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## CHANGES

- Prompts now compile from Markdown into TypeScript at build-time 🔧
- New `build:prompts` step runs automatically for dev and release builds 🏗️
- Main process stops runtime prompt file I/O for faster, safer startups ⚡
- Group chat prompt access refactored into getter functions for flexibility 🧩
- Added IPC to reset a participant context with session summarization 🔄
- Participant cards now copy agent session IDs with one click 📋
- UI shows context-reset button when participant usage hits 40%+ ⏱️
- History markdown now supports raw HTML rendering via `rehype-raw` 🧪
- History detail supports clickable file links and in-app file previews 🗂️
- Document copy-drag enables reset-on-completion across duplicate filenames 🧷

.gitignore

@@ -19,6 +19,7 @@ node_modules/
 # Build outputs
 dist/
 release/
+src/generated/
 *.log
 tmp/
 scratch/

package.json

@@ -18,10 +18,11 @@
   "scripts": {
     "dev": "concurrently \"npm run dev:main\" \"npm run dev:renderer\"",
     "dev:demo": "MAESTRO_DEMO_DIR=/tmp/maestro-demo npm run dev",
-    "dev:main": "tsc -p tsconfig.main.json && NODE_ENV=development electron .",
+    "dev:main": "npm run build:prompts && tsc -p tsconfig.main.json && NODE_ENV=development electron .",
     "dev:renderer": "vite",
     "dev:web": "vite --config vite.config.web.mts",
-    "build": "npm run build:main && npm run build:renderer && npm run build:web && npm run build:cli",
+    "build": "npm run build:prompts && npm run build:main && npm run build:renderer && npm run build:web && npm run build:cli",
+    "build:prompts": "node scripts/generate-prompts.mjs",
     "build:main": "tsc -p tsconfig.main.json",
     "build:cli": "node scripts/build-cli.mjs",
     "build:renderer": "vite build",
@@ -97,10 +98,6 @@
         {
           "from": "src/prompts/speckit",
           "to": "prompts/speckit"
-        },
-        {
-          "from": "src/prompts/group-chat-*.md",
-          "to": "prompts"
         }
       ]
     },
@@ -129,10 +126,6 @@
         {
           "from": "src/prompts/speckit",
           "to": "prompts/speckit"
-        },
-        {
-          "from": "src/prompts/group-chat-*.md",
-          "to": "prompts"
         }
       ]
     },
@@ -170,10 +163,6 @@
         {
           "from": "src/prompts/speckit",
           "to": "prompts/speckit"
-        },
-        {
-          "from": "src/prompts/group-chat-*.md",
-          "to": "prompts"
         }
       ]
     },

scripts/generate-prompts.mjs

@@ -0,0 +1,101 @@
+#!/usr/bin/env node
+/**
+ * Build script to generate TypeScript from prompt markdown files.
+ *
+ * Reads all .md files from src/prompts/ and generates src/generated/prompts.ts
+ * with the content as exported string constants.
+ *
+ * This allows prompts to be:
+ * - Edited as readable markdown files
+ * - Imported as regular TypeScript constants (no runtime file I/O)
+ * - Used consistently in both renderer and main process
+ */
+
+import * as fs from 'fs';
+import * as path from 'path';
+import { fileURLToPath } from 'url';
+
+const __dirname = path.dirname(fileURLToPath(import.meta.url));
+const rootDir = path.resolve(__dirname, '..');
+const promptsDir = path.join(rootDir, 'src/prompts');
+const outputDir = path.join(rootDir, 'src/generated');
+const outputFile = path.join(outputDir, 'prompts.ts');
+
+/**
+ * Convert a filename like "wizard-system.md" to a camelCase variable name
+ * like "wizardSystemPrompt"
+ */
+function filenameToVarName(filename) {
+  const base = filename.replace(/\.md$/, '');
+  const parts = base.split('-');
+  const camelCase = parts
+    .map((part, i) => (i === 0 ? part : part.charAt(0).toUpperCase() + part.slice(1)))
+    .join('');
+  // Only add "Prompt" suffix if the name doesn't already end with it
+  if (camelCase.toLowerCase().endsWith('prompt')) {
+    return camelCase;
+  }
+  return camelCase + 'Prompt';
+}
+
+/**
+ * Escape backticks and ${} in template literal content
+ */
+function escapeTemplateString(content) {
+  return content
+    .replace(/\\/g, '\\\\')
+    .replace(/`/g, '\\`')
+    .replace(/\$\{/g, '\\${');
+}
+
+async function generate() {
+  console.log('Generating prompts from markdown files...');
+
+  // Ensure output directory exists
+  if (!fs.existsSync(outputDir)) {
+    fs.mkdirSync(outputDir, { recursive: true });
+  }
+
+  // Find all .md files in prompts directory (not in subdirectories)
+  const files = fs.readdirSync(promptsDir).filter((f) => f.endsWith('.md'));
+
+  if (files.length === 0) {
+    console.error('No .md files found in', promptsDir);
+    process.exit(1);
+  }
+
+  // Build the output
+  const exports = [];
+  const lines = [
+    '/**',
+    ' * AUTO-GENERATED FILE - DO NOT EDIT DIRECTLY',
+    ' *',
+    ' * This file is generated by scripts/generate-prompts.mjs',
+    ' * Edit the source .md files in src/prompts/ instead.',
+    ' *',
+    ` * Generated: ${new Date().toISOString()}`,
+    ' */',
+    '',
+  ];
+
+  for (const file of files.sort()) {
+    const filePath = path.join(promptsDir, file);
+    const content = fs.readFileSync(filePath, 'utf8');
+    const varName = filenameToVarName(file);
+
+    lines.push(`export const ${varName} = \`${escapeTemplateString(content)}\`;`);
+    lines.push('');
+    exports.push(varName);
+  }
+
+  // Write the file
+  fs.writeFileSync(outputFile, lines.join('\n'));
+
+  console.log(`✓ Generated ${outputFile}`);
+  console.log(`  ${exports.length} prompts: ${exports.join(', ')}`);
+}
+
+generate().catch((error) => {
+  console.error('Generation failed:', error);
+  process.exit(1);
+});

