diff --git a/src/cascadia/PublicTerminalCore/HwndTerminal.cpp b/src/cascadia/PublicTerminalCore/HwndTerminal.cpp
index 79bebbe1705..e4d22a3bed1 100644
--- a/src/cascadia/PublicTerminalCore/HwndTerminal.cpp
+++ b/src/cascadia/PublicTerminalCore/HwndTerminal.cpp
@@ -559,7 +559,7 @@ void HwndTerminal::_SendKeyEvent(WORD vkey, WORD scanCode) noexcept
 try
 {
     const auto flags = getControlKeyState();
-    _terminal->SendKeyEvent(vkey, scanCode, flags);
+    _terminal->SendKeyEvent(vkey, scanCode, flags, true);
 }
 CATCH_LOG();
 
diff --git a/src/cascadia/TerminalControl/TermControl.cpp b/src/cascadia/TerminalControl/TermControl.cpp
index 62be8967f74..ccd096f29e7 100644
--- a/src/cascadia/TerminalControl/TermControl.cpp
+++ b/src/cascadia/TerminalControl/TermControl.cpp
@@ -712,7 +712,7 @@ namespace winrt::Microsoft::Terminal::TerminalControl::implementation
         if (!handled)
         {
             // _TrySendKeyEvent pretends it didn't handle F7 for some unknown reason.
-            (void)_TrySendKeyEvent(VK_F7, 0, modifiers);
+            (void)_TrySendKeyEvent(VK_F7, 0, modifiers, true);
             handled = true;
         }
 
@@ -721,6 +721,17 @@ namespace winrt::Microsoft::Terminal::TerminalControl::implementation
 
     void TermControl::_KeyDownHandler(winrt::Windows::Foundation::IInspectable const& /*sender*/,
                                       Input::KeyRoutedEventArgs const& e)
+    {
+        _KeyHandler(e, true);
+    }
+
+    void TermControl::_KeyUpHandler(winrt::Windows::Foundation::IInspectable const& /*sender*/,
+                                    Input::KeyRoutedEventArgs const& e)
+    {
+        _KeyHandler(e, false);
+    }
+
+    void TermControl::_KeyHandler(Input::KeyRoutedEventArgs const& e, const bool keyDown)
     {
         // If the current focused element is a child element of searchbox,
         // we do not send this event up to terminal
@@ -734,9 +745,9 @@ namespace winrt::Microsoft::Terminal::TerminalControl::implementation
         //   - key modifier is pressed
         // NOTE: for key combos like CTRL + C, two events are fired (one for CTRL, one for 'C'). We care about the 'C' event and then check for key modifiers below.
         if (_closing ||
-            e.OriginalKey() == VirtualKey::Control ||
-            e.OriginalKey() == VirtualKey::Shift ||
-            e.OriginalKey() == VirtualKey::Menu ||
+            // e.OriginalKey() == VirtualKey::Control ||
+            // e.OriginalKey() == VirtualKey::Shift ||
+            // e.OriginalKey() == VirtualKey::Menu ||
             e.OriginalKey() == VirtualKey::LeftWindows ||
             e.OriginalKey() == VirtualKey::RightWindows)
 
@@ -778,7 +789,7 @@ namespace winrt::Microsoft::Terminal::TerminalControl::implementation
 
         if (!handled)
         {
-            handled = _TrySendKeyEvent(vkey, scanCode, modifiers);
+            handled = _TrySendKeyEvent(vkey, scanCode, modifiers, keyDown);
         }
 
