diff --git a/doc/cascadia/profiles.schema.json b/doc/cascadia/profiles.schema.json
index 391095c379f..2179a4c294f 100644
--- a/doc/cascadia/profiles.schema.json
+++ b/doc/cascadia/profiles.schema.json
@@ -350,6 +350,7 @@
         "switchToTab",
         "tabSearch",
         "toggleAlwaysOnTop",
+        "toggleBlockSelection",
         "toggleFocusMode",
         "selectAll",
         "setFocusMode",
diff --git a/src/cascadia/TerminalControl/ControlCore.cpp b/src/cascadia/TerminalControl/ControlCore.cpp
index 19d66932227..3472bf1016e 100644
--- a/src/cascadia/TerminalControl/ControlCore.cpp
+++ b/src/cascadia/TerminalControl/ControlCore.cpp
@@ -417,11 +417,12 @@ namespace winrt::Microsoft::Terminal::Control::implementation
             vkey != VK_SNAPSHOT &&
             keyDown)
         {
-            if (_terminal->IsInMarkMode() && modifiers.IsCtrlPressed() && vkey == 'A')
+            const auto isInMarkMode = _terminal->SelectionMode() == ::Microsoft::Terminal::Core::Terminal::SelectionInteractionMode::Mark;
+            if (isInMarkMode && modifiers.IsCtrlPressed() && vkey == 'A')
             {
                 auto lock = _terminal->LockForWriting();
                 _terminal->SelectAll();
-                _updateSelection();
+                _updateSelectionUI();
                 return true;
             }
 
@@ -430,7 +431,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
             {
                 auto lock = _terminal->LockForWriting();
                 _terminal->UpdateSelection(updateSlnParams->first, updateSlnParams->second, modifiers);
-                _updateSelection();
+                _updateSelectionUI();
                 return true;
             }
 
@@ -438,7 +439,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
             if (!modifiers.IsWinPressed())
             {
                 _terminal->ClearSelection();
-                _updateSelection();
+                _updateSelectionUI();
             }
 
             // When there is a selection active, escape should clear it and NOT flow through
@@ -950,8 +951,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         const auto end{ _terminal->SelectionEndForRendering() };
         info.EndPos = { end.X, end.Y };
 
-        info.MovingEnd = _terminal->MovingEnd();
-        info.MovingCursor = _terminal->MovingCursor();
+        info.Endpoint = static_cast<SelectionEndpointTarget>(_terminal->SelectionEndpointTarget());
 
         const auto bufferSize{ _terminal->GetTextBuffer().GetSize() };
         info.StartAtLeftBoundary = _terminal->GetSelectionAnchor().x == bufferSize.Left();
@@ -981,11 +981,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
 
         // save location (for rendering) + render
         _terminal->SetSelectionEnd(terminalPosition);
-        _renderer->TriggerSelection();
-
-        // this is used for mouse dragging,
-        // so hide the markers
-        _UpdateSelectionMarkersHandlers(*this, winrt::make<implementation::UpdateSelectionMarkersEventArgs>(true));
+        _updateSelectionUI();
     }
 
     // Called when the Terminal wants to set something to the clipboard, i.e.
@@ -998,7 +994,6 @@ namespace winrt::Microsoft::Terminal::Control::implementation
     // Method Description:
     // - Given a copy-able selection, get the selected text from the buffer and send it to the
     //     Windows Clipboard (CascadiaWin32:main.cpp).
-    // - CopyOnSelect does NOT clear the selection
     // Arguments:
     // - singleLine: collapse all of the text to one line
     // - formats: which formats to copy (defined by action's CopyFormatting arg). nullptr
@@ -1044,12 +1039,6 @@ namespace winrt::Microsoft::Terminal::Control::implementation
                                                     bgColor) :
                                  "";
 