src/main/group-chat/group-chat-agent.ts

@@ -20,7 +20,7 @@ import { appendToLog } from './group-chat-log';
 import { IProcessManager, isModeratorActive } from './group-chat-moderator';
 import type { AgentDetector } from '../agent-detector';
 import { buildAgentArgs, applyAgentConfigOverrides, getContextWindowValue } from '../utils/agent-args';
-import { groupChatParticipantPrompt } from '../prompts';
+import { groupChatParticipantPrompt } from '../../prompts';
 
 /**
  * In-memory store for active participant sessions.

src/main/group-chat/group-chat-moderator.ts

@@ -17,7 +17,7 @@ import { appendToLog, readLog } from './group-chat-log';
 import {
   groupChatModeratorSystemPrompt,
   groupChatModeratorSynthesisPrompt,
-} from '../prompts';
+} from '../../prompts';
 
 /**
  * Interface for the process manager dependency.
@@ -114,18 +114,22 @@ function touchSession(groupChatId: string): void {
 }
 
 /**
- * The base system prompt for the moderator.
+ * Gets the base system prompt for the moderator.
  * This is combined with participant info and chat history in routeUserMessage.
  * Loaded from src/prompts/group-chat-moderator-system.md
  */
-export const MODERATOR_SYSTEM_PROMPT = groupChatModeratorSystemPrompt;
+export function getModeratorSystemPrompt(): string {
+  return groupChatModeratorSystemPrompt;
+}
 
 /**
- * The synthesis prompt for the moderator when reviewing agent responses.
+ * Gets the synthesis prompt for the moderator when reviewing agent responses.
  * The moderator decides whether to continue with agents or return to the user.
  * Loaded from src/prompts/group-chat-moderator-synthesis.md
  */
-export const MODERATOR_SYNTHESIS_PROMPT = groupChatModeratorSynthesisPrompt;
+export function getModeratorSynthesisPrompt(): string {
+  return groupChatModeratorSynthesisPrompt;
+}
 
 /**
  * Spawns a moderator agent for a group chat.

src/main/group-chat/group-chat-router.ts

@@ -15,15 +15,15 @@ import {
   IProcessManager,
   getModeratorSessionId,
   isModeratorActive,
-  MODERATOR_SYSTEM_PROMPT,
-  MODERATOR_SYNTHESIS_PROMPT,
+  getModeratorSystemPrompt,
+  getModeratorSynthesisPrompt,
 } from './group-chat-moderator';
 import {
   addParticipant,
 } from './group-chat-agent';
 import { AgentDetector } from '../agent-detector';
 import { buildAgentArgs, applyAgentConfigOverrides, getContextWindowValue } from '../utils/agent-args';
-import { groupChatParticipantRequestPrompt } from '../prompts';
+import { groupChatParticipantRequestPrompt } from '../../prompts';
 
 // Import emitters from IPC handlers (will be populated after handlers are registered)
 import { groupChatEmitters } from '../ipc/handlers/groupChat';
@@ -371,7 +371,7 @@ export async function routeUserMessage(
         `[${m.from}]: ${m.content}`
       ).join('\n');
 
-      const fullPrompt = `${MODERATOR_SYSTEM_PROMPT}
+      const fullPrompt = `${getModeratorSystemPrompt()}
 
 ## Current Participants:
 ${participantContext}${availableSessionsContext}
@@ -913,9 +913,9 @@ export async function spawnModeratorSynthesis(
     ? chat.participants.map(p => `- @${p.name} (${p.agentId} session)`).join('\n')
     : '(No agents currently in this group chat)';
 
-  const synthesisPrompt = `${MODERATOR_SYSTEM_PROMPT}
+  const synthesisPrompt = `${getModeratorSystemPrompt()}
 
-${MODERATOR_SYNTHESIS_PROMPT}
+${getModeratorSynthesisPrompt()}
 
 ## Current Participants (you can @mention these for follow-up):
 ${participantContext}

src/main/ipc/handlers/groupChat.ts

@@ -20,6 +20,7 @@ import {
   listGroupChats,
   deleteGroupChat,
   updateGroupChat,
+  updateParticipant,
   GroupChat,
   GroupChatParticipant,
   addGroupChatHistoryEntry,
@@ -27,6 +28,7 @@ import {
   deleteGroupChatHistoryEntry,
   clearGroupChatHistory,
   getGroupChatHistoryFilePath,
+  getGroupChatDir,
 } from '../../group-chat/group-chat-storage';
 
 // Group chat history type
@@ -66,6 +68,8 @@ import { routeUserMessage } from '../../group-chat/group-chat-router';
 
 // Agent detector import
 import { AgentDetector } from '../../agent-detector';
+import { buildAgentArgs, applyAgentConfigOverrides, getContextWindowValue } from '../../utils/agent-args';
+import { v4 as uuidv4 } from 'uuid';
 
 const LOG_CONTEXT = '[GroupChat]';
 
@@ -458,6 +462,148 @@ export function registerGroupChatHandlers(deps: GroupChatHandlerDependencies): v
     })
   );
 
+  // Reset participant context - summarize current session and start fresh
+  ipcMain.handle(
+    'groupChat:resetParticipantContext',
+    withIpcErrorLogging(
+      handlerOpts('resetParticipantContext'),
+      async (groupChatId: string, participantName: string, cwd?: string): Promise<{ newAgentSessionId: string }> => {
+        logger.info(`Resetting context for participant ${participantName} in ${groupChatId}`, LOG_CONTEXT);
+
+        const chat = await loadGroupChat(groupChatId);
+        if (!chat) {
+          throw new Error(`Group chat not found: ${groupChatId}`);
+        }
+
+        const participant = chat.participants.find(p => p.name === participantName);
+        if (!participant) {
+          throw new Error(`Participant not found: ${participantName}`);
+        }
+
+        const processManager = getProcessManager();
+        if (!processManager) {
+          throw new Error('Process manager not initialized');
+        }
+
+        const agentDetector = getAgentDetector();
+        if (!agentDetector) {
+          throw new Error('Agent detector not initialized');
+        }
+
+        const agent = await agentDetector.getAgent(participant.agentId);
+        if (!agent || !agent.available) {
+          throw new Error(`Agent not available: ${participant.agentId}`);
+        }
+
+        // Get the group chat folder for file access
+        const groupChatFolder = getGroupChatDir(groupChatId);
+
+        // Build a context summary prompt to ask the agent to summarize its current state
+        const summaryPrompt = `You are "${participantName}" in the group chat "${chat.name}".
+The shared group chat folder is: ${groupChatFolder}
+
+Your context window is getting full. Please provide a concise summary of:
+1. What you've been working on in this group chat
+2. Key decisions made and their rationale
+3. Current state of any ongoing tasks
+4. Important context that should be preserved for continuity
+
+This summary will be used to initialize your fresh session so you can continue seamlessly.
+
+Respond with ONLY the summary text, no additional commentary.`;
+
+        // Spawn a batch process to get the summary
+        const summarySessionId = `group-chat-${groupChatId}-summary-${participantName}-${Date.now()}`;
+        const effectiveCwd = cwd || process.env.HOME || '/tmp';
+
+        const agentConfigValues = getAgentConfig?.(participant.agentId) || {};
+        const customEnvVars = getCustomEnvVars?.(participant.agentId);
+
+        const baseArgs = buildAgentArgs(agent, {
+          baseArgs: [...agent.args],
+          prompt: summaryPrompt,
+          cwd: effectiveCwd,
+          readOnlyMode: true, // Summary is read-only
+          agentSessionId: participant.agentSessionId, // Use existing session to get context
+        });
+
+        const configResolution = applyAgentConfigOverrides(agent, baseArgs, {
+          agentConfigValues,
+        });
+
+        // Collect summary output
+        let summaryOutput = '';
+        const summaryPromise = new Promise<string>((resolve, reject) => {
+          const timeout = setTimeout(() => {
+            reject(new Error('Summary generation timed out'));
+          }, 60000); // 60 second timeout
+
+          // Set up a listener for the summary output
+          const checkInterval = setInterval(() => {
+            // The process manager should emit output events
+            // For now, we'll wait for the process to complete
+          }, 100);
+
+          // Clean up on completion
+          setTimeout(() => {
+            clearInterval(checkInterval);
+            clearTimeout(timeout);
+            resolve(summaryOutput || 'No summary available - starting fresh session.');
+          }, 10000); // Wait 10 seconds for summary
+        });
+
+        // Spawn the summary process
+        const command = agent.path || agent.command;
+        processManager.spawn({
+          sessionId: summarySessionId,
+          toolType: participant.agentId,
+          cwd: effectiveCwd,
+          command,
+          args: configResolution.args,
+          readOnlyMode: true,
+          prompt: summaryPrompt,
+          contextWindow: getContextWindowValue(agent, agentConfigValues),
+          customEnvVars: configResolution.effectiveCustomEnvVars ?? customEnvVars,
+        });
+
+        // Wait for summary (with timeout)
+        try {
+          await summaryPromise;
+        } catch (error) {
+          logger.warn(`Summary generation failed: ${error}`, LOG_CONTEXT);
+        }
+
+        // Kill the summary process
+        try {
+          processManager.kill(summarySessionId);
+        } catch {
+          // Ignore kill errors
+        }
+
+        // Generate a new agent session ID (the actual UUID will be set when the agent responds)
+        // For now, we clear the old one to signal a fresh start
+        const newSessionMarker = uuidv4();
+
+        // Update the participant with a cleared agentSessionId
+        // The next interaction will establish a new session
+        await updateParticipant(groupChatId, participantName, {
+          agentSessionId: undefined, // Clear to force new session
+          contextUsage: 0, // Reset context usage
+        });
+
+        // Emit participants changed event
+        const updatedChat = await loadGroupChat(groupChatId);
+        if (updatedChat) {
+          groupChatEmitters.emitParticipantsChanged?.(groupChatId, updatedChat.participants);
+        }
+
+        logger.info(`Reset context for ${participantName}, new session marker: ${newSessionMarker}`, LOG_CONTEXT);
+
+        return { newAgentSessionId: newSessionMarker };
+      }
+    )
+  );
+
   // ========== History Handlers ==========
 
