diff --git a/src/cascadia/TerminalApp/AppLogic.cpp b/src/cascadia/TerminalApp/AppLogic.cpp
index 72d7dae9cf2..fedcbe05944 100644
--- a/src/cascadia/TerminalApp/AppLogic.cpp
+++ b/src/cascadia/TerminalApp/AppLogic.cpp
@@ -615,6 +615,17 @@ namespace winrt::TerminalApp::implementation
         return _settings.GlobalSettings().ShowTabsInTitlebar();
     }
 
+    bool AppLogic::GetInitialAlwaysOnTop()
+    {
+        if (!_loadedInitialSettings)
+        {
+            // Load settings if we haven't already
+            LoadSettings();
+        }
+
+        return _settings.GlobalSettings().AlwaysOnTop();
+    }
+
     // Method Description:
     // - See Pane::CalcSnappedDimension
     float AppLogic::CalcSnappedDimension(const bool widthOrHeight, const float dimension) const
diff --git a/src/cascadia/TerminalApp/AppLogic.h b/src/cascadia/TerminalApp/AppLogic.h
index a6dfd3251cd..077982d8a58 100644
--- a/src/cascadia/TerminalApp/AppLogic.h
+++ b/src/cascadia/TerminalApp/AppLogic.h
@@ -41,6 +41,7 @@ namespace winrt::TerminalApp::implementation
         winrt::Windows::UI::Xaml::ElementTheme GetRequestedTheme();
         Microsoft::Terminal::Settings::Model::LaunchMode GetLaunchMode();
         bool GetShowTabsInTitlebar();
+        bool GetInitialAlwaysOnTop();
         float CalcSnappedDimension(const bool widthOrHeight, const float dimension) const;
 
         Windows::UI::Xaml::UIElement GetRoot() noexcept;
diff --git a/src/cascadia/TerminalApp/AppLogic.idl b/src/cascadia/TerminalApp/AppLogic.idl
index 683a038bbd9..7056f71b540 100644
--- a/src/cascadia/TerminalApp/AppLogic.idl
+++ b/src/cascadia/TerminalApp/AppLogic.idl
@@ -47,6 +47,7 @@ namespace TerminalApp
         Windows.UI.Xaml.ElementTheme GetRequestedTheme();
         Microsoft.Terminal.Settings.Model.LaunchMode GetLaunchMode();
         Boolean GetShowTabsInTitlebar();
+        Boolean GetInitialAlwaysOnTop();
         Single CalcSnappedDimension(Boolean widthOrHeight, Single dimension);
         void TitlebarClicked();
         void WindowCloseButtonClicked();
diff --git a/src/cascadia/TerminalApp/TerminalPage.cpp b/src/cascadia/TerminalApp/TerminalPage.cpp
index aa5cef1847e..8c16c74cfdb 100644
--- a/src/cascadia/TerminalApp/TerminalPage.cpp
+++ b/src/cascadia/TerminalApp/TerminalPage.cpp
@@ -239,6 +239,8 @@ namespace winrt::TerminalApp::implementation
         //
         // _OnFirstLayout will remove this handler so it doesn't get called more than once.
         _layoutUpdatedRevoker = _tabContent.LayoutUpdated(winrt::auto_revoke, { this, &TerminalPage::_OnFirstLayout });
+
+        _isAlwaysOnTop = _settings.GlobalSettings().AlwaysOnTop();
     }
 
     // Method Description:
diff --git a/src/cascadia/WindowsTerminal/AppHost.cpp b/src/cascadia/WindowsTerminal/AppHost.cpp
index d0b6a3aa734..5c258b6c59b 100644
--- a/src/cascadia/WindowsTerminal/AppHost.cpp
+++ b/src/cascadia/WindowsTerminal/AppHost.cpp
@@ -58,7 +58,7 @@ AppHost::AppHost() noexcept :
                                                 std::placeholders::_1,
                                                 std::placeholders::_2));
     _window->MouseScrolled({ this, &AppHost::_WindowMouseWheeled });
-    _window->SetAlwaysOnTop(_logic.AlwaysOnTop());
+    _window->SetAlwaysOnTop(_logic.GetInitialAlwaysOnTop());
     _window->MakeWindow();
 }