diff --git a/package-lock.json b/package-lock.json
index 138c05b..47d5e50 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -9,9 +9,10 @@
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+        "cliui": "^6.0.0",
+        "decamelize": "^1.2.0",
+        "find-up": "^4.1.0",
+        "get-caller-file": "^2.0.1",
+        "require-directory": "^2.1.1",
+        "require-main-filename": "^2.0.0",
+        "set-blocking": "^2.0.0",
+        "string-width": "^4.2.0",
+        "which-module": "^2.0.0",
+        "y18n": "^4.0.0",
+        "yargs-parser": "^18.1.2"
+      },
+      "engines": {
+        "node": ">=8"
+      }
+    },
+    "node_modules/yargs-parser": {
+      "version": "18.1.3",
+      "resolved": "https://registry.npmjs.org/yargs-parser/-/yargs-parser-18.1.3.tgz",
+      "integrity": "sha512-o50j0JeToy/4K6OZcaQmW6lyXXKhq7csREXcDwk2omFPJEwUNOVtJKvmDr9EI1fAJZUyZcRF7kxGBWmRXudrCQ==",
+      "license": "ISC",
+      "dependencies": {
+        "camelcase": "^5.0.0",
+        "decamelize": "^1.2.0"
+      },
+      "engines": {
+        "node": ">=6"
+      }
+    },
+    "node_modules/yargs/node_modules/find-up": {
+      "version": "4.1.0",
+      "resolved": "https://registry.npmjs.org/find-up/-/find-up-4.1.0.tgz",
+      "integrity": "sha512-PpOwAdQ/YlXQ2vj8a3h8IipDuYRi3wceVQQGYWxNINccq40Anw7BlsEXCMbt1Zt+OLA6Fq9suIpIWD0OsnISlw==",
+      "license": "MIT",
+      "dependencies": {
+        "locate-path": "^5.0.0",
+        "path-exists": "^4.0.0"
+      },
+      "engines": {
+        "node": ">=8"
+      }
+    },
+    "node_modules/yargs/node_modules/locate-path": {
+      "version": "5.0.0",
+      "resolved": "https://registry.npmjs.org/locate-path/-/locate-path-5.0.0.tgz",
+      "integrity": "sha512-t7hw9pI+WvuwNJXwk5zVHpyhIqzg2qTlklJOf0mVxGSbe3Fp2VieZcduNYjaLDoy6p9uGpQEGWG87WpMKlNq8g==",
+      "license": "MIT",
+      "dependencies": {
+        "p-locate": "^4.1.0"
+      },
+      "engines": {
+        "node": ">=8"
+      }
+    },
+    "node_modules/yargs/node_modules/p-limit": {
+      "version": "2.3.0",
+      "resolved": "https://registry.npmjs.org/p-limit/-/p-limit-2.3.0.tgz",
+      "integrity": "sha512-//88mFWSJx8lxCzwdAABTJL2MyWB12+eIY7MDL2SqLmAkeKU9qxRvWuSyTjm3FUmpBEMuFfckAIqEaVGUDxb6w==",
+      "license": "MIT",
+      "dependencies": {
+        "p-try": "^2.0.0"