         // Manually prevent keyboard navigation with tab. We want to send tab to
@@ -800,7 +811,7 @@ namespace winrt::Microsoft::Terminal::TerminalControl::implementation
     // Arguments:
     // - vkey: The vkey of the key pressed.
     // - states: The Microsoft::Terminal::Core::ControlKeyStates representing the modifier key states.
-    bool TermControl::_TrySendKeyEvent(const WORD vkey, const WORD scanCode, const ControlKeyStates modifiers)
+    bool TermControl::_TrySendKeyEvent(const WORD vkey, const WORD scanCode, const ControlKeyStates modifiers, const bool keyDown)
     {
         // When there is a selection active, escape should clear it and NOT flow through
         // to the terminal. With any other keypress, it should clear the selection AND
@@ -825,7 +836,7 @@ namespace winrt::Microsoft::Terminal::TerminalControl::implementation
         // If the terminal translated the key, mark the event as handled.
         // This will prevent the system from trying to get the character out
         // of it and sending us a CharacterReceived event.
-        const auto handled = vkey ? _terminal->SendKeyEvent(vkey, scanCode, modifiers) : true;
+        const auto handled = vkey ? _terminal->SendKeyEvent(vkey, scanCode, modifiers, keyDown) : true;
 
         if (_cursorTimer.has_value())
         {
diff --git a/src/cascadia/TerminalControl/TermControl.h b/src/cascadia/TerminalControl/TermControl.h
index c42f2246abe..cb678d9ba83 100644
--- a/src/cascadia/TerminalControl/TermControl.h
+++ b/src/cascadia/TerminalControl/TermControl.h
@@ -180,6 +180,7 @@ namespace winrt::Microsoft::Terminal::TerminalControl::implementation
         void _SetFontSize(int fontSize);
         void _TappedHandler(Windows::Foundation::IInspectable const& sender, Windows::UI::Xaml::Input::TappedRoutedEventArgs const& e);
         void _KeyDownHandler(Windows::Foundation::IInspectable const& sender, Windows::UI::Xaml::Input::KeyRoutedEventArgs const& e);
+        void _KeyUpHandler(Windows::Foundation::IInspectable const& sender, Windows::UI::Xaml::Input::KeyRoutedEventArgs const& e);
         void _CharacterHandler(Windows::Foundation::IInspectable const& sender, Windows::UI::Xaml::Input::CharacterReceivedRoutedEventArgs const& e);
         void _PointerPressedHandler(Windows::Foundation::IInspectable const& sender, Windows::UI::Xaml::Input::PointerRoutedEventArgs const& e);
         void _PointerMovedHandler(Windows::Foundation::IInspectable const& sender, Windows::UI::Xaml::Input::PointerRoutedEventArgs const& e);
@@ -218,8 +219,9 @@ namespace winrt::Microsoft::Terminal::TerminalControl::implementation
         void _ScrollbarUpdater(Windows::UI::Xaml::Controls::Primitives::ScrollBar scrollbar, const int viewTop, const int viewHeight, const int bufferSize);
         static Windows::UI::Xaml::Thickness _ParseThicknessFromPadding(const hstring padding);
 
+        void _KeyHandler(Windows::UI::Xaml::Input::KeyRoutedEventArgs const& e, const bool keyDown);
         ::Microsoft::Terminal::Core::ControlKeyStates _GetPressedModifierKeys() const;
-        bool _TrySendKeyEvent(const WORD vkey, const WORD scanCode, ::Microsoft::Terminal::Core::ControlKeyStates modifiers);
+        bool _TrySendKeyEvent(const WORD vkey, const WORD scanCode, ::Microsoft::Terminal::Core::ControlKeyStates modifiers, const bool keyDown);
         bool _TrySendMouseEvent(Windows::UI::Input::PointerPoint const& point);
         bool _CanSendVTMouseInput();
 
