diff --git a/src/cascadia/TerminalApp/TerminalPage.cpp b/src/cascadia/TerminalApp/TerminalPage.cpp
index 09cc175d693..653ae691594 100644
--- a/src/cascadia/TerminalApp/TerminalPage.cpp
+++ b/src/cascadia/TerminalApp/TerminalPage.cpp
@@ -837,13 +837,19 @@ 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 it's original value.
-            std::wstring cwdString{ wil::GetCurrentDirectoryW<std::wstring>() };
-            std::filesystem::path cwd{ cwdString };
-            cwd /= settings.StartingDirectory().c_str();
+            winrt::hstring newWorkingDirectory{ settings.StartingDirectory() };
+            if (newWorkingDirectory.size() <= 1 ||
+                !(newWorkingDirectory[0] == L'~' || newWorkingDirectory[0] == L'/'))
+            { // We only want to resolve the new WD against the CWD if it doesn't look like a Linux path (see GH#592)
+                std::wstring cwdString{ wil::GetCurrentDirectoryW<std::wstring>() };
+                std::filesystem::path cwd{ cwdString };
+                cwd /= settings.StartingDirectory().c_str();
+                newWorkingDirectory = winrt::hstring{ cwd.wstring() };
+            }
 
             auto conhostConn = TerminalConnection::ConptyConnection();
             conhostConn.Initialize(TerminalConnection::ConptyConnection::CreateSettings(settings.Commandline(),
-                                                                                        winrt::hstring{ cwd.wstring() },
+                                                                                        newWorkingDirectory,
                                                                                         settings.StartingTitle(),
                                                                                         envMap.GetView(),
                                                                                         ::base::saturated_cast<uint32_t>(settings.InitialRows()),
diff --git a/src/cascadia/TerminalConnection/ConptyConnection.cpp b/src/cascadia/TerminalConnection/ConptyConnection.cpp
index 1589f708d55..d82b6be0a4f 100644
--- a/src/cascadia/TerminalConnection/ConptyConnection.cpp
+++ b/src/cascadia/TerminalConnection/ConptyConnection.cpp
@@ -57,6 +57,72 @@ namespace winrt::Microsoft::Terminal::TerminalConnection::implementation
         return S_OK;
     }
 
+    // Function Description:
+    // - Promotes a starting directory provided to a WSL invocation to a commandline argument.
+    //   This is necessary because WSL has some modicum of support for linux-side directories (!) which
+    //   CreateProcess never will.
+    static std::tuple<std::wstring, std::wstring> _tryMangleStartingDirectoryForWSL(std::wstring_view commandLine, std::wstring_view startingDirectory)
+    {
+        do
+        {
+            if (startingDirectory.size() > 0 && commandLine.size() >= 3)
+            { // "wsl" is three characters; this is a safe bet. no point in doing it if there's no starting directory though!
+                // Find the first space, quote or the end of the string -- we'll look for wsl before that.
+                const auto terminator{ commandLine.find_first_of(LR"(" )", 1) }; // look past the first character in case it starts with "
+                const auto start{ til::at(commandLine, 0) == L'"' ? 1 : 0 };
+                const std::filesystem::path executablePath{ commandLine.substr(start, terminator - start) };
+                const auto executableFilename{ executablePath.filename().wstring() };
+                if (executableFilename == L"wsl" || executableFilename == L"wsl.exe")
+                {
+                    // We've got a WSL -- let's just make sure it's the right one.
+                    if (executablePath.has_parent_path())
+                    {
+                        std::wstring systemDirectory{};
+                        if (FAILED(wil::GetSystemDirectoryW(systemDirectory)))
+                        {
+                            break; // just bail out.
+                        }
+                        if (executablePath.parent_path().wstring() != systemDirectory)
+                        {
+                            break; // it wasn't in system32!
+                        }
+                    }
+                    else
+                    {
+                        // assume that unqualified WSL is the one in system32 (minor danger)
+                    }
+
+                    const auto arguments{ terminator == std::wstring_view::npos ? std::wstring_view{} : commandLine.substr(terminator + 1) };
+                    if (arguments.find(L"--cd") != std::wstring_view::npos)
+                    {
+                        break; // they've already got a --cd!
+                    }
+
+                    const auto tilde{ arguments.find_first_of(L'~') };
+                    if (tilde != std::wstring_view::npos)
+                    {
+                        if (tilde + 1 == arguments.size() || til::at(arguments, tilde + 1) == L' ')
+                        {
+                            // We want to suppress --cd if they have added a bare ~ to their commandline (they conflict).
+                            break;
+                        }
+                        // Tilde followed by non-space should be okay (like, wsl -d Debian ~/blah.sh)
+                    }
+
+                    return {
+                        fmt::format(LR"("{}" --cd "{}" {})", executablePath.wstring(), startingDirectory, arguments),
+                        std::wstring{}
+                    };
+                }
+            }
+        } while (false);
+
+        return {
+            std::wstring{ commandLine },
+            std::wstring{ startingDirectory }
+        };
+    }
+
     // Function Description:
     // - launches the client application attached to the new pseudoconsole
     HRESULT ConptyConnection::_LaunchAttachedClient() noexcept
@@ -163,11 +229,12 @@ namespace winrt::Microsoft::Terminal::TerminalConnection::implementation
             siEx.StartupInfo.lpTitle = mutableTitle.data();
         }
 
