 
         The user already know the alert reason so do not repeat this: ${alert.formatted.reason}