diff --git a/src/cascadia/TerminalControl/TermControl.xaml b/src/cascadia/TerminalControl/TermControl.xaml
index 32609b73926..f39e4b1e9b8 100644
--- a/src/cascadia/TerminalControl/TermControl.xaml
+++ b/src/cascadia/TerminalControl/TermControl.xaml
@@ -19,6 +19,7 @@
     Tapped="_TappedHandler"
     PointerWheelChanged="_MouseWheelHandler"
     PreviewKeyDown="_KeyDownHandler"
+    KeyUp="_KeyUpHandler"
     CharacterReceived="_CharacterHandler"
     GotFocus="_GotFocusHandler"
     LostFocus="_LostFocusHandler">
diff --git a/src/cascadia/TerminalCore/ITerminalApi.hpp b/src/cascadia/TerminalCore/ITerminalApi.hpp
index b521f4ecea2..1e94e522e7c 100644
--- a/src/cascadia/TerminalCore/ITerminalApi.hpp
+++ b/src/cascadia/TerminalCore/ITerminalApi.hpp
@@ -47,6 +47,7 @@ namespace Microsoft::Terminal::Core
         virtual bool SetDefaultForeground(const DWORD color) noexcept = 0;
         virtual bool SetDefaultBackground(const DWORD color) noexcept = 0;
 
+        virtual bool EnableWin32InputMode(const bool win32InputMode) noexcept = 0;
         virtual bool SetCursorKeysMode(const bool applicationMode) noexcept = 0;
         virtual bool SetKeypadMode(const bool applicationMode) noexcept = 0;
         virtual bool EnableVT200MouseMode(const bool enabled) noexcept = 0;
diff --git a/src/cascadia/TerminalCore/ITerminalInput.hpp b/src/cascadia/TerminalCore/ITerminalInput.hpp
index 5df7a0845d3..1d9785e4ee6 100644
--- a/src/cascadia/TerminalCore/ITerminalInput.hpp
+++ b/src/cascadia/TerminalCore/ITerminalInput.hpp
@@ -16,7 +16,7 @@ namespace Microsoft::Terminal::Core
         ITerminalInput& operator=(const ITerminalInput&) = default;
         ITerminalInput& operator=(ITerminalInput&&) = default;
 
-        virtual bool SendKeyEvent(const WORD vkey, const WORD scanCode, const ControlKeyStates states) = 0;
+        virtual bool SendKeyEvent(const WORD vkey, const WORD scanCode, const ControlKeyStates states, const bool keyDown) = 0;
         virtual bool SendMouseEvent(const COORD viewportPos, const unsigned int uiButton, const ControlKeyStates states, const short wheelDelta) = 0;
         virtual bool SendCharEvent(const wchar_t ch, const WORD scanCode, const ControlKeyStates states) = 0;
 
diff --git a/src/cascadia/TerminalCore/Terminal.cpp b/src/cascadia/TerminalCore/Terminal.cpp
index 025d2abc7be..e9f81b64566 100644
--- a/src/cascadia/TerminalCore/Terminal.cpp
+++ b/src/cascadia/TerminalCore/Terminal.cpp
@@ -413,7 +413,7 @@ bool Terminal::IsTrackingMouseInput() const noexcept
 // Return Value:
 // - true if we translated the key event, and it should not be processed any further.
 // - false if we did not translate the key, and it should be processed into a character.
-bool Terminal::SendKeyEvent(const WORD vkey, const WORD scanCode, const ControlKeyStates states)
+bool Terminal::SendKeyEvent(const WORD vkey, const WORD scanCode, const ControlKeyStates states, const bool keyDown)
 {
     TrySnapOnInput();
     _StoreKeyEvent(vkey, scanCode);
@@ -443,7 +443,7 @@ bool Terminal::SendKeyEvent(const WORD vkey, const WORD scanCode, const ControlK
         return false;
     }
 
-    KeyEvent keyEv{ true, 0, vkey, scanCode, ch, states.Value() };
+    KeyEvent keyEv{ keyDown, 1, vkey, scanCode, ch, states.Value() };
     return _terminalInput->HandleKey(&keyEv);
 }
 
diff --git a/src/cascadia/TerminalCore/Terminal.hpp b/src/cascadia/TerminalCore/Terminal.hpp
index 8655987ae33..6f941a5527e 100644
--- a/src/cascadia/TerminalCore/Terminal.hpp
+++ b/src/cascadia/TerminalCore/Terminal.hpp
@@ -101,6 +101,7 @@ class Microsoft::Terminal::Core::Terminal final :
     bool SetDefaultForeground(const COLORREF color) noexcept override;
     bool SetDefaultBackground(const COLORREF color) noexcept override;
 
