diff --git a/src/cascadia/TerminalApp/AppLogic.cpp b/src/cascadia/TerminalApp/AppLogic.cpp
index fc63fc0cc37..71698f7c4c2 100644
--- a/src/cascadia/TerminalApp/AppLogic.cpp
+++ b/src/cascadia/TerminalApp/AppLogic.cpp
@@ -396,6 +396,14 @@ namespace winrt::TerminalApp::implementation
         }
     }
 
+    // Method Description:
+    // - Returns true if there is no dialog currently being shown (meaning that we can show a dialog)
+    // - Returns false if there is a dialog currently being shown (meaning that we cannot show another dialog)
+    bool AppLogic::CanShowDialog()
+    {
+        return (_dialog == nullptr);
+    }
+
     // Method Description:
     // - Displays a dialog for errors found while loading or validating the
     //   settings. Uses the resources under the provided  title and content keys
diff --git a/src/cascadia/TerminalApp/AppLogic.h b/src/cascadia/TerminalApp/AppLogic.h
index 1d43f113ba5..582866704b4 100644
--- a/src/cascadia/TerminalApp/AppLogic.h
+++ b/src/cascadia/TerminalApp/AppLogic.h
@@ -122,6 +122,7 @@ namespace winrt::TerminalApp::implementation
         bool GetShowTitleInTitlebar();
 
         winrt::Windows::Foundation::IAsyncOperation<winrt::Windows::UI::Xaml::Controls::ContentDialogResult> ShowDialog(winrt::Windows::UI::Xaml::Controls::ContentDialog dialog);
+        bool CanShowDialog();
         void DismissDialog();
 
         Windows::Foundation::Collections::IMapView<Microsoft::Terminal::Control::KeyChord, Microsoft::Terminal::Settings::Model::Command> GlobalHotkeys();
diff --git a/src/cascadia/TerminalApp/AppLogic.idl b/src/cascadia/TerminalApp/AppLogic.idl
index 57e7a914e25..df0f7b3cd47 100644
--- a/src/cascadia/TerminalApp/AppLogic.idl
+++ b/src/cascadia/TerminalApp/AppLogic.idl
@@ -33,6 +33,8 @@ namespace TerminalApp
         SystemMenuItemHandler Handler { get; };
     };
 
+    // See IDialogPresenter and TerminalPage's DialogPresenter for more
+    // information.
     [default_interface] runtimeclass AppLogic : IDirectKeyListener, IDialogPresenter
     {
         AppLogic();
@@ -106,11 +108,6 @@ namespace TerminalApp
 
         Windows.Foundation.Collections.IMapView<Microsoft.Terminal.Control.KeyChord, Microsoft.Terminal.Settings.Model.Command> GlobalHotkeys();
 
-        // See IDialogPresenter and TerminalPage's DialogPresenter for more
-        // information.
-        Windows.Foundation.IAsyncOperation<Windows.UI.Xaml.Controls.ContentDialogResult> ShowDialog(Windows.UI.Xaml.Controls.ContentDialog dialog);
-        void DismissDialog();
-
         event Windows.Foundation.TypedEventHandler<Object, Windows.UI.Xaml.UIElement> SetTitleBarContent;
         event Windows.Foundation.TypedEventHandler<Object, String> TitleChanged;
         event Windows.Foundation.TypedEventHandler<Object, LastTabClosedEventArgs> LastTabClosed;
diff --git a/src/cascadia/TerminalApp/TerminalPage.cpp b/src/cascadia/TerminalApp/TerminalPage.cpp
index 19ccaa195e0..8f79e9b8090 100644
--- a/src/cascadia/TerminalApp/TerminalPage.cpp
+++ b/src/cascadia/TerminalApp/TerminalPage.cpp
@@ -685,10 +685,7 @@ namespace winrt::TerminalApp::implementation
     //   Notes link, and privacy policy link.
     void TerminalPage::_ShowAboutDialog()
     {
-        if (auto presenter{ _dialogPresenter.get() })
-        {
-            presenter.ShowDialog(FindName(L"AboutDialog").try_as<WUX::Controls::ContentDialog>());
-        }
+        _ShowDialogHelper(L"AboutDialog");
     }
 
     winrt::hstring TerminalPage::ApplicationDisplayName()
@@ -708,6 +705,33 @@ namespace winrt::TerminalApp::implementation
         ShellExecute(nullptr, nullptr, currentPath.c_str(), nullptr, nullptr, SW_SHOW);
     }
 