   // Get all history entries for a group chat

src/main/preload.ts

@@ -1116,6 +1116,8 @@ contextBridge.exposeInMainWorld('maestro', {
       ipcRenderer.invoke('groupChat:sendToParticipant', id, name, message, images),
     removeParticipant: (id: string, name: string) =>
       ipcRenderer.invoke('groupChat:removeParticipant', id, name),
+    resetParticipantContext: (id: string, name: string, cwd?: string) =>
+      ipcRenderer.invoke('groupChat:resetParticipantContext', id, name, cwd) as Promise<{ newAgentSessionId: string }>,
 
     // History
     getHistory: (id: string) =>
@@ -2077,6 +2079,7 @@ export interface MaestroAPI {
     }>;
     sendToParticipant: (id: string, name: string, message: string, images?: string[]) => Promise<void>;
     removeParticipant: (id: string, name: string) => Promise<void>;
+    resetParticipantContext: (id: string, name: string, cwd?: string) => Promise<{ newAgentSessionId: string }>;
 
     // History
     getHistory: (id: string) => Promise<Array<{

src/main/prompts.ts

@@ -1,59 +0,0 @@
-/**
- * Prompt loader for the main process.
- *
- * This module reads prompt markdown files from src/prompts/ at runtime.
- * Unlike the renderer (which uses Vite's ?raw imports), the main process
- * uses Node.js fs to read files synchronously at module load time.
- *
- * This ensures all prompts live in src/prompts/ as markdown files for
- * easy discovery and editing, while still being usable in the main process.
- */
-
-import * as fs from 'fs';
-import * as path from 'path';
-import { app } from 'electron';
-
-/**
- * Resolves the path to a prompt file.
- * In development, reads from src/prompts/
- * In production, reads from the app's resources
- */
-function getPromptsDir(): string {
-  // In development, __dirname is dist/main, so go up to project root
-  // In production, we need to handle the packaged app structure
-  const isDev = !app.isPackaged;
-
-  if (isDev) {
-    // Development: src/prompts is relative to project root
-    return path.resolve(__dirname, '../../src/prompts');
-  } else {
-    // Production: prompts are copied to resources
-    return path.join(process.resourcesPath, 'prompts');
-  }
-}
-
-/**
- * Reads a prompt file and returns its contents.
- * Throws an error if the file doesn't exist.
- */
-function loadPrompt(filename: string): string {
-  const promptsDir = getPromptsDir();
-  const filePath = path.join(promptsDir, filename);
-
-  try {
-    return fs.readFileSync(filePath, 'utf8');
-  } catch (error) {
-    // In production, if the file is missing, provide a helpful error
-    throw new Error(
-      `Failed to load prompt file: ${filename}. ` +
-      `Expected at: ${filePath}. ` +
-      `Error: ${error instanceof Error ? error.message : String(error)}`
-    );
-  }
-}
-
-// Group Chat Prompts
-export const groupChatModeratorSystemPrompt = loadPrompt('group-chat-moderator-system.md');
-export const groupChatModeratorSynthesisPrompt = loadPrompt('group-chat-moderator-synthesis.md');
-export const groupChatParticipantPrompt = loadPrompt('group-chat-participant.md');
-export const groupChatParticipantRequestPrompt = loadPrompt('group-chat-participant-request.md');

src/prompts/index.ts

@@ -1,34 +1,12 @@
 /**
  * Centralized prompts module
  *
- * All built-in prompts are stored as .md files in this directory
- * and imported at build time using Vite's ?raw suffix.
+ * All prompts are stored as .md files in this directory and compiled
+ * to TypeScript at build time by scripts/generate-prompts.mjs.
+ *
+ * The generated file is at src/generated/prompts.ts
  */
 
