diff --git a/index.d.ts b/index.d.ts
index 631d8bc..9fc11bb 100644
--- a/index.d.ts
+++ b/index.d.ts
@@ -546,6 +546,15 @@ declare namespace WAWebJS {
             ) => void,
         ): this;
 
+        /** Emitted when a ciphertext message failed to decrypt after recovery attempt */
+        on(
+            event: 'message_ciphertext_failed',
+            listener: (
+                /** The message that failed to decrypt */
+                message: Message,
+            ) => void,
+        ): this;
+
         /** Emitted when a message is deleted for everyone in the chat */
         on(
             event: 'message_revoke_everyone',
@@ -999,6 +1008,7 @@ declare namespace WAWebJS {
         CHAT_ARCHIVED = 'chat_archived',
         MESSAGE_RECEIVED = 'message',
         MESSAGE_CIPHERTEXT = 'message_ciphertext',
+        MESSAGE_CIPHERTEXT_FAILED = 'message_ciphertext_failed',
         MESSAGE_CREATE = 'message_create',
         MESSAGE_REVOKED_EVERYONE = 'message_revoke_everyone',
         MESSAGE_REVOKED_ME = 'message_revoke_me',
diff --git a/src/Client.js b/src/Client.js
index ed2392d..145e110 100644
--- a/src/Client.js
+++ b/src/Client.js
@@ -980,7 +980,7 @@ class Client extends EventEmitter {
             'onAddMessageCiphertextEvent',
             (msg) => {
                 /**
-                 * Emitted when messages are edited
+                 * Emitted when a message is received as ciphertext (not yet decrypted)
                  * @event Client#message_ciphertext
                  * @param {Message} message
                  */
@@ -988,6 +988,22 @@ class Client extends EventEmitter {
             },
         );
 
+        await exposeFunctionIfAbsent(
+            this.pupPage,
+            'onCiphertextFailedEvent',
+            (msg) => {
+                /**
+                 * Emitted when a ciphertext message failed to decrypt after recovery attempt
+                 * @event Client#message_ciphertext_failed
+                 * @param {Message} message
+                 */
+                this.emit(
+                    Events.MESSAGE_CIPHERTEXT_FAILED,
+                    new Message(this, msg),
+                );
+            },
+        );
+
         await exposeFunctionIfAbsent(
             this.pupPage,
             'onPollVoteEvent',
@@ -1007,6 +1023,11 @@ class Client extends EventEmitter {
             const { Msg, Chat, WAWebCallCollection } =
                 window.require('WAWebCollections');
             const AppState = window.require('WAWebSocketModel').Socket;
+
+            // Enable placeholder message resend (recovery for ciphertext messages)
+            const gatingUtils = window.require('WAWebSyncGatingUtils');
+            gatingUtils.isPlaceholderMessageResendEnabled = () => true;
+
             Msg.on('change', (msg) => {
                 window.onChangeMessageEvent(window.WWebJS.getMessageModel(msg));
             });
@@ -1068,24 +1089,59 @@ class Client extends EventEmitter {
                     prevState,
                 );
             });
+            const pendingResend = new Set();
+            let resendFlush = null;
+
+            function requestResend(msg) {
+                pendingResend.add(msg);
+                if (resendFlush) return;
+                resendFlush = setTimeout(() => {
+                    resendFlush = null;
+                    const msgs = [...pendingResend];
+                    pendingResend.clear();
+                    if (msgs.length === 0) return;
+                    window
+                        .require(
+                            'WAWebNonMessageDataRequestPlaceholderMessageResendUtils',
+                        )
+                        .handlePlaceholderMsgsSeen(msgs, true);
+                }, 5000);
+            }
+
             Msg.on('add', (msg) => {
-                if (msg.isNewMsg) {
-                    if (msg.type === 'ciphertext') {
-                        // defer message event until ciphertext is resolved (type changed)
-                        msg.once('change:type', (_msg) =>
-                            window.onAddMessageEvent(
-                                window.WWebJS.getMessageModel(_msg),
-                            ),
-                        );
-                        window.onAddMessageCiphertextEvent(
-                            window.WWebJS.getMessageModel(msg),
-                        );
-                    } else {
-                        window.onAddMessageEvent(
-                            window.WWebJS.getMessageModel(msg),
-                        );
-                    }
+                if (!msg.isNewMsg) return;
+
+                if (msg.type !== 'ciphertext') {
+                    window.onAddMessageEvent(
+                        window.WWebJS.getMessageModel(msg),
+                    );
+                    return;
                 }
+
+                window.onAddMessageCiphertextEvent(
+                    window.WWebJS.getMessageModel(msg),
+                );
+
+                if (msg.subtype && msg.subtype.endsWith('_unavailable_fanout'))
+                    return;
+
+                requestResend(msg);
+
+                const failTimer = setTimeout(() => {
+                    if (msg.type !== 'ciphertext') return;
+                    window.onCiphertextFailedEvent(
+                        window.WWebJS.getMessageModel(msg),
+                    );
+                }, 15000);
+
+                msg.once('change:type', (_msg) => {
+                    clearTimeout(failTimer);
+                    pendingResend.delete(_msg);
+                    if (_msg.type === 'revoked') return;
+                    window.onAddMessageEvent(
+                        window.WWebJS.getMessageModel(_msg),
+                    );
+                });
             });
             Chat.on('change:unreadCount', (chat) => {
                 window.onChatUnreadCountEvent(chat);
diff --git a/src/util/Constants.js b/src/util/Constants.js
index 65e757f..f883020 100644
--- a/src/util/Constants.js
+++ b/src/util/Constants.js
@@ -51,6 +51,7 @@ exports.Events = {
     CHAT_ARCHIVED: 'chat_archived',
     MESSAGE_RECEIVED: 'message',
     MESSAGE_CIPHERTEXT: 'message_ciphertext',
+    MESSAGE_CIPHERTEXT_FAILED: 'message_ciphertext_failed',
     MESSAGE_CREATE: 'message_create',
     MESSAGE_REVOKED_EVERYONE: 'message_revoke_everyone',
     MESSAGE_REVOKED_ME: 'message_revoke_me',