diff --git a/.gitignore b/.gitignore
index a3f626a5..d5e80c60 100644
--- a/.gitignore
+++ b/.gitignore
@@ -5,11 +5,17 @@ node_modules/
 # Auto Claude data directory and files
 .auto-claude/
 .auto-claude-*
+.auto-claude-security.json
+.auto-claude-status
 .claude_settings.json
 .worktrees/
 .security-key
 logs/security/
 
+# State persistence data (keep structure, ignore content)
+data/*
+!data/.gitkeep
+
 # Verification scripts
 verify-*.js
 VERIFICATION_GUIDE.md
diff --git a/data/.gitkeep b/data/.gitkeep
new file mode 100644
index 00000000..e69de29b
diff --git a/src/index.js b/src/index.js
index b17a13f0..55c421ea 100644
--- a/src/index.js
+++ b/src/index.js
@@ -7,11 +7,12 @@
  * - Welcome messages for new members
  * - Spam/scam detection and moderation
  * - Health monitoring and status command
+ * - Graceful shutdown handling
  */
 
 import { Client, GatewayIntentBits, Collection } from 'discord.js';
 import { config as dotenvConfig } from 'dotenv';
-import { readdirSync } from 'fs';
+import { readdirSync, writeFileSync, readFileSync, existsSync, mkdirSync } from 'fs';
 import { join, dirname } from 'path';
 import { fileURLToPath } from 'url';
 import { loadConfig } from './modules/config.js';
@@ -19,11 +20,16 @@ import { registerEventHandlers } from './modules/events.js';
 import { HealthMonitor } from './utils/health.js';
 import { registerCommands } from './utils/registerCommands.js';
 import { hasPermission, getPermissionError } from './utils/permissions.js';
+import { getConversationHistory, setConversationHistory } from './modules/ai.js';
 
 // ES module dirname equivalent
 const __filename = fileURLToPath(import.meta.url);
 const __dirname = dirname(__filename);
 
+// State persistence path
+const dataDir = join(__dirname, '..', 'data');
+const statePath = join(dataDir, 'state.json');
+
 // Load environment variables
 dotenvConfig();
 
@@ -46,6 +52,67 @@ client.commands = new Collection();
 // Initialize health monitor
 const healthMonitor = HealthMonitor.getInstance();
 
+// Track pending AI requests for graceful shutdown
+const pendingRequests = new Set();
+
+/**
+ * Register a pending request for tracking
+ * @returns {Symbol} Request ID to use for cleanup
+ */
+export function registerPendingRequest() {
+  const requestId = Symbol('request');
+  pendingRequests.add(requestId);
+  return requestId;
+}
+
+/**
+ * Remove a pending request from tracking
+ * @param {Symbol} requestId - Request ID to remove
+ */
+export function removePendingRequest(requestId) {
+  pendingRequests.delete(requestId);
+}
+
+/**
+ * Save conversation history to disk
+ */
+function saveState() {
+  try {
+    // Ensure data directory exists
+    if (!existsSync(dataDir)) {
+      mkdirSync(dataDir, { recursive: true });
+    }
+
+    const conversationHistory = getConversationHistory();
+    const stateData = {
+      conversationHistory: Array.from(conversationHistory.entries()),
+      timestamp: new Date().toISOString(),
+    };
+    writeFileSync(statePath, JSON.stringify(stateData, null, 2), 'utf-8');
+    console.log('💾 State saved successfully');
+  } catch (err) {
+    console.error('❌ Failed to save state:', err.message);
+  }
+}
+
+/**
+ * Load conversation history from disk
+ */
+function loadState() {
+  try {
+    if (!existsSync(statePath)) {
+      return;
+    }
+    const stateData = JSON.parse(readFileSync(statePath, 'utf-8'));
+    if (stateData.conversationHistory) {
+      setConversationHistory(new Map(stateData.conversationHistory));
+      console.log('📂 State loaded successfully');
+    }
+  } catch (err) {
+    console.error('❌ Failed to load state:', err.message);
+  }
+}
+
 /**
  * Load all commands from the commands directory
  */
@@ -137,6 +204,47 @@ client.on('interactionCreate', async (interaction) => {
   }
 });
 
+/**
+ * Graceful shutdown handler
+ * @param {string} signal - Signal that triggered shutdown
+ */
+async function gracefulShutdown(signal) {
+  console.log(`\n🛑 Received ${signal}, shutting down gracefully...`);
+
+  // 1. Wait for pending requests with timeout
+  const SHUTDOWN_TIMEOUT = 10000; // 10 seconds
+  if (pendingRequests.size > 0) {
+    console.log(`⏳ Waiting for ${pendingRequests.size} pending request(s)...`);
+    const startTime = Date.now();
+
+    while (pendingRequests.size > 0 && (Date.now() - startTime) < SHUTDOWN_TIMEOUT) {
+      await new Promise(resolve => setTimeout(resolve, 100));
+    }
+
+    if (pendingRequests.size > 0) {
+      console.log(`⚠️ Timeout: ${pendingRequests.size} request(s) still pending`);
+    } else {
+      console.log('✅ All requests completed');
+    }
+  }
+
+  // 2. Save state after pending requests complete
+  console.log('💾 Saving conversation state...');
+  saveState();
+
+  // 3. Destroy Discord client
+  console.log('🔌 Disconnecting from Discord...');
+  client.destroy();
+
+  // 4. Log clean exit
+  console.log('✅ Shutdown complete');
+  process.exit(0);
+}
+
+// Handle shutdown signals
+process.on('SIGTERM', () => gracefulShutdown('SIGTERM'));
+process.on('SIGINT', () => gracefulShutdown('SIGINT'));
+
 // Start bot
 const token = process.env.DISCORD_TOKEN;
 if (!token) {
@@ -144,6 +252,9 @@ if (!token) {
   process.exit(1);
 }
 
+// Load previous state on startup
+loadState();
+
 // Load commands and login
 loadCommands()
   .then(() => client.login(token))
diff --git a/src/modules/ai.js b/src/modules/ai.js
index 26adfedb..5ab922ab 100644
--- a/src/modules/ai.js
+++ b/src/modules/ai.js
@@ -4,9 +4,25 @@
  */
 
 // Conversation history per channel (simple in-memory store)
-const conversationHistory = new Map();
+let conversationHistory = new Map();
 const MAX_HISTORY = 20;
 
+/**
+ * Get the full conversation history map (for state persistence)
+ * @returns {Map} Conversation history map
+ */
+export function getConversationHistory() {
+  return conversationHistory;
+}
+
+/**
+ * Set the conversation history map (for state restoration)
+ * @param {Map} history - Conversation history map to restore
+ */
+export function setConversationHistory(history) {
+  conversationHistory = history;
+}
+
 // OpenClaw API endpoint
 const OPENCLAW_URL = process.env.OPENCLAW_URL || 'http://localhost:18789/v1/chat/completions';
 const OPENCLAW_TOKEN = process.env.OPENCLAW_TOKEN || '';