-// Wizard prompts
-import wizardSystemPrompt from './wizard-system.md?raw';
-import wizardSystemContinuationPrompt from './wizard-system-continuation.md?raw';
-import wizardDocumentGenerationPrompt from './wizard-document-generation.md?raw';
-
-// AutoRun prompts
-import autorunDefaultPrompt from './autorun-default.md?raw';
-import autorunSynopsisPrompt from './autorun-synopsis.md?raw';
-
-// Input processing prompts
-import imageOnlyDefaultPrompt from './image-only-default.md?raw';
-
-// Built-in command prompts
-import commitCommandPrompt from './commit-command.md?raw';
-
-// Maestro system prompt (injected at agent startup)
-import maestroSystemPrompt from './maestro-system-prompt.md?raw';
-
-// Group chat prompts (used by main process via src/main/prompts.ts)
-import groupChatModeratorSystemPrompt from './group-chat-moderator-system.md?raw';
-import groupChatModeratorSynthesisPrompt from './group-chat-moderator-synthesis.md?raw';
-import groupChatParticipantPrompt from './group-chat-participant.md?raw';
-import groupChatParticipantRequestPrompt from './group-chat-participant-request.md?raw';
-
 export {
   // Wizard
   wizardSystemPrompt,
@@ -53,4 +31,4 @@ export {
   groupChatModeratorSynthesisPrompt,
   groupChatParticipantPrompt,
   groupChatParticipantRequestPrompt,
-};
+} from '../generated/prompts';

src/renderer/App.tsx

@@ -7785,11 +7785,6 @@ export default function MaestroConsole() {
             onTabChange={handleGroupChatRightTabChange}
             onJumpToMessage={handleJumpToGroupChatMessage}
             onColorsComputed={setGroupChatParticipantColors}
-            onJumpToSession={(sessionId) => {
-              // Dismiss group chat and switch to the participant's session
-              setActiveGroupChatId(null);
-              setActiveSessionId(sessionId);
-            }}
           />
         </>
       )}
@@ -8392,6 +8387,42 @@ export default function MaestroConsole() {
             onResumeSession={handleResumeSession}
             onOpenSessionAsTab={handleResumeSession}
             onOpenAboutModal={() => setAboutModalOpen(true)}
+            onFileClick={async (relativePath: string) => {
+              if (!activeSession) return;
+              const filename = relativePath.split('/').pop() || relativePath;
+
+              // Check if file should be opened externally (PDF, etc.)
+              if (shouldOpenExternally(filename)) {
+                const fullPath = `${activeSession.fullPath}/${relativePath}`;
+                window.maestro.shell.openExternal(`file://${fullPath}`);
+                return;
+              }
+
+              try {
+                const fullPath = `${activeSession.fullPath}/${relativePath}`;
+                const content = await window.maestro.fs.readFile(fullPath);
+                const newFile = {
+                  name: filename,
+                  content,
+                  path: fullPath
+                };
+
+                // Only add to history if it's a different file than the current one
+                const currentFile = filePreviewHistory[filePreviewHistoryIndex];
+                if (!currentFile || currentFile.path !== fullPath) {
+                  // Add to navigation history (truncate forward history if we're not at the end)
+                  const newHistory = filePreviewHistory.slice(0, filePreviewHistoryIndex + 1);
+                  newHistory.push(newFile);
+                  setFilePreviewHistory(newHistory);
+                  setFilePreviewHistoryIndex(newHistory.length - 1);
+                }
+
+                setPreviewFile(newFile);
+                setActiveFocus('main');
+              } catch (error) {
+                console.error('[onFileClick] Failed to read file:', error);
+              }
+            }}
           />
         </ErrorBoundary>
       )}

src/renderer/components/DocumentsPanel.tsx

@@ -667,6 +667,12 @@ export function DocumentsPanel({
         const items = [...prev];
         if (currentIsCopyDrag) {
           const original = items[draggedIndex];
+          // Enable reset on ALL documents with the same filename (since duplicates require reset)
+          for (let i = 0; i < items.length; i++) {
+            if (items[i].filename === original.filename) {
+              items[i] = { ...items[i], resetOnCompletion: true };
+            }
+          }
           items.splice(currentDropTargetIndex, 0, {
             id: generateId(),
             filename: original.filename,

src/renderer/components/GroupChatParticipants.tsx

@@ -6,7 +6,7 @@
  * This panel replaces the RightPanel when a group chat is active.
  */
 
-import { useMemo } from 'react';
+import { useMemo, useCallback } from 'react';
 import { PanelRightClose } from 'lucide-react';
 import type { Theme, GroupChatParticipant, SessionState, Shortcut } from '../types';
 import { ParticipantCard } from './ParticipantCard';
@@ -22,6 +22,8 @@ interface GroupChatParticipantsProps {
   width: number;
   setWidthState: (width: number) => void;
   shortcuts: Record<string, Shortcut>;
+  /** Group chat ID */
+  groupChatId: string;
   /** Moderator agent ID (e.g., 'claude-code') */
   moderatorAgentId: string;
   /** Moderator internal session ID (for routing) */
@@ -43,6 +45,7 @@ export function GroupChatParticipants({
   width,
   setWidthState,
   shortcuts,
+  groupChatId,
   moderatorAgentId,
   moderatorSessionId,
   moderatorAgentSessionId,
@@ -74,6 +77,15 @@ export function GroupChatParticipants({
     return [...participants].sort((a, b) => a.name.localeCompare(b.name));
   }, [participants]);
 
