diff --git a/src/messages/messages.service.ts b/src/messages/messages.service.ts
index dcb35bb..aacbbc4 100644
--- a/src/messages/messages.service.ts
+++ b/src/messages/messages.service.ts
@@ -240,8 +240,15 @@ export class MessagesService {
     });
 
     // Update conversation with last message info and unread counts
-    const truncatedContent =
-      dto.content.length > 255 ? dto.content.substring(0, 252) + '...' : dto.content;
+    let truncatedContent: string;
+    if (dto.messageType === 'IMAGE') {
+      truncatedContent = 'Sent an image';
+    } else if (dto.messageType === 'FILE') {
+      truncatedContent = 'Sent a file';
+    } else {
+      truncatedContent =
+        dto.content.length > 255 ? dto.content.substring(0, 252) + '...' : dto.content;
+    }
 
     await this.prisma.conversation.update({
       where: { id: conversationId },