+    bool EnableWin32InputMode(const bool win32InputMode) noexcept override;
     bool SetCursorKeysMode(const bool applicationMode) noexcept override;
     bool SetKeypadMode(const bool applicationMode) noexcept override;
     bool EnableVT200MouseMode(const bool enabled) noexcept override;
@@ -115,7 +116,7 @@ class Microsoft::Terminal::Core::Terminal final :
 
 #pragma region ITerminalInput
     // These methods are defined in Terminal.cpp
-    bool SendKeyEvent(const WORD vkey, const WORD scanCode, const Microsoft::Terminal::Core::ControlKeyStates states) override;
+    bool SendKeyEvent(const WORD vkey, const WORD scanCode, const Microsoft::Terminal::Core::ControlKeyStates states, const bool keyDown) override;
     bool SendMouseEvent(const COORD viewportPos, const unsigned int uiButton, const ControlKeyStates states, const short wheelDelta) override;
     bool SendCharEvent(const wchar_t ch, const WORD scanCode, const ControlKeyStates states) override;
 
diff --git a/src/cascadia/TerminalCore/TerminalApi.cpp b/src/cascadia/TerminalCore/TerminalApi.cpp
index 4189e07b1d0..453d9c711cc 100644
--- a/src/cascadia/TerminalCore/TerminalApi.cpp
+++ b/src/cascadia/TerminalCore/TerminalApi.cpp
@@ -505,6 +505,12 @@ try
 }
 CATCH_LOG_RETURN_FALSE()
 
+bool Terminal::EnableWin32InputMode(const bool win32InputMode) noexcept
+{
+    _terminalInput->ChangeWin32InputMode(win32InputMode);
+    return true;
+}
+
 bool Terminal::SetCursorKeysMode(const bool applicationMode) noexcept
 {
     _terminalInput->ChangeCursorKeysMode(applicationMode);
diff --git a/src/cascadia/TerminalCore/TerminalDispatch.cpp b/src/cascadia/TerminalCore/TerminalDispatch.cpp
index c209e810d25..def069cbd2e 100644
--- a/src/cascadia/TerminalCore/TerminalDispatch.cpp
+++ b/src/cascadia/TerminalCore/TerminalDispatch.cpp
@@ -246,6 +246,18 @@ bool TerminalDispatch::SetCursorKeysMode(const bool applicationMode) noexcept
     return true;
 }
 
+// Method Description
+// - TODO
+// Arguments:
+// - applicationMode - set to true to enable Application Mode Input, false for Numeric Mode Input.
+// Return Value:
+// - True if handled successfully. False otherwise.
+bool TerminalDispatch::EnableWin32InputMode(const bool win32Mode) noexcept
+{
+    _terminalApi.EnableWin32InputMode(win32Mode);
+    return true;
+}
+
 //Routine Description:
 // Enable VT200 Mouse Mode - Enables/disables the mouse input handler in default tracking mode.
 //Arguments:
diff --git a/src/cascadia/TerminalCore/TerminalDispatch.hpp b/src/cascadia/TerminalCore/TerminalDispatch.hpp
index e3be6ecbe92..4defa9f4cfb 100644
--- a/src/cascadia/TerminalCore/TerminalDispatch.hpp
+++ b/src/cascadia/TerminalCore/TerminalDispatch.hpp
@@ -18,6 +18,8 @@ class TerminalDispatch : public Microsoft::Console::VirtualTerminal::TermDispatc
     bool CursorPosition(const size_t line,
                         const size_t column) noexcept override; // CUP
 
+    bool EnableWin32InputMode(const bool win32InputMode) noexcept override; // win32-input-mode
+
     bool CursorVisibility(const bool isVisible) noexcept override; // DECTCEM
     bool EnableCursorBlinking(const bool enable) noexcept override; // ATT610