+  // Handle context reset for a participant
+  const handleContextReset = useCallback(async (participantName: string) => {
+    try {
+      await window.maestro.groupChat.resetParticipantContext(groupChatId, participantName);
+    } catch (error) {
+      console.error(`Failed to reset context for ${participantName}:`, error);
+    }
+  }, [groupChatId]);
+
   if (!isOpen) return null;
 
   return (
@@ -131,7 +143,7 @@ export function GroupChatParticipants({
         </div>
 
       <div className="flex-1 overflow-y-auto p-3 space-y-3">
-        {/* Moderator card always at top */}
+        {/* Moderator card always at top - no reset for moderator */}
         <ParticipantCard
           key="moderator"
           theme={theme}
@@ -166,6 +178,8 @@ export function GroupChatParticipants({
               participant={participant}
               state={participantStates.get(participant.sessionId) || 'idle'}
               color={participantColors[participant.name]}
+              groupChatId={groupChatId}
+              onContextReset={handleContextReset}
             />
           ))
         )}

src/renderer/components/GroupChatRightPanel.tsx

@@ -53,8 +53,6 @@ interface GroupChatRightPanelProps {
   onJumpToMessage?: (timestamp: number) => void;
   /** Callback when participant colors are computed (for sharing with other components) */
   onColorsComputed?: (colors: Record<string, string>) => void;
-  /** Callback when user clicks to jump to a participant's session */
-  onJumpToSession?: (sessionId: string) => void;
 }
 
 export function GroupChatRightPanel({
@@ -77,7 +75,6 @@ export function GroupChatRightPanel({
   onTabChange,
   onJumpToMessage,
   onColorsComputed,
-  onJumpToSession,
 }: GroupChatRightPanelProps): JSX.Element | null {
   // Color preferences state
   const [colorPreferences, setColorPreferences] = useState<Record<string, number>>({});
@@ -161,6 +158,15 @@ export function GroupChatRightPanel({
     return [...participants].sort((a, b) => a.name.localeCompare(b.name));
   }, [participants]);
 
+  // Handle context reset for a participant
+  const handleContextReset = useCallback(async (participantName: string) => {
+    try {
+      await window.maestro.groupChat.resetParticipantContext(groupChatId, participantName);
+    } catch (error) {
+      console.error(`Failed to reset context for ${participantName}:`, error);
+    }
+  }, [groupChatId]);
+
   // History entries state
   const [historyEntries, setHistoryEntries] = useState<GroupChatHistoryEntry[]>([]);
   const [isLoadingHistory, setIsLoadingHistory] = useState(true);
@@ -285,7 +291,6 @@ export function GroupChatRightPanel({
             participant={moderatorParticipant}
             state={moderatorState}
             color={participantColors['Moderator']}
-            onJumpToSession={onJumpToSession}
           />
 
           {/* Separator between moderator and participants */}
@@ -318,7 +323,8 @@ export function GroupChatRightPanel({
                   participant={participant}
                   state={sessionState}
                   color={participantColors[participant.name]}
-                  onJumpToSession={onJumpToSession}
+                  groupChatId={groupChatId}
+                  onContextReset={handleContextReset}
                 />
               );
             })

src/renderer/components/HistoryDetailModal.tsx

@@ -1,6 +1,7 @@
 import React, { useEffect, useRef, useState, useCallback } from 'react';
 import { X, Bot, User, Copy, Check, CheckCircle, XCircle, Trash2, Clock, Cpu, Zap, Play, ChevronLeft, ChevronRight } from 'lucide-react';
 import type { Theme, HistoryEntry } from '../types';
+import type { FileNode } from '../types/fileTree';
 import { useLayerStack } from '../contexts/LayerStackContext';
 import { MODAL_PRIORITIES } from '../constants/modalPriorities';
 import { formatElapsedTime } from '../utils/formatters';
@@ -27,6 +28,11 @@ interface HistoryDetailModalProps {
   filteredEntries?: HistoryEntry[];
   currentIndex?: number;
   onNavigate?: (entry: HistoryEntry, index: number) => void;
+  // File linking props for markdown rendering
+  fileTree?: FileNode[];
+  cwd?: string;
+  projectRoot?: string;
+  onFileClick?: (path: string) => void;
 }
 
