diff --git a/frontend_tests/node_tests/upload.js b/frontend_tests/node_tests/upload.js
index 81e198ea7a..32c4a2165d 100644
--- a/frontend_tests/node_tests/upload.js
+++ b/frontend_tests/node_tests/upload.js
@@ -146,7 +146,7 @@ run_test('show_error_message', () => {
 
 run_test('upload_files', () => {
     let uppy_cancel_all_called = false;
-    const files = [
+    let files = [
         {
             name: "budapest.png",
             type: "image/png",
@@ -212,6 +212,25 @@ run_test('upload_files', () => {
     assert(compose_ui_autosize_textarea_called);
     assert(uppy_add_file_called);
 
+    files = [
+        {
+            name: "budapest.png",
+            type: "image/png",
+        },
+        {
+            name: "prague.png",
+            type: "image/png",
+        },
+    ];
+    let add_file_counter = 0;
+    uppy.addFile = (file) => {
+        assert.equal(file.name, "budapest.png");
+        add_file_counter += 1;
+        throw Error();
+    };
+    upload.upload_files(uppy, config, files);
+    assert.equal(add_file_counter, 1);
+
     global.patch_builtin("setTimeout", (func) => {
         func();
     });
diff --git a/static/js/upload.js b/static/js/upload.js
index 4ae627fc0f..70f01c1c28 100644
--- a/static/js/upload.js
+++ b/static/js/upload.js
@@ -119,6 +119,7 @@ exports.upload_files = function (uppy, config, files) {
             });
         } catch (error) {
             // Errors are handled by info-visible and upload-error event callbacks.
+            break;
         }
     }
 };