+      },
+      "engines": {
+        "node": ">=6"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/sindresorhus"
+      }
+    },
+    "node_modules/yargs/node_modules/p-locate": {
+      "version": "4.1.0",
+      "resolved": "https://registry.npmjs.org/p-locate/-/p-locate-4.1.0.tgz",
+      "integrity": "sha512-R79ZZ/0wAxKGu3oYMlz8jy/kbhsNrS7SKZ7PxEHBgJ5+F2mtFW2fK2cOtBh1cHYkQsbzFV7I+EoRKe6Yt0oK7A==",
+      "license": "MIT",
+      "dependencies": {
+        "p-limit": "^2.2.0"
+      },
+      "engines": {
+        "node": ">=8"
+      }
+    },
     "node_modules/yocto-queue": {
       "version": "0.1.0",
       "resolved": "https://registry.npmjs.org/yocto-queue/-/yocto-queue-0.1.0.tgz",
       "integrity": "sha512-rVksvsnNCdJ/ohGc6xgPwyN8eheCxsiLM8mxuE/t/mOVqJewPuO1miLpTHQiRgTKCLexL4MeAFVagts7HmNZ2Q==",
-      "dev": true,
       "engines": {
         "node": ">=10"
       },
diff --git a/package.json b/package.json
index 3cabe31..a96e583 100644
--- a/package.json
+++ b/package.json
@@ -22,9 +22,10 @@
   },
   "dependencies": {
     "@onecli-sh/sdk": "^0.2.0",
-    "@whiskeysockets/baileys": "^6.7.16",
+    "@whiskeysockets/baileys": "^6.17.16",
     "better-sqlite3": "11.10.0",
     "cron-parser": "5.5.0",
+    "qrcode": "^1.5.4",
     "qrcode-terminal": "^0.12.0"
   },
   "devDependencies": {
diff --git a/src/channels/whatsapp.test.ts b/src/channels/whatsapp.test.ts
index 5bf1893..8ad0371 100644
--- a/src/channels/whatsapp.test.ts
+++ b/src/channels/whatsapp.test.ts
@@ -23,6 +23,7 @@ vi.mock('../logger.js', () => ({
 // Mock db
 vi.mock('../db.js', () => ({
   getLastGroupSync: vi.fn(() => null),
+  getMessageContentById: vi.fn(() => undefined),
   setLastGroupSync: vi.fn(),
   updateChatName: vi.fn(),
 }));
@@ -74,6 +75,7 @@ let fakeSocket: ReturnType<typeof createFakeSocket>;
 vi.mock('@whiskeysockets/baileys', () => {
   return {
     default: vi.fn(() => fakeSocket),
+    makeWASocket: vi.fn(() => fakeSocket),
     Browsers: { macOS: vi.fn(() => ['macOS', 'Chrome', '']) },
     DisconnectReason: {
       loggedOut: 401,
diff --git a/src/channels/whatsapp.ts b/src/channels/whatsapp.ts
index 6710436..195424c 100644
--- a/src/channels/whatsapp.ts
+++ b/src/channels/whatsapp.ts
@@ -2,24 +2,26 @@ import { exec } from 'child_process';
 import fs from 'fs';
 import path from 'path';
 