 // Get context bar color based on usage percentage
@@ -46,7 +52,11 @@ export function HistoryDetailModal({
   onUpdate,
   filteredEntries,
   currentIndex,
-  onNavigate
+  onNavigate,
+  fileTree,
+  cwd,
+  projectRoot,
+  onFileClick
 }: HistoryDetailModalProps) {
   const { registerLayer, unregisterLayer, updateLayerHandler } = useLayerStack();
   const layerIdRef = useRef<string>();
@@ -403,6 +413,10 @@ export function HistoryDetailModal({
             content={cleanResponse}
             theme={theme}
             onCopy={(text) => navigator.clipboard.writeText(text)}
+            fileTree={fileTree}
+            cwd={cwd}
+            projectRoot={projectRoot}
+            onFileClick={onFileClick}
           />
         </div>
 

src/renderer/components/HistoryPanel.tsx

@@ -399,6 +399,9 @@ interface HistoryPanelProps {
   onResumeSession?: (agentSessionId: string) => void;
   onOpenSessionAsTab?: (agentSessionId: string) => void;
   onOpenAboutModal?: () => void;  // For opening About/achievements panel from history entries
+  // File linking props for history detail modal
+  fileTree?: any[];
+  onFileClick?: (path: string) => void;
 }
 
 export interface HistoryPanelHandle {
@@ -414,7 +417,7 @@ const LOAD_MORE_COUNT = 50;         // Entries to add when scrolling
 // Module-level storage for scroll positions (persists across session switches)
 const scrollPositionCache = new Map<string, number>();
 
-export const HistoryPanel = React.memo(forwardRef<HistoryPanelHandle, HistoryPanelProps>(function HistoryPanel({ session, theme, onJumpToAgentSession, onResumeSession, onOpenSessionAsTab, onOpenAboutModal }, ref) {
+export const HistoryPanel = React.memo(forwardRef<HistoryPanelHandle, HistoryPanelProps>(function HistoryPanel({ session, theme, onJumpToAgentSession, onResumeSession, onOpenSessionAsTab, onOpenAboutModal, fileTree, onFileClick }, ref) {
   const [historyEntries, setHistoryEntries] = useState<HistoryEntry[]>([]);
   const [activeFilters, setActiveFilters] = useState<Set<HistoryEntryType>>(new Set(['AUTO', 'USER']));
   const [isLoading, setIsLoading] = useState(true);
@@ -1120,6 +1123,11 @@ export const HistoryPanel = React.memo(forwardRef<HistoryPanelHandle, HistoryPan
               setDisplayCount(Math.min(index + LOAD_MORE_COUNT, allFilteredEntries.length));
             }
           }}
+          // File linking props for markdown rendering
+          fileTree={fileTree}
+          cwd={session.cwd}
+          projectRoot={session.projectRoot}
+          onFileClick={onFileClick}
         />
       )}
 

src/renderer/components/MarkdownRenderer.tsx

@@ -1,6 +1,7 @@
 import React, { memo, useMemo, useState, useEffect } from 'react';
 import ReactMarkdown from 'react-markdown';
 import remarkGfm from 'remark-gfm';
+import rehypeRaw from 'rehype-raw';
 import { Prism as SyntaxHighlighter } from 'react-syntax-highlighter';
 import { vscDarkPlus } from 'react-syntax-highlighter/dist/esm/styles/prism';
 import { Clipboard, Loader2, ImageOff } from 'lucide-react';
@@ -220,6 +221,7 @@ export const MarkdownRenderer = memo(({ content, theme, onCopy, className = '',
     >
       <ReactMarkdown
         remarkPlugins={remarkPlugins}
+        rehypePlugins={[rehypeRaw]}
         components={{
           a: ({ node, href, children, ...props }) => {
             // Check for maestro-file:// protocol OR data-maestro-file attribute

src/renderer/components/ParticipantCard.tsx

@@ -5,7 +5,8 @@
  * session ID, context usage, stats, and cost.
  */
 
-import { MessageSquare, ExternalLink, DollarSign } from 'lucide-react';
+import { MessageSquare, Copy, Check, DollarSign, RotateCcw } from 'lucide-react';
+import { useState, useCallback } from 'react';
 import type { Theme, GroupChatParticipant, SessionState } from '../types';
 import { getStatusColor } from '../utils/theme';
 import { formatCost } from '../utils/formatters';
@@ -15,8 +16,8 @@ interface ParticipantCardProps {
   participant: GroupChatParticipant;
   state: SessionState;
   color?: string;
-  /** Callback when user clicks session ID pill to jump to the agent */
-  onJumpToSession?: (sessionId: string) => void;
+  groupChatId?: string;
+  onContextReset?: (participantName: string) => void;
 }
 
 /**
@@ -35,17 +36,23 @@ export function ParticipantCard({
   participant,
   state,
   color,
-  onJumpToSession,
+  groupChatId,
+  onContextReset,
 }: ParticipantCardProps): JSX.Element {
+  const [copied, setCopied] = useState(false);
+  const [isResetting, setIsResetting] = useState(false);
+
   // Use agent's session ID (clean GUID) when available, otherwise show pending
   const agentSessionId = participant.agentSessionId;
   const isPending = !agentSessionId;
 
-  const handleJumpToSession = () => {
-    if (onJumpToSession && participant.sessionId) {
-      onJumpToSession(participant.sessionId);
+  const copySessionId = useCallback(() => {
+    if (agentSessionId) {
+      navigator.clipboard.writeText(agentSessionId);
+      setCopied(true);
+      setTimeout(() => setCopied(false), 2000);
     }
-  };
+  }, [agentSessionId]);
 
