diff --git a/plugins/chat/assets/javascripts/discourse/components/chat-composer-uploads.js b/plugins/chat/assets/javascripts/discourse/components/chat-composer-uploads.js
index 2b76d566810..a6b7f6568fc 100644
--- a/plugins/chat/assets/javascripts/discourse/components/chat-composer-uploads.js
+++ b/plugins/chat/assets/javascripts/discourse/components/chat-composer-uploads.js
@@ -26,7 +26,7 @@ export default Component.extend(UppyUploadMixin, {
 
   didReceiveAttrs() {
     this._super(...arguments);
-    if (this._uppyInstance?.getState?.()?.totalProgress > 0) {
+    if (this.inProgressUploads?.length > 0) {
       this._uppyInstance?.cancelAll();
     }
 
@@ -53,7 +53,7 @@ export default Component.extend(UppyUploadMixin, {
 
   uploadDone(upload) {
     this.uploads.pushObject(upload);
-    this.onUploadChanged(this.uploads);
+    this._triggerUploadsChanged();
   },
 
   @discourseComputed("uploads.length", "inProgressUploads.length")
@@ -67,13 +67,13 @@ export default Component.extend(UppyUploadMixin, {
       fileId: upload.id,
     });
     this.uploads.removeObject(upload);
-    this.onUploadChanged(this.uploads);
+    this._triggerUploadsChanged();
   },
 
   @action
   removeUpload(upload) {
     this.uploads.removeObject(upload);
-    this.onUploadChanged(this.uploads);
+    this._triggerUploadsChanged();
   },
 
   _uploadDropTargetOptions() {
@@ -134,4 +134,10 @@ export default Component.extend(UppyUploadMixin, {
       this._addFiles([...event.clipboardData.files], { pasted: true });
     }
   },
+
+  _triggerUploadsChanged() {
+    this.onUploadChanged(this.uploads, {
+      inProgressUploadsCount: this.inProgressUploads?.length,
+    });
+  },
 });
diff --git a/plugins/chat/assets/javascripts/discourse/components/chat-composer.js b/plugins/chat/assets/javascripts/discourse/components/chat-composer.js
index b66d897dee1..eb7d434c4db 100644
--- a/plugins/chat/assets/javascripts/discourse/components/chat-composer.js
+++ b/plugins/chat/assets/javascripts/discourse/components/chat-composer.js
@@ -719,9 +719,9 @@ export default Component.extend(TextareaTextManipulation, {
   },
 
   @action
-  uploadsChanged(uploads) {
+  uploadsChanged(uploads, { inProgressUploadsCount }) {
     this.set("_uploads", cloneJSON(uploads));
-    this.onValueChange?.({ uploads: this._uploads });
+    this.onValueChange?.({ uploads: this._uploads, inProgressUploadsCount });
   },
 
   @action
diff --git a/plugins/chat/assets/javascripts/discourse/components/chat-live-pane.js b/plugins/chat/assets/javascripts/discourse/components/chat-live-pane.js
index 817a1c4cc2f..f3d303c3f55 100644
--- a/plugins/chat/assets/javascripts/discourse/components/chat-live-pane.js
+++ b/plugins/chat/assets/javascripts/discourse/components/chat-live-pane.js
@@ -1005,14 +1005,24 @@ export default class ChatLivePane extends Component {
   }
 
   @action
-  composerValueChanged({ value, uploads, replyToMsg }) {
+  composerValueChanged({ value, uploads, replyToMsg, inProgressUploadsCount }) {
     if (!this.editingMessage && !this.args.channel.isDraft) {
       if (typeof value !== "undefined") {
         this.args.channel.draft.message = value;
       }
-      if (typeof uploads !== "undefined") {
+
+      // only save the uploads to the draft if we are not still uploading other
+      // ones, otherwise we get into a cycle where we pass the draft uploads as
+      // existingUploads back to the upload component and cause in progress ones
+      // to be cancelled
+      if (
+        typeof uploads !== "undefined" &&
+        inProgressUploadsCount !== "undefined" &&
+        inProgressUploadsCount === 0
+      ) {
         this.args.channel.draft.uploads = uploads;
       }
+
       if (typeof replyToMsg !== "undefined") {
         this.args.channel.draft.replyToMsg = replyToMsg;
       }
diff --git a/plugins/chat/spec/system/uploads_spec.rb b/plugins/chat/spec/system/uploads_spec.rb
index 09dee0e400d..90bcb05d4f7 100644
--- a/plugins/chat/spec/system/uploads_spec.rb
+++ b/plugins/chat/spec/system/uploads_spec.rb
@@ -38,17 +38,10 @@ describe "Uploading files in chat messages", type: :system, js: true do
       chat.visit_channel(channel_1)
 
       file_path_1 = file_from_fixtures("logo.png", "images").path
-      attach_file([file_path_1]) do
-        channel.open_action_menu
-        channel.click_action_button("chat-upload-btn")
-        find(".chat-composer-input").click
-      end
-
       file_path_2 = file_from_fixtures("logo.jpg", "images").path
-      attach_file([file_path_2]) do
+      attach_file([file_path_1, file_path_2]) do
         channel.open_action_menu
         channel.click_action_button("chat-upload-btn")
-        find(".chat-composer-input").click
       end
 
       expect(page).to have_css(".chat-composer-upload .preview .preview-img", count: 2)