diff --git a/app/assets/javascripts/attachments.js b/app/assets/javascripts/attachments.js
index 1650386b8..9e6441a54 100644
--- a/app/assets/javascripts/attachments.js
+++ b/app/assets/javascripts/attachments.js
@@ -350,7 +350,10 @@ function copyImageFromClipboard(e) {
       // get input file in the closest form
       var inputEl = $(this).closest("form").find('input:file.filedrop');
       handleFileDropEvent.target = e.target;
-      addFile(inputEl, new File([file], filename, { type: file.type }), true);
+      if (addFile(inputEl, new File([file], filename, { type: file.type }), true) == null) {
+        window.alert(inputEl.data('max-number-of-files-message'));
+        break;
+      }
     }
   }
 }
diff --git a/test/system/issues_test.rb b/test/system/issues_test.rb
index ee7e4def9..4cd02bc14 100644
--- a/test/system/issues_test.rb
+++ b/test/system/issues_test.rb
@@ -174,6 +174,30 @@ class IssuesSystemTest < ApplicationSystemTestCase
     assert_equal 'Some description', issue.attachments.first.description
   end
 
+  def test_pasting_image_beyond_max_attachments_at_once_should_show_error
+    set_tmp_attachments_directory
+    log_user('jsmith', 'jsmith')
+
+    visit '/projects/ecookbook/issues/new'
+    paste_image = lambda do
+      page.execute_script(<<~JS)
+        // 1x1 1-bit grayscale PNG image
+        const png = Uint8Array.from(atob('iVBORw0KGgoAAAANSUhEUgAAAAEAAAABAQAAAAA3bvkkAAAACklEQVR42mNgAAAAAgAB5Sfe/AAAAABJRU5ErkJggg=='), c => c.charCodeAt(0));
+        const clipboardData = new DataTransfer();
+        clipboardData.items.add(new File([png], 'image.png', { type: 'image/png' }));
+        const event = new Event('paste', { bubbles: true, cancelable: true });
+        Object.defineProperty(event, 'clipboardData', { value: clipboardData });
+        document.getElementById('issue_description').dispatchEvent(event);
+      JS
+    end
+    10.times { paste_image.call }
+    assert_selector '.attachments_fields > span', :count => 10
+    accept_alert(/maximum number of files that can be attached simultaneously \(10\)/) do
+      paste_image.call
+    end
+    assert_selector '.attachments_fields > span', :count => 10
+  end
+
   def test_create_issue_with_new_target_version
     log_user('jsmith', 'jsmith')