-import makeWASocket, {
+import {
+  makeWASocket,
   Browsers,
   DisconnectReason,
-  WAMessageKey,
-  WASocket,
   fetchLatestWaWebVersion,
   makeCacheableSignalKeyStore,
   normalizeMessageContent,
-  proto,
   useMultiFileAuthState,
 } from '@whiskeysockets/baileys';
+import type { GroupMetadata, WAMessageKey, WASocket, proto as ProtoTypes } from '@whiskeysockets/baileys';
+// proto is not statically analyzable as a named ESM export from this CJS module
+import { createRequire } from 'module';
+const { proto } = createRequire(import.meta.url)('@whiskeysockets/baileys') as { proto: typeof ProtoTypes };
 
 import {
   ASSISTANT_HAS_OWN_NUMBER,
   ASSISTANT_NAME,
   STORE_DIR,
 } from '../config.js';
-import { getLastGroupSync, setLastGroupSync, updateChatName } from '../db.js';
+import { getLastGroupSync, getMessageContentById, setLastGroupSync, updateChatName } from '../db.js';
 import { logger } from '../logger.js';
 import pino from 'pino';
 
@@ -51,9 +53,16 @@ export class WhatsAppChannel implements Channel {
   private flushing = false;
   private groupSyncTimerStarted = false;
   /** Cache of recently sent messages for retry requests (max 256 entries). */
-  private sentMessageCache = new Map<string, proto.IMessage>();
+  private sentMessageCache = new Map<string, ProtoTypes.IMessage>();
+  /** Short-lived cache of phone-normalized group metadata for outbound sends. */
+  private groupMetadataCache = new Map<
+    string,
+    { metadata: GroupMetadata; expiresAt: number }
+  >();
   /** Bot's LID user ID (e.g. "80355281346633") for normalizing group mentions. */
   private botLidUser?: string;
+  /** Resolve the initial connect() once the first successful open happens. */
+  private pendingFirstOpen?: () => void;
 
   private opts: WhatsAppChannelOpts;
 
@@ -63,11 +72,12 @@ export class WhatsAppChannel implements Channel {
 
   async connect(): Promise<void> {
     return new Promise<void>((resolve, reject) => {
-      this.connectInternal(resolve).catch(reject);
+      this.pendingFirstOpen = resolve;
+      this.connectInternal().catch(reject);
     });
   }
 
-  private async connectInternal(onFirstOpen?: () => void): Promise<void> {
+  private async connectInternal(): Promise<void> {
     const authDir = path.join(STORE_DIR, 'auth');
     fs.mkdirSync(authDir, { recursive: true });
 
@@ -89,14 +99,26 @@ export class WhatsAppChannel implements Channel {
       printQRInTerminal: false,
       logger: baileysLogger,
       browser: Browsers.macOS('Chrome'),
+      cachedGroupMetadata: async (jid: string) =>
+        this.getNormalizedGroupMetadata(jid),
       getMessage: async (key: WAMessageKey) => {
         const cached = this.sentMessageCache.get(key.id || '');
         if (cached) {
           logger.debug({ id: key.id }, 'getMessage: returning cached message for retry');
           return cached;
         }
-        logger.debug({ id: key.id }, 'getMessage: no cached message found');
-        return undefined;
+        // Fall back to DB lookup so WhatsApp can re-encrypt on retry.
+        // Without this, self-chat messages show "waiting for this message".
+        const content = key.id && key.remoteJid
+          ? getMessageContentById(key.id, key.remoteJid)
+          : undefined;
+        if (content) {
+          logger.debug({ id: key.id }, 'getMessage: returning DB message for retry');
+          return proto.Message.fromObject({ conversation: content });
+        }
+        // Return empty message rather than undefined — prevents indefinite
+        // "waiting for this message" when we genuinely don't have the content.
+        return proto.Message.fromObject({});
       },
     });
 
@@ -156,7 +178,7 @@ export class WhatsAppChannel implements Channel {
           const phoneUser = this.sock.user.id.split(':')[0];
           const lidUser = this.sock.user.lid?.split(':')[0];
           if (lidUser && phoneUser) {
-            this.lidToPhoneMap[lidUser] = `${phoneUser}@s.whatsapp.net`;
+            this.setLidPhoneMapping(lidUser, `${phoneUser}@s.whatsapp.net`);
             this.botLidUser = lidUser;
             logger.debug({ lidUser, phoneUser }, 'LID to phone mapping set');
           }
@@ -182,15 +204,22 @@ export class WhatsAppChannel implements Channel {
         }
 
         // Signal first connection to caller
-        if (onFirstOpen) {
-          onFirstOpen();
-          onFirstOpen = undefined;
+        if (this.pendingFirstOpen) {
+          this.pendingFirstOpen();
+          this.pendingFirstOpen = undefined;
         }
       }
     });
 
     this.sock.ev.on('creds.update', saveCreds);
 
