diff --git a/packages/twenty-server/src/modules/messaging/message-import-manager/services/messaging-message.service.ts b/packages/twenty-server/src/modules/messaging/message-import-manager/services/messaging-message.service.ts
index 1a7a398fe..bdccd9ba8 100644
--- a/packages/twenty-server/src/modules/messaging/message-import-manager/services/messaging-message.service.ts
+++ b/packages/twenty-server/src/modules/messaging/message-import-manager/services/messaging-message.service.ts
@@ -62,19 +62,39 @@ export class MessagingMessageService {
       });
 
       if (existingMessage) {
-        await messageChannelMessageAssociationRepository.upsert(
-          {
-            messageChannelId,
-            messageId: existingMessage.id,
-            messageExternalId: message.externalId,
-            messageThreadExternalId: message.messageThreadExternalId,
-          },
-          {
-            conflictPaths: ['messageChannelId', 'messageId'],
-            indexPredicate: '"deletedAt" IS NULL',
-          },
-          transactionManager,
-        );
+        const existingAssociation =
+          await messageChannelMessageAssociationRepository.findOne(
+            {
+              where: {
+                messageChannelId,
+                messageId: existingMessage.id,
+              },
+            },
+            transactionManager,
+          );
+
+        if (existingAssociation) {
+          await messageChannelMessageAssociationRepository.update(
+            {
+              id: existingAssociation.id,
+            },
+            {
+              messageExternalId: message.externalId,
+              messageThreadExternalId: message.messageThreadExternalId,
+            },
+            transactionManager,
+          );
+        } else {
+          await messageChannelMessageAssociationRepository.insert(
+            {
+              messageChannelId,
+              messageId: existingMessage.id,
+              messageExternalId: message.externalId,
+              messageThreadExternalId: message.messageThreadExternalId,
+            },
+            transactionManager,
+          );
+        }
 
         continue;
       }