diff --git a/src/cascadia/TerminalApp/TerminalPage.cpp b/src/cascadia/TerminalApp/TerminalPage.cpp
index 678d70f2ae..7be3419840 100644
--- a/src/cascadia/TerminalApp/TerminalPage.cpp
+++ b/src/cascadia/TerminalApp/TerminalPage.cpp
@@ -1134,6 +1134,7 @@ namespace winrt::TerminalApp::implementation
 
             if (dispatchToElevatedWindow)
             {
+                newTerminalArgs.StartingDirectory(_evaluatePathForCwd(newTerminalArgs.StartingDirectory()));
                 _OpenElevatedWT(newTerminalArgs);
             }
             else
@@ -1174,6 +1175,23 @@ namespace winrt::TerminalApp::implementation
         }
     }
 
+    winrt::hstring TerminalPage::_evaluatePathForCwd(const winrt::hstring& path)
+    {
+        auto resultPath{ path };
+        const bool looksLikeLinux = resultPath.size() == 1 &&
+                                    (resultPath[0] == L'~' || resultPath[0] == L'/');
+        // if (newWorkingDirectory.size() == 0 || looksLikeLinux)
+        if (!looksLikeLinux)
+        { // We only want to resolve the new WD against the CWD if it doesn't look like a Linux path (see GH#592)
+            // auto cwdString{ wil::GetCurrentDirectoryW<std::wstring>() };
+            auto cwdString{ _WindowProperties.VirtualWorkingDirectory().c_str() };
+            std::filesystem::path cwd{ cwdString };
+            cwd /= path.c_str();
+            resultPath = winrt::hstring{ cwd.wstring() };
+        }
+        return resultPath;
+    }
+
     // Method Description:
     // - Creates a new connection based on the profile settings
     // Arguments:
@@ -1242,18 +1260,18 @@ namespace winrt::TerminalApp::implementation
             // construction, because the connection might not spawn the child
             // process until later, on another thread, after we've already
             // restored the CWD to its original value.
-            auto newWorkingDirectory{ settings.StartingDirectory() };
-            const bool looksLikeLinux = newWorkingDirectory.size() == 1 &&
-                                        (newWorkingDirectory[0] == L'~' || newWorkingDirectory[0] == L'/');
-            // if (newWorkingDirectory.size() == 0 || looksLikeLinux)
-            if (!looksLikeLinux)
-            { // We only want to resolve the new WD against the CWD if it doesn't look like a Linux path (see GH#592)
-                // auto cwdString{ wil::GetCurrentDirectoryW<std::wstring>() };
-                auto cwdString{ _WindowProperties.VirtualWorkingDirectory().c_str() };
-                std::filesystem::path cwd{ cwdString };
-                cwd /= settings.StartingDirectory().c_str();
-                newWorkingDirectory = winrt::hstring{ cwd.wstring() };
-            }
+            auto newWorkingDirectory{ _evaluatePathForCwd(settings.StartingDirectory()) };
+            // const bool looksLikeLinux = newWorkingDirectory.size() == 1 &&
+            //                             (newWorkingDirectory[0] == L'~' || newWorkingDirectory[0] == L'/');
+            // // if (newWorkingDirectory.size() == 0 || looksLikeLinux)
+            // if (!looksLikeLinux)
+            // { // We only want to resolve the new WD against the CWD if it doesn't look like a Linux path (see GH#592)
+            //     // auto cwdString{ wil::GetCurrentDirectoryW<std::wstring>() };
+            //     auto cwdString{ _WindowProperties.VirtualWorkingDirectory().c_str() };
+            //     std::filesystem::path cwd{ cwdString };
+            //     cwd /= settings.StartingDirectory().c_str();
+            //     newWorkingDirectory = winrt::hstring{ cwd.wstring() };
+            // }
 
             auto conhostConn = TerminalConnection::ConptyConnection();
             auto valueSet = TerminalConnection::ConptyConnection::CreateSettings(settings.Commandline(),
@@ -4273,6 +4291,9 @@ namespace winrt::TerminalApp::implementation
             // whatever the default profile's GUID is.
 
             newTerminalArgs.Profile(::Microsoft::Console::Utils::GuidToString(profile.Guid()));
+
+            newTerminalArgs.StartingDirectory(_evaluatePathForCwd(controlSettings.DefaultSettings().StartingDirectory()));
+
             _OpenElevatedWT(newTerminalArgs);
             return true;
         }
diff --git a/src/cascadia/TerminalApp/TerminalPage.h b/src/cascadia/TerminalApp/TerminalPage.h
index 95c291ee20..5f289fd0da 100644
--- a/src/cascadia/TerminalApp/TerminalPage.h
+++ b/src/cascadia/TerminalApp/TerminalPage.h
@@ -295,6 +295,9 @@ namespace winrt::TerminalApp::implementation
         void _OpenNewTabDropdown();
         HRESULT _OpenNewTab(const Microsoft::Terminal::Settings::Model::NewTerminalArgs& newTerminalArgs, winrt::Microsoft::Terminal::TerminalConnection::ITerminalConnection existingConnection = nullptr);
         void _CreateNewTabFromPane(std::shared_ptr<Pane> pane, uint32_t insertPosition = -1);
+
+        winrt::hstring _evaluatePathForCwd(const winrt::hstring& path);
+
         winrt::Microsoft::Terminal::TerminalConnection::ITerminalConnection _CreateConnectionFromSettings(Microsoft::Terminal::Settings::Model::Profile profile, Microsoft::Terminal::Settings::Model::TerminalSettings settings, const bool inheritCursor);
         winrt::Microsoft::Terminal::TerminalConnection::ITerminalConnection _duplicateConnectionForRestart(std::shared_ptr<Pane> pane);
         void _restartPaneConnection(const std::shared_ptr<Pane>& pane);