diff --git a/app/models/issue.rb b/app/models/issue.rb
index e920aea56..b4113b9fe 100644
--- a/app/models/issue.rb
+++ b/app/models/issue.rb
@@ -1958,6 +1958,8 @@ class Issue < ApplicationRecord
     if current_journal && !attachment.new_record?
       current_journal.journalize_attachment(attachment, :removed)
       current_journal.save
+      # Attachment removal via AJAX saves only the journal, so the usual issue update callback does not fire.
+      Webhook.trigger(event_name('updated'), self) unless saved_changes?
     end
   end
 
diff --git a/test/unit/webhook_test.rb b/test/unit/webhook_test.rb
index b9c6f2ad2..594d24c27 100644
--- a/test/unit/webhook_test.rb
+++ b/test/unit/webhook_test.rb
@@ -219,6 +219,20 @@ class WebhookTest < ActiveSupport::TestCase
     assert_equal @issue.id, payload.dig(:data, :issue, :id)
   end
 
+  test "should trigger issue updated webhook when attachment removal creates a journal without saving issue" do
+    issue = Issue.find(3)
+    attachment = Attachment.find(1)
+    issue.init_journal(@dlopper)
+
+    Webhook.expects(:trigger).with('issue.updated', issue).once
+    issue.attachments.delete(attachment)
+
+    journal = issue.journals.order(:id).last
+    assert_equal attachment.id.to_s, journal.details.last.prop_key
+    assert_equal 'attachment', journal.details.last.property
+    assert_equal attachment.filename, journal.details.last.old_value
+  end
+
   test "should compute correct signature" do
     # we're implementing the same signature mechanism as GitHub, so might as well re-use their
     # example. https://docs.github.com/en/webhooks/using-webhooks/validating-webhook-deliveries