diff --git a/src/cascadia/TerminalApp/TerminalPage.cpp b/src/cascadia/TerminalApp/TerminalPage.cpp
index fad50d69455..254a198e1dc 100644
--- a/src/cascadia/TerminalApp/TerminalPage.cpp
+++ b/src/cascadia/TerminalApp/TerminalPage.cpp
@@ -1359,8 +1359,9 @@ namespace winrt::TerminalApp::implementation
     //   than one tab opened, show a warning dialog.
     void TerminalPage::CloseWindow()
     {
-        if (_tabs.Size() > 1 && _settings.GlobalSettings().ConfirmCloseAllTabs())
+        if (_tabs.Size() > 1 && _settings.GlobalSettings().ConfirmCloseAllTabs() && !_displayingCloseDialog)
         {
+            _displayingCloseDialog = true;
             _ShowCloseWarningDialog();
         }
         else
@@ -2030,6 +2031,20 @@ namespace winrt::TerminalApp::implementation
         _CloseAllTabs();
     }
 
+    // Method Description:
+    // - Called when the close button of the content dialog is clicked.
+    //   This resets the flag _displayingCloseDialog, which was set before
+    //   opening the dialog. Otherwise, the Terminal app would be closed
+    //   on the next close request without showing the warning dialog.
+    // Arguments:
+    // - sender: unused
+    // - ContentDialogButtonClickEventArgs: unused
+    void TerminalPage::_CloseWarningCloseButtonOnClick(WUX::Controls::ContentDialog /* sender */,
+                                                       WUX::Controls::ContentDialogButtonClickEventArgs /* eventArgs*/)
+    {
+        _displayingCloseDialog = false;
+    }
+
     // Method Description:
     // - Hook up keybindings, and refresh the UI of the terminal.
     //   This includes update the settings of all the tabs according
diff --git a/src/cascadia/TerminalApp/TerminalPage.h b/src/cascadia/TerminalApp/TerminalPage.h
index 8b28ab12397..ac773366a00 100644
--- a/src/cascadia/TerminalApp/TerminalPage.h
+++ b/src/cascadia/TerminalApp/TerminalPage.h
@@ -124,10 +124,12 @@ namespace winrt::TerminalApp::implementation
         void _CreateNewTabFromSettings(GUID profileGuid, TerminalApp::TerminalSettings settings);
         winrt::Microsoft::Terminal::TerminalConnection::ITerminalConnection _CreateConnectionFromSettings(GUID profileGuid, TerminalApp::TerminalSettings settings);
 
+        bool _displayingCloseDialog{ false };
         void _SettingsButtonOnClick(const IInspectable& sender, const Windows::UI::Xaml::RoutedEventArgs& eventArgs);
         void _FeedbackButtonOnClick(const IInspectable& sender, const Windows::UI::Xaml::RoutedEventArgs& eventArgs);
         void _AboutButtonOnClick(const IInspectable& sender, const Windows::UI::Xaml::RoutedEventArgs& eventArgs);
         void _CloseWarningPrimaryButtonOnClick(Windows::UI::Xaml::Controls::ContentDialog sender, Windows::UI::Xaml::Controls::ContentDialogButtonClickEventArgs eventArgs);
+        void _CloseWarningCloseButtonOnClick(Windows::UI::Xaml::Controls::ContentDialog sender, Windows::UI::Xaml::Controls::ContentDialogButtonClickEventArgs eventArgs);
         void _ThirdPartyNoticesOnClick(const IInspectable& sender, const Windows::UI::Xaml::RoutedEventArgs& eventArgs);
 
         void _HookupKeyBindings(const Microsoft::Terminal::Settings::Model::KeyMapping& keymap) noexcept;
diff --git a/src/cascadia/TerminalApp/TerminalPage.xaml b/src/cascadia/TerminalApp/TerminalPage.xaml
index b2901440bf4..e43a0c8672f 100644
--- a/src/cascadia/TerminalApp/TerminalPage.xaml
+++ b/src/cascadia/TerminalApp/TerminalPage.xaml
@@ -51,7 +51,8 @@ the MIT License. See LICENSE in the project root for license information. -->
             x:Name="CloseAllDialog"
             x:Uid="CloseAllDialog"
             DefaultButton="Primary"
-            PrimaryButtonClick="_CloseWarningPrimaryButtonOnClick">
+            PrimaryButtonClick="_CloseWarningPrimaryButtonOnClick"
+            CloseButtonClick="_CloseWarningCloseButtonOnClick">
         </ContentDialog>
 
         <ContentDialog