diff --git a/src/whatsapp/models/message.model.ts b/src/whatsapp/models/message.model.ts
index 395b100b..2b59f3a5 100644
--- a/src/whatsapp/models/message.model.ts
+++ b/src/whatsapp/models/message.model.ts
@@ -10,6 +10,12 @@ class Key {
   participant?: string;
 }
 
+class ChatwootMessage {
+  messageId?: number;
+  inboxId?: number;
+  conversationId?: number;
+}
+
 export class MessageRaw {
   _id?: string;
   key?: Key;
@@ -22,7 +28,7 @@ export class MessageRaw {
   source?: 'android' | 'web' | 'ios';
   source_id?: string;
   source_reply_id?: string;
-  chatwootMessageId?: string;
+  chatwoot?: ChatwootMessage;
 }
 
 const messageSchema = new Schema<MessageRaw>({
@@ -40,10 +46,14 @@ const messageSchema = new Schema<MessageRaw>({
   source: { type: String, minlength: 3, enum: ['android', 'web', 'ios'] },
   messageTimestamp: { type: Number, required: true },
   owner: { type: String, required: true, minlength: 1 },
-  chatwootMessageId: { type: String, required: false },
+  chatwoot: {
+    messageId: { type: Number },
+    inboxId: { type: Number },
+    conversationId: { type: Number },
+  },
 });
 
-messageSchema.index({ chatwootMessageId: 1, owner: 1 });
+messageSchema.index({ 'chatwoot.messageId': 1, owner: 1 });
 messageSchema.index({ 'key.id': 1 });
 messageSchema.index({ 'key.id': 1, owner: 1 });
 messageSchema.index({ owner: 1 });
diff --git a/src/whatsapp/repository/message.repository.ts b/src/whatsapp/repository/message.repository.ts
index e212ca3d..d7675977 100644
--- a/src/whatsapp/repository/message.repository.ts
+++ b/src/whatsapp/repository/message.repository.ts
@@ -91,11 +91,13 @@ export class MessageRepository extends Repository {
       this.logger.verbose('finding messages');
       if (this.dbSettings.ENABLED) {
         this.logger.verbose('finding messages in db');
-        if (query?.where?.key) {
-          for (const [k, v] of Object.entries(query.where.key)) {
-            query.where['key.' + k] = v;
+        for (const [o, p] of Object.entries(query?.where)) {
+          if (typeof p === 'object' && p !== null && !Array.isArray(p)) {
+            for (const [k, v] of Object.entries(p)) {
+              query.where[`${o}.${k}`] = v;
+            }
+            delete query.where[o];
           }
-          delete query?.where?.key;
         }
 
         return await this.messageModel
diff --git a/src/whatsapp/services/chatwoot.service.ts b/src/whatsapp/services/chatwoot.service.ts
index ccd01347..26b0cce9 100644
--- a/src/whatsapp/services/chatwoot.service.ts
+++ b/src/whatsapp/services/chatwoot.service.ts
@@ -14,6 +14,7 @@ import { InstanceDto } from '../dto/instance.dto';
 import { Options, Quoted, SendAudioDto, SendMediaDto, SendTextDto } from '../dto/sendMessage.dto';
 import { MessageRaw } from '../models';
 import { RepositoryBroker } from '../repository/repository.manager';
+import { Events } from '../types/wa.types';
 import { WAMonitoringService } from './monitor.service';
 
 export class ChatwootService {
@@ -1036,7 +1037,9 @@ export class ChatwootService {
         const message = await this.repository.message.find({
           where: {
             owner: instance.instanceName,
-            chatwootMessageId: body.id,
+            chatwoot: {
+              messageId: body.id,
+            },
           },
           limit: 1,
         });
@@ -1160,7 +1163,11 @@ export class ChatwootService {
                   ...messageSent,
                   owner: instance.instanceName,
                 },
-                body.id,
+                {
+                  messageId: body.id,
+                  inboxId: body.inbox?.id,
+                  conversationId: body.conversation?.id,
+                },
                 instance,
               );
             }
@@ -1187,7 +1194,11 @@ export class ChatwootService {
                 ...messageSent,
                 owner: instance.instanceName,
               },
-              body.id,
+              {
+                messageId: body.id,
+                inboxId: body.inbox?.id,
+                conversationId: body.conversation?.id,
+              },
               instance,
             );
           }
@@ -1221,15 +1232,33 @@ export class ChatwootService {
     }
   }
 