+    // Method description:
+    // - Called when the user closes a content dialog
+    // - Tells the presenter to update its knowledge of whether there is a content dialog open
+    void TerminalPage::_DialogCloseClick(const IInspectable&,
+                                         const ContentDialogButtonClickEventArgs&)
+    {
+        if (auto presenter{ _dialogPresenter.get() })
+        {
+            presenter.DismissDialog();
+        }
+    }
+
+    // Method Description:
+    // - Helper to show a content dialog
+    // - We only open a content dialog if there isn't one open already
+    winrt::Windows::Foundation::IAsyncOperation<ContentDialogResult> TerminalPage::_ShowDialogHelper(const std::wstring_view& name)
+    {
+        if (auto presenter{ _dialogPresenter.get() })
+        {
+            if (presenter.CanShowDialog())
+            {
+                co_return co_await presenter.ShowDialog(FindName(name).try_as<WUX::Controls::ContentDialog>());
+            }
+        }
+        co_return ContentDialogResult::None;
+    }
+
     // Method Description:
     // - Displays a dialog to warn the user that they are about to close all open windows.
     //   Once the user clicks the OK button, shut down the application.
@@ -716,11 +740,7 @@ namespace winrt::TerminalApp::implementation
     //   when this is called, nothing happens. See _ShowDialog for details
     winrt::Windows::Foundation::IAsyncOperation<ContentDialogResult> TerminalPage::_ShowQuitDialog()
     {
-        if (auto presenter{ _dialogPresenter.get() })
-        {
-            co_return co_await presenter.ShowDialog(FindName(L"QuitDialog").try_as<WUX::Controls::ContentDialog>());
-        }
-        co_return ContentDialogResult::None;
+        return _ShowDialogHelper(L"QuitDialog");
     }
 
     // Method Description:
@@ -732,22 +752,14 @@ namespace winrt::TerminalApp::implementation
     //   when this is called, nothing happens. See _ShowDialog for details
     winrt::Windows::Foundation::IAsyncOperation<ContentDialogResult> TerminalPage::_ShowCloseWarningDialog()
     {
-        if (auto presenter{ _dialogPresenter.get() })
-        {
-            co_return co_await presenter.ShowDialog(FindName(L"CloseAllDialog").try_as<WUX::Controls::ContentDialog>());
-        }
-        co_return ContentDialogResult::None;
+        return _ShowDialogHelper(L"CloseAllDialog");
     }
 
     // Method Description:
     // - Displays a dialog for warnings found while closing the terminal tab marked as read-only
     winrt::Windows::Foundation::IAsyncOperation<ContentDialogResult> TerminalPage::_ShowCloseReadOnlyDialog()
     {
-        if (auto presenter{ _dialogPresenter.get() })
-        {
-            co_return co_await presenter.ShowDialog(FindName(L"CloseReadOnlyDialog").try_as<WUX::Controls::ContentDialog>());
-        }
-        co_return ContentDialogResult::None;
+        return _ShowDialogHelper(L"CloseReadOnlyDialog");
     }
 
     // Method Description:
@@ -760,11 +772,7 @@ namespace winrt::TerminalApp::implementation
     //   when this is called, nothing happens. See _ShowDialog for details
     winrt::Windows::Foundation::IAsyncOperation<ContentDialogResult> TerminalPage::_ShowMultiLinePasteWarningDialog()
     {
-        if (auto presenter{ _dialogPresenter.get() })
-        {
-            co_return co_await presenter.ShowDialog(FindName(L"MultiLinePasteDialog").try_as<WUX::Controls::ContentDialog>());
-        }
-        co_return ContentDialogResult::None;
+        return _ShowDialogHelper(L"MultiLinePasteDialog");
     }
 
     // Method Description:
@@ -775,11 +783,7 @@ namespace winrt::TerminalApp::implementation
     //   when this is called, nothing happens. See _ShowDialog for details
     winrt::Windows::Foundation::IAsyncOperation<ContentDialogResult> TerminalPage::_ShowLargePasteWarningDialog()
     {
-        if (auto presenter{ _dialogPresenter.get() })
-        {
-            co_return co_await presenter.ShowDialog(FindName(L"LargePasteDialog").try_as<WUX::Controls::ContentDialog>());
-        }
-        co_return ContentDialogResult::None;
+        return _ShowDialogHelper(L"LargePasteDialog");
     }
 
     // Method Description:
diff --git a/src/cascadia/TerminalApp/TerminalPage.h b/src/cascadia/TerminalApp/TerminalPage.h
index a1867178590..2e48d9db883 100644
--- a/src/cascadia/TerminalApp/TerminalPage.h
+++ b/src/cascadia/TerminalApp/TerminalPage.h
@@ -215,12 +215,15 @@ namespace winrt::TerminalApp::implementation
         std::shared_ptr<Toast> _windowIdToast{ nullptr };
         std::shared_ptr<Toast> _windowRenameFailedToast{ nullptr };
 
+        winrt::Windows::Foundation::IAsyncOperation<winrt::Windows::UI::Xaml::Controls::ContentDialogResult> _ShowDialogHelper(const std::wstring_view& name);
+
         void _ShowAboutDialog();
         winrt::Windows::Foundation::IAsyncOperation<winrt::Windows::UI::Xaml::Controls::ContentDialogResult> _ShowQuitDialog();
         winrt::Windows::Foundation::IAsyncOperation<winrt::Windows::UI::Xaml::Controls::ContentDialogResult> _ShowCloseWarningDialog();
         winrt::Windows::Foundation::IAsyncOperation<winrt::Windows::UI::Xaml::Controls::ContentDialogResult> _ShowCloseReadOnlyDialog();
         winrt::Windows::Foundation::IAsyncOperation<winrt::Windows::UI::Xaml::Controls::ContentDialogResult> _ShowMultiLinePasteWarningDialog();
         winrt::Windows::Foundation::IAsyncOperation<winrt::Windows::UI::Xaml::Controls::ContentDialogResult> _ShowLargePasteWarningDialog();
+        void _DialogCloseClick(const IInspectable& sender, const Windows::UI::Xaml::Controls::ContentDialogButtonClickEventArgs& eventArgs);
 
         void _CreateNewTabFlyout();
         void _OpenNewTabDropdown();
diff --git a/src/cascadia/TerminalApp/TerminalPage.idl b/src/cascadia/TerminalApp/TerminalPage.idl
index 979483d0ad8..b726fcf23ef 100644
--- a/src/cascadia/TerminalApp/TerminalPage.idl
+++ b/src/cascadia/TerminalApp/TerminalPage.idl
@@ -14,6 +14,8 @@ namespace TerminalApp
     interface IDialogPresenter
     {
         Windows.Foundation.IAsyncOperation<Windows.UI.Xaml.Controls.ContentDialogResult> ShowDialog(Windows.UI.Xaml.Controls.ContentDialog dialog);
+        Boolean CanShowDialog();
+        void DismissDialog();
     };
 
     [default_interface] runtimeclass TerminalPage : Windows.UI.Xaml.Controls.Page, Windows.UI.Xaml.Data.INotifyPropertyChanged
diff --git a/src/cascadia/TerminalApp/TerminalPage.xaml b/src/cascadia/TerminalApp/TerminalPage.xaml
index f7855356634..5ca8ed25858 100644
--- a/src/cascadia/TerminalApp/TerminalPage.xaml
+++ b/src/cascadia/TerminalApp/TerminalPage.xaml
@@ -75,6 +75,7 @@
         <ContentDialog x:Name="AboutDialog"
                        x:Uid="AboutDialog"
                        x:Load="False"
+                       CloseButtonClick="_DialogCloseClick"
                        DefaultButton="Close">
             <StackPanel Orientation="Vertical">
                 <TextBlock IsTextSelectionEnabled="True">
@@ -96,21 +97,25 @@
         <ContentDialog x:Name="QuitDialog"
                        x:Uid="QuitDialog"
                        x:Load="False"
+                       CloseButtonClick="_DialogCloseClick"
                        DefaultButton="Primary" />
 
         <ContentDialog x:Name="CloseAllDialog"
                        x:Uid="CloseAllDialog"
                        x:Load="False"
+                       CloseButtonClick="_DialogCloseClick"
                        DefaultButton="Primary" />
 
         <ContentDialog x:Name="CloseReadOnlyDialog"
                        x:Uid="CloseReadOnlyDialog"
                        x:Load="False"
+                       CloseButtonClick="_DialogCloseClick"
                        DefaultButton="Close" />
 
         <ContentDialog x:Name="MultiLinePasteDialog"
                        x:Uid="MultiLinePasteDialog"
                        x:Load="False"
+                       CloseButtonClick="_DialogCloseClick"
                        DefaultButton="Primary">
             <StackPanel>
                 <TextBlock x:Uid="MultiLineWarningText"
@@ -130,11 +135,13 @@
         <ContentDialog x:Name="LargePasteDialog"
                        x:Uid="LargePasteDialog"
                        x:Load="False"
+                       CloseButtonClick="_DialogCloseClick"
                        DefaultButton="Primary" />
 
         <ContentDialog x:Name="ControlNoticeDialog"
                        x:Uid="ControlNoticeDialog"
                        x:Load="False"
+                       CloseButtonClick="_DialogCloseClick"
                        DefaultButton="Primary">
             <TextBlock IsTextSelectionEnabled="True"
                        TextWrapping="WrapWholeWords">
@@ -145,6 +152,7 @@
         <ContentDialog x:Name="CouldNotOpenUriDialog"
                        x:Uid="CouldNotOpenUriDialog"
                        x:Load="False"
+                       CloseButtonClick="_DialogCloseClick"
                        DefaultButton="Primary">
             <TextBlock IsTextSelectionEnabled="True"
                        TextWrapping="WrapWholeWords">