diff --git a/src/api/integrations/chatwoot/services/chatwoot.service.ts b/src/api/integrations/chatwoot/services/chatwoot.service.ts
index e484ec66..a7a0e2f7 100644
--- a/src/api/integrations/chatwoot/services/chatwoot.service.ts
+++ b/src/api/integrations/chatwoot/services/chatwoot.service.ts
@@ -8,6 +8,7 @@ import ChatwootClient, {
   inbox,
 } from '@figuro/chatwoot-sdk';
 import { request as chatwootRequest } from '@figuro/chatwoot-sdk/dist/core/request';
+import { proto } from '@whiskeysockets/baileys';
 import axios from 'axios';
 import FormData from 'form-data';
 import { createReadStream, unlinkSync, writeFileSync } from 'fs';
@@ -628,7 +629,7 @@ export class ChatwootService {
         id: contactId,
       })) as any;
 
-      if (contactConversations) {
+      if (contactConversations?.payload?.length) {
         let conversation: any;
         if (this.provider.reopen_conversation) {
           conversation = contactConversations.payload.find((conversation) => conversation.inbox_id == filterInbox.id);
@@ -1106,6 +1107,26 @@ export class ChatwootService {
     }
   }
 
+  public async onSendMessageError(instance: InstanceDto, conversation: number, error?: string) {
+    const client = await this.clientCw(instance);
+
+    if (!client) {
+      return;
+    }
+
+    client.messages.create({
+      accountId: this.provider.account_id,
+      conversationId: conversation,
+      data: {
+        content: i18next.t('cw.message.notsent', {
+          error: error?.length > 0 ? `_${error}_` : '',
+        }),
+        message_type: 'outgoing',
+        private: true,
+      },
+    });
+  }
+
   public async receiveWebhook(instance: InstanceDto, body: any) {
     try {
       await new Promise((resolve) => setTimeout(resolve, 500));
@@ -1274,6 +1295,11 @@ export class ChatwootService {
           return { message: 'bot' };
         }
 
+        if (!waInstance && body.conversation?.id) {
+          this.onSendMessageError(instance, body.conversation?.id, 'Instance not found');
+          return { message: 'bot' };
+        }
+
         this.logger.verbose('Format message to send');
         let formatText: string;
         if (senderName === null || senderName === undefined) {
@@ -1310,6 +1336,9 @@ export class ChatwootService {
                 formatText,
                 options,
               );
+              if (!messageSent && body.conversation?.id) {
+                this.onSendMessageError(instance, body.conversation?.id);
+              }
 
               this.updateChatwootMessageId(
                 {
@@ -1343,23 +1372,34 @@ export class ChatwootService {
               },
             };
 
-            const messageSent = await waInstance?.textMessage(data, true);
+            let messageSent: MessageRaw | proto.WebMessageInfo;
+            try {
+              messageSent = await waInstance?.textMessage(data, true);
+              if (!messageSent) {
+                throw new Error('Message not sent');
+              }
 
-            this.updateChatwootMessageId(
-              {
-                ...messageSent,
-                owner: instance.instanceName,
-              },
-              {
-                messageId: body.id,
-                inboxId: body.inbox?.id,
-                conversationId: body.conversation?.id,
-                contactInbox: {
-                  sourceId: body.conversation?.contact_inbox?.source_id,
+              this.updateChatwootMessageId(
+                {
+                  ...messageSent,
+                  owner: instance.instanceName,
                 },
-              },
-              instance,
-            );
+                {
+                  messageId: body.id,
+                  inboxId: body.inbox?.id,
+                  conversationId: body.conversation?.id,
+                  contactInbox: {
+                    sourceId: body.conversation?.contact_inbox?.source_id,
+                  },
+                },
+                instance,
+              );
+            } catch (error) {
+              if (!messageSent && body.conversation?.id) {
+                this.onSendMessageError(instance, body.conversation?.id, error.toString());
+              }
+              throw error;
+            }
           }
         }
 
diff --git a/src/utils/translations/en.json b/src/utils/translations/en.json
index f0a64def..1b10e7b8 100644
--- a/src/utils/translations/en.json
+++ b/src/utils/translations/en.json
@@ -22,5 +22,6 @@
   "cw.contactMessage.contact": "Contact",
   "cw.contactMessage.name": "Name",
   "cw.contactMessage.number": "Number",
+  "cw.message.notsent": "🚨 The message could not be sent. Please check your connection. {{error}}",
   "cw.message.edited": "Edited Message"
 }
\ No newline at end of file
diff --git a/src/utils/translations/es.json b/src/utils/translations/es.json
index 28784063..13f0d4b7 100644
--- a/src/utils/translations/es.json
+++ b/src/utils/translations/es.json
@@ -22,5 +22,6 @@
   "cw.contactMessage.contact": "Contacto",
   "cw.contactMessage.name": "Nombre",
   "cw.contactMessage.number": "Numero",
+  "cw.message.notsent": "🚨 El mensaje no se pudo enviar. Comprueba tu conexión. {{error}}",
   "cw.message.edited": "Mensaje editado"
 }
\ No newline at end of file
diff --git a/src/utils/translations/pt-BR.json b/src/utils/translations/pt-BR.json
index a8d62417..85ed293b 100644
--- a/src/utils/translations/pt-BR.json
+++ b/src/utils/translations/pt-BR.json
@@ -22,5 +22,6 @@
   "cw.contactMessage.contact": "Contato",
   "cw.contactMessage.name": "Nome",
   "cw.contactMessage.number": "Número",
+  "cw.message.notsent": "🚨 Não foi possível enviar a mensagem. Verifique sua conexão. {{error}}",
   "cw.message.edited": "Mensagem editada"
 }
\ No newline at end of file