-        const wchar_t* const startingDirectory = _startingDirectory.size() > 0 ? _startingDirectory.c_str() : nullptr;
+        auto [newCommandLine, newStartingDirectory] = _tryMangleStartingDirectoryForWSL(cmdline, _startingDirectory);
+        const wchar_t* const startingDirectory = newStartingDirectory.size() > 0 ? newStartingDirectory.c_str() : nullptr;
 
         RETURN_IF_WIN32_BOOL_FALSE(CreateProcessW(
             nullptr,
-            cmdline.data(),
+            newCommandLine.data(),
             nullptr, // lpProcessAttributes
             nullptr, // lpThreadAttributes
             false, // bInheritHandles
diff --git a/src/cascadia/TerminalSettingsModel/Profile.cpp b/src/cascadia/TerminalSettingsModel/Profile.cpp
index a684acc95ab..d90a65884d4 100644
--- a/src/cascadia/TerminalSettingsModel/Profile.cpp
+++ b/src/cascadia/TerminalSettingsModel/Profile.cpp
@@ -448,11 +448,6 @@ winrt::Microsoft::Terminal::Settings::Model::FontConfig Profile::FontInfo()
 // - the function returns an evaluated version of %userprofile% to avoid blocking the session from starting.
 std::wstring Profile::EvaluateStartingDirectory(const std::wstring& directory)
 {
-    // First expand path
-    DWORD numCharsInput = ExpandEnvironmentStrings(directory.c_str(), nullptr, 0);
-    std::unique_ptr<wchar_t[]> evaluatedPath = std::make_unique<wchar_t[]>(numCharsInput);
-    THROW_LAST_ERROR_IF(0 == ExpandEnvironmentStrings(directory.c_str(), evaluatedPath.get(), numCharsInput));
-
     // Prior to GH#9541, we'd validate that the user's startingDirectory existed
     // here. If it was invalid, we'd gracefully fall back to %USERPROFILE%.
     //
@@ -463,7 +458,7 @@ std::wstring Profile::EvaluateStartingDirectory(const std::wstring& directory)
     //
     // If the path is eventually invalid, we'll display warning in the
     // ConptyConnection when the process fails to launch.
-    return std::wstring(evaluatedPath.get(), numCharsInput);
+    return wil::ExpandEnvironmentStringsW<std::wstring>(directory.c_str());
 }
 
 // Function Description: