diff --git a/packages/stream_chat/CHANGELOG.md b/packages/stream_chat/CHANGELOG.md
index fb5e53a74..10f4ae340 100644
--- a/packages/stream_chat/CHANGELOG.md
+++ b/packages/stream_chat/CHANGELOG.md
@@ -1,3 +1,9 @@
+## Upcoming
+
+🐞 Fixed
+
+- Fixed `toDraftMessage` to only include successfully uploaded attachments in draft messages.
+
 ## 9.16.0
 
 🐞 Fixed
diff --git a/packages/stream_chat/lib/src/core/models/draft_message.dart b/packages/stream_chat/lib/src/core/models/draft_message.dart
index d1e1a95c6..13c373475 100644
--- a/packages/stream_chat/lib/src/core/models/draft_message.dart
+++ b/packages/stream_chat/lib/src/core/models/draft_message.dart
@@ -189,11 +189,16 @@ extension MessageToDraftMessage on Message {
   /// This is useful when you want to convert a message to a draft message
   /// before sending it to the server.
   DraftMessage toDraftMessage() {
+    // Only include attachments that have been successfully uploaded.
+    final uploadedAttachments = attachments.where((it) {
+      return it.uploadState.isSuccess;
+    }).toList();
+
     return DraftMessage(
       id: id,
       text: text,
       type: type,
-      attachments: attachments,
+      attachments: uploadedAttachments,
       parentId: parentId,
       showInChannel: showInChannel,
       mentionedUsers: mentionedUsers,
diff --git a/packages/stream_chat/test/src/core/models/draft_message_test.dart b/packages/stream_chat/test/src/core/models/draft_message_test.dart
index 6450b0dc6..6542e8b4d 100644
--- a/packages/stream_chat/test/src/core/models/draft_message_test.dart
+++ b/packages/stream_chat/test/src/core/models/draft_message_test.dart
@@ -1,6 +1,7 @@
 // ignore_for_file: avoid_redundant_argument_values
 
 import 'package:stream_chat/src/core/models/attachment.dart';
+import 'package:stream_chat/src/core/models/attachment_file.dart';
 import 'package:stream_chat/src/core/models/draft_message.dart';
 import 'package:stream_chat/src/core/models/message.dart';
 import 'package:stream_chat/src/core/models/poll.dart';
@@ -303,8 +304,8 @@ void main() {
     group('Message and DraftMessage conversion', () {
       test('should convert Message to DraftMessage correctly', () {
         final attachments = [
-          Attachment(type: 'image'),
-          Attachment(type: 'file'),
+          Attachment(type: 'image', uploadState: const UploadState.success()),
+          Attachment(type: 'file', uploadState: const UploadState.success()),
         ];
         final mentionedUsers = [
           User(id: 'user1'),
@@ -355,10 +356,51 @@ void main() {
         expect(draftMessage.extraData, equals(message.extraData));
       });
 
+      test('should only include successfully uploaded attachments', () {
+        final successfulAttachment = Attachment(
+          id: 'success-attachment',
+          type: 'image',
+          uploadState: const UploadState.success(),
+        );
+        final preparingAttachment = Attachment(
+          id: 'preparing-attachment',
+          type: 'file',
+          uploadState: const UploadState.preparing(),
+        );
+        final inProgressAttachment = Attachment(
+          id: 'progress-attachment',
+          type: 'image',
+          uploadState: const UploadState.inProgress(uploaded: 50, total: 100),
+        );
+        final failedAttachment = Attachment(
+          id: 'failed-attachment',
+          type: 'file',
+          uploadState: const UploadState.failed(error: 'Upload failed'),
+        );
+
+        final message = Message(
+          id: 'test-message',
+          text: 'Test message with mixed upload states',
+          attachments: [
+            successfulAttachment,
+            preparingAttachment,
+            inProgressAttachment,
+            failedAttachment,
+          ],
+        );
+
+        final draftMessage = message.toDraftMessage();
+
+        // Only the successfully uploaded attachment should be included
+        expect(draftMessage.attachments.length, equals(1));
+        expect(draftMessage.attachments.first.id, equals('success-attachment'));
+        expect(draftMessage.attachments.first.uploadState.isSuccess, isTrue);
+      });
+
       test('should convert DraftMessage to Message correctly', () {
         final attachments = [
-          Attachment(type: 'image'),
-          Attachment(type: 'file'),
+          Attachment(type: 'image', uploadState: const UploadState.success()),
+          Attachment(type: 'file', uploadState: const UploadState.success()),
         ];
         final mentionedUsers = [
           User(id: 'user1'),