+    this.sock.ev.on('chats.phoneNumberShare', ({ lid, jid }) => {
+      const lidUser = lid?.split('@')[0].split(':')[0];
+      if (lidUser && jid) {
+        this.setLidPhoneMapping(lidUser, jid);
+      }
+    });
+
     this.sock.ev.on('messages.upsert', async ({ messages }) => {
       for (const msg of messages) {
         try {
@@ -210,7 +239,10 @@ export class WhatsAppChannel implements Channel {
           if (chatJid.endsWith('@lid') && (msg.key as any).senderPn) {
             const pn = (msg.key as any).senderPn as string;
             const phoneJid = pn.includes('@') ? pn : `${pn}@s.whatsapp.net`;
-            this.lidToPhoneMap[rawJid.split('@')[0].split(':')[0]] = phoneJid;
+            this.setLidPhoneMapping(
+              rawJid.split('@')[0].split(':')[0],
+              phoneJid,
+            );
             chatJid = phoneJid;
             logger.info({ lidJid: rawJid, phoneJid }, 'Translated LID via senderPn');
           }
@@ -407,7 +439,7 @@ export class WhatsAppChannel implements Channel {
       const pn = await (this.sock.signalRepository as any)?.lidMapping?.getPNForLID(jid);
       if (pn) {
         const phoneJid = `${pn.split('@')[0].split(':')[0]}@s.whatsapp.net`;
-        this.lidToPhoneMap[lidUser] = phoneJid;
+        this.setLidPhoneMapping(lidUser, phoneJid);
         logger.info(
           { lidJid: jid, phoneJid },
           'Translated LID to phone JID (signalRepository)',
@@ -421,6 +453,48 @@ export class WhatsAppChannel implements Channel {
     return jid;
   }
 
+  private setLidPhoneMapping(lidUser: string, phoneJid: string): void {
+    if (this.lidToPhoneMap[lidUser] === phoneJid) return;
+    this.lidToPhoneMap[lidUser] = phoneJid;
+    // Participant IDs in cached group metadata depend on this mapping.
+    this.groupMetadataCache.clear();
+  }
+
+  private async getNormalizedGroupMetadata(
+    jid: string,
+    forceRefresh = false,
+  ): Promise<GroupMetadata | undefined> {
+    if (!jid.endsWith('@g.us')) return undefined;
+
+    const cached = this.groupMetadataCache.get(jid);
+    if (!forceRefresh && cached && cached.expiresAt > Date.now()) {
+      return cached.metadata;
+    }
+
+    const metadata = await this.sock.groupMetadata(jid);
+    const participants = await Promise.all(
+      metadata.participants.map(async (participant) => ({
+        ...participant,
+        id: await this.translateJid(participant.id),
+      })),
+    );
+    const normalized = { ...metadata, participants };
+    const mappedCount = participants.filter(
+      (participant, index) => participant.id !== metadata.participants[index]?.id,
+    ).length;
+
+    logger.info(
+      { jid, participantCount: participants.length, mappedCount },
+      'Prepared normalized group metadata for send',
+    );
+
+    this.groupMetadataCache.set(jid, {
+      metadata: normalized,
+      expiresAt: Date.now() + 60_000,
+    });
+    return normalized;
+  }
+
   private async flushOutgoingQueue(): Promise<void> {
     if (this.flushing || this.outgoingQueue.length === 0) return;
     this.flushing = true;
diff --git a/src/db.ts b/src/db.ts
index 7fba354..c9f0759 100644
--- a/src/db.ts
+++ b/src/db.ts
@@ -388,6 +388,16 @@ export function getLastBotMessageTimestamp(
   return row?.ts ?? undefined;
 }
 
+export function getMessageContentById(
+  id: string,
+  chatJid: string,
+): string | undefined {
+  const row = db
+    .prepare(`SELECT content FROM messages WHERE id = ? AND chat_jid = ?`)
+    .get(id, chatJid) as { content: string } | undefined;
+  return row?.content;
+}
+
 export function createTask(
   task: Omit<ScheduledTask, 'last_run' | 'last_result'>,
 ): void {
diff --git a/src/whatsapp-auth.ts b/src/whatsapp-auth.ts
index ccf0c36..41c9b42 100644
--- a/src/whatsapp-auth.ts
+++ b/src/whatsapp-auth.ts
@@ -13,7 +13,8 @@ import pino from 'pino';
 import qrcode from 'qrcode-terminal';
 import readline from 'readline';
 
-import makeWASocket, {
+import {
+  makeWASocket,
   Browsers,
   DisconnectReason,
   fetchLatestWaWebVersion,