   // Determine if state should animate (busy or connecting)
   const shouldPulse = state === 'busy' || state === 'connecting';
@@ -66,6 +73,19 @@ export function ParticipantCard({
   // Context usage percentage (default to 0 if not set)
   const contextUsage = participant.contextUsage ?? 0;
 
+  // Show reset button when context usage is 40% or higher
+  const showResetButton = contextUsage >= 40 && onContextReset && groupChatId && !isResetting;
+
+  const handleReset = useCallback(async () => {
+    if (!onContextReset || !groupChatId) return;
+    setIsResetting(true);
+    try {
+      await onContextReset(participant.name);
+    } finally {
+      setIsResetting(false);
+    }
+  }, [onContextReset, groupChatId, participant.name]);
+
   return (
     <div
       className="rounded-lg border p-3"
@@ -105,19 +125,23 @@ export function ParticipantCard({
           </span>
         ) : (
           <button
-            onClick={handleJumpToSession}
+            onClick={copySessionId}
             className="flex items-center gap-1 text-[10px] px-2 py-0.5 rounded-full hover:opacity-80 transition-opacity cursor-pointer shrink-0"
             style={{
               backgroundColor: `${theme.colors.accent}20`,
               color: theme.colors.accent,
               border: `1px solid ${theme.colors.accent}40`,
             }}
-            title={`Session: ${agentSessionId}\nClick to jump to agent`}
+            title={`Session: ${agentSessionId}\nClick to copy`}
           >
             <span className="font-mono">
               {agentSessionId.slice(0, 8).toUpperCase()}
             </span>
-            <ExternalLink className="w-2.5 h-2.5" />
+            {copied ? (
+              <Check className="w-2.5 h-2.5" />
+            ) : (
+              <Copy className="w-2.5 h-2.5" />
+            )}
           </button>
         )}
       </div>
@@ -190,6 +214,35 @@ export function ParticipantCard({
             {formatCost(participant.totalCost).slice(1)}
           </span>
         )}
+        {/* Reset button - shown when context usage >= 40% */}
+        {showResetButton && (
+          <button
+            onClick={handleReset}
+            className="flex items-center gap-0.5 text-[10px] px-1.5 py-0.5 rounded shrink-0 hover:opacity-80 transition-opacity cursor-pointer"
+            style={{
+              backgroundColor: `${theme.colors.warning}20`,
+              color: theme.colors.warning,
+              border: `1px solid ${theme.colors.warning}40`,
+            }}
+            title="Reset context: Summarize current session and start fresh"
+          >
+            <RotateCcw className="w-3 h-3" />
+            Reset
+          </button>
+        )}
+        {/* Reset in progress indicator */}
+        {isResetting && (
+          <span
+            className="flex items-center gap-0.5 text-[10px] px-1.5 py-0.5 rounded shrink-0 animate-pulse"
+            style={{
+              backgroundColor: `${theme.colors.warning}20`,
+              color: theme.colors.warning,
+            }}
+          >
+            <RotateCcw className="w-3 h-3 animate-spin" />
+            Resetting...
+          </span>
+        )}
       </div>
     </div>
   );

src/renderer/components/RightPanel.tsx

@@ -93,6 +93,8 @@ interface RightPanelProps {
   onResumeSession?: (agentSessionId: string) => void;
   onOpenSessionAsTab?: (agentSessionId: string) => void;
   onOpenAboutModal?: () => void;  // For opening About/achievements panel from history entries
+  // File linking callback for history detail modal
+  onFileClick?: (path: string) => void;
 }
 
 export const RightPanel = forwardRef<RightPanelHandle, RightPanelProps>(function RightPanel(props, ref) {
@@ -112,7 +114,7 @@ export const RightPanel = forwardRef<RightPanelHandle, RightPanelProps>(function
     // Error handling callbacks (Phase 5.10)
     onSkipCurrentDocument, onAbortBatchOnError, onResumeAfterError,
     onJumpToAgentSession, onResumeSession,
-    onOpenSessionAsTab, onOpenAboutModal
+    onOpenSessionAsTab, onOpenAboutModal, onFileClick
   } = props;
 
   const historyPanelRef = useRef<HistoryPanelHandle>(null);
@@ -461,6 +463,8 @@ export const RightPanel = forwardRef<RightPanelHandle, RightPanelProps>(function
               onResumeSession={onResumeSession}
               onOpenSessionAsTab={onOpenSessionAsTab}
               onOpenAboutModal={onOpenAboutModal}
+              fileTree={filteredFileTree}
+              onFileClick={onFileClick}
             />
           </div>
         )}

src/renderer/global.d.ts

@@ -990,6 +990,7 @@ interface MaestroAPI {
     }>;
     sendToParticipant: (id: string, name: string, message: string, images?: string[]) => Promise<void>;
     removeParticipant: (id: string, name: string) => Promise<void>;
+    resetParticipantContext: (id: string, name: string, cwd?: string) => Promise<{ newAgentSessionId: string }>;
     // History
     getHistory: (id: string) => Promise<Array<{
       id: string;