-  private updateChatwootMessageId(message: MessageRaw, chatwootMessageId: string, instance: InstanceDto) {
-    if (!chatwootMessageId || !message?.key?.id) {
+  private updateChatwootMessageId(
+    message: MessageRaw,
+    chatwootMessageIds: MessageRaw['chatwoot'],
+    instance: InstanceDto,
+  ) {
+    if (!chatwootMessageIds.messageId || !message?.key?.id) {
       return;
     }
 
-    message.chatwootMessageId = chatwootMessageId;
+    message.chatwoot = chatwootMessageIds;
     this.repository.message.update([message], instance.instanceName, true);
   }
 
+  private async getMessageByKeyId(instance: InstanceDto, keyId: string): Promise<MessageRaw> {
+    const messages = await this.repository.message.find({
+      where: {
+        key: {
+          id: keyId,
+        },
+        owner: instance.instanceName,
+      },
+      limit: 1,
+    });
+
+    return messages.length ? messages[0] : null;
+  }
+
   private async getReplyToIds(
     msg: any,
     instance: InstanceDto,
@@ -1240,17 +1269,9 @@ export class ChatwootService {
     if (msg) {
       inReplyToExternalId = msg.message?.extendedTextMessage?.contextInfo?.stanzaId;
       if (inReplyToExternalId) {
-        const message = await this.repository.message.find({
-          where: {
-            key: {
-              id: inReplyToExternalId,
-            },
-            owner: instance.instanceName,
-          },
-          limit: 1,
-        });
-        if (message.length && message[0]?.chatwootMessageId) {
-          inReplyTo = message[0].chatwootMessageId;
+        const message = await this.getMessageByKeyId(instance, inReplyToExternalId);
+        if (message?.chatwoot?.messageId) {
+          inReplyTo = message.chatwoot.messageId;
         }
       }
     }
@@ -1265,7 +1286,9 @@ export class ChatwootService {
     if (msg?.content_attributes?.in_reply_to) {
       const message = await this.repository.message.find({
         where: {
-          chatwootMessageId: msg?.content_attributes?.in_reply_to,
+          chatwoot: {
+            messageId: msg?.content_attributes?.in_reply_to,
+          },
           owner: instance.instanceName,
         },
         limit: 1,
@@ -1757,6 +1780,25 @@ export class ChatwootService {
         }
       }
 
+      if (event === Events.MESSAGES_DELETE) {
+        this.logger.verbose('deleting message from instance: ' + instance.instanceName);
+
+        if (!body?.key?.id) {
+          this.logger.warn('message id not found');
+          return;
+        }
+
+        const message = await this.getMessageByKeyId(instance, body.key.id);
+        if (message?.chatwoot?.messageId && message?.chatwoot?.conversationId) {
+          this.logger.verbose('deleting message in chatwoot. Message id: ' + body.key.id);
+          return await client.messages.delete({
+            accountId: this.provider.account_id,
+            conversationId: message.chatwoot.conversationId,
+            messageId: message.chatwoot.messageId,
+          });
+        }
+      }
+
       if (event === 'status.instance') {
         this.logger.verbose('event status.instance');
         const data = body;
diff --git a/src/whatsapp/services/whatsapp.service.ts b/src/whatsapp/services/whatsapp.service.ts
index 35c763bb..1e1d5b88 100644
--- a/src/whatsapp/services/whatsapp.service.ts
+++ b/src/whatsapp/services/whatsapp.service.ts
@@ -1798,7 +1798,11 @@ export class WAStartupService {
             );
 
             if (chatwootSentMessage?.id) {
-              messageRaw.chatwootMessageId = chatwootSentMessage.id;
+              messageRaw.chatwoot = {
+                messageId: chatwootSentMessage.id,
+                inboxId: chatwootSentMessage.inbox_id,
+                conversationId: chatwootSentMessage.conversation_id,
+              };
             }
           }
 
@@ -1941,6 +1945,22 @@ export class WAStartupService {
               this.instance.name,
               database.SAVE_DATA.MESSAGE_UPDATE,
             );
+
+            if (this.localChatwoot.enabled) {
+              this.chatwootService.eventWhatsapp(
+                Events.MESSAGES_DELETE,
+                { instanceName: this.instance.name },
+                {
+                  key: {
+                    remoteJid: key.remoteJid,
+                    fromMe: key.fromMe,
+                    id: key.id,
+                    participant: key.participant,
+                  },
+                },
+              );
+            }
+
             return;
           }