diff --git a/Userland/Applications/TextEditor/MainWidget.cpp b/Userland/Applications/TextEditor/MainWidget.cpp
index ecc82b10b0..3de8612dff 100644
--- a/Userland/Applications/TextEditor/MainWidget.cpp
+++ b/Userland/Applications/TextEditor/MainWidget.cpp
@@ -672,6 +672,8 @@ bool MainWidget::request_close()
 
     if (result == GUI::MessageBox::ExecYes) {
         m_save_action->activate();
+        if (editor().document().is_modified())
+            return false;
         return true;
     }
 
diff --git a/Userland/DevTools/Playground/main.cpp b/Userland/DevTools/Playground/main.cpp
index fcaa94181c..b65d65b9a4 100644
--- a/Userland/DevTools/Playground/main.cpp
+++ b/Userland/DevTools/Playground/main.cpp
@@ -251,6 +251,8 @@ int main(int argc, char** argv)
         auto result = GUI::MessageBox::show(window, "The document has been modified. Would you like to save?", "Unsaved changes", GUI::MessageBox::Type::Warning, GUI::MessageBox::InputType::YesNoCancel);
         if (result == GUI::MessageBox::ExecYes) {
             save_action->activate();
+            if (window->is_modified())
+                return GUI::Window::CloseRequestDecision::StayOpen;
             return GUI::Window::CloseRequestDecision::Close;
         }