-        if (!_settings->CopyOnSelect())
-        {
-            _terminal->ClearSelection();
-            _updateSelection();
-        }
-
         // send data up for clipboard
         _CopyToClipboardHandlers(*this,
                                  winrt::make<CopyToClipboardEventArgs>(winrt::hstring{ textData },
@@ -1063,7 +1052,14 @@ namespace winrt::Microsoft::Terminal::Control::implementation
     {
         auto lock = _terminal->LockForWriting();
         _terminal->SelectAll();
-        _updateSelection();
+        _updateSelectionUI();
+    }
+
+    void ControlCore::ClearSelection()
+    {
+        auto lock = _terminal->LockForWriting();
+        _terminal->ClearSelection();
+        _updateSelectionUI();
     }
 
     bool ControlCore::ToggleBlockSelection()
@@ -1085,12 +1081,12 @@ namespace winrt::Microsoft::Terminal::Control::implementation
     {
         auto lock = _terminal->LockForWriting();
         _terminal->ToggleMarkMode();
-        _updateSelection();
+        _updateSelectionUI();
     }
 
-    bool ControlCore::IsInMarkMode() const
+    Control::SelectionInteractionMode ControlCore::SelectionMode() const
     {
-        return _terminal->IsInMarkMode();
+        return static_cast<Control::SelectionInteractionMode>(_terminal->SelectionMode());
     }
 
     // Method Description:
@@ -1100,7 +1096,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
     {
         _terminal->WritePastedText(hstr);
         _terminal->ClearSelection();
-        _updateSelection();
+        _updateSelectionUI();
         _terminal->TrySnapOnInput();
     }
 
@@ -1420,10 +1416,11 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         {
             _terminal->SetBlockSelection(false);
             search.Select();
-            _renderer->TriggerSelection();
 
             // this is used for search,
-            // so hide the markers
+            // DO NOT call _updateSelectionUI() here.
+            // We don't want to show the markers so manually tell it to clear it.
+            _renderer->TriggerSelection();
             _UpdateSelectionMarkersHandlers(*this, winrt::make<implementation::UpdateSelectionMarkersEventArgs>(true));
         }
 
@@ -1625,14 +1622,17 @@ namespace winrt::Microsoft::Terminal::Control::implementation
             _terminal->MultiClickSelection(terminalPosition, mode);
             selectionNeedsToBeCopied = true;
         }
-        _updateSelection();
+        _updateSelectionUI();
     }
 
-    void ControlCore::_updateSelection()
+    // Method Description:
+    // - Updates the renderer's representation of the selection as well as the selection marker overlay in TermControl
+    void ControlCore::_updateSelectionUI()
     {
         _renderer->TriggerSelection();
-        const bool clearMarkers{ !_terminal->IsSelectionActive() };
-        _UpdateSelectionMarkersHandlers(*this, winrt::make<implementation::UpdateSelectionMarkersEventArgs>(clearMarkers));
+        // only show the markers if we're doing a keyboard selection or in mark mode
+        const bool showMarkers{ _terminal->SelectionMode() >= ::Microsoft::Terminal::Core::Terminal::SelectionInteractionMode::Keyboard };
+        _UpdateSelectionMarkersHandlers(*this, winrt::make<implementation::UpdateSelectionMarkersEventArgs>(!showMarkers));
     }
 
     void ControlCore::AttachUiaEngine(::Microsoft::Console::Render::IRenderEngine* const pEngine)
diff --git a/src/cascadia/TerminalControl/ControlCore.h b/src/cascadia/TerminalControl/ControlCore.h
index e11bd19772a..5f021c10a07 100644
--- a/src/cascadia/TerminalControl/ControlCore.h
+++ b/src/cascadia/TerminalControl/ControlCore.h
@@ -82,9 +82,10 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         void PasteText(const winrt::hstring& hstr);
         bool CopySelectionToClipboard(bool singleLine, const Windows::Foundation::IReference<CopyFormat>& formats);
         void SelectAll();
+        void ClearSelection();
         bool ToggleBlockSelection();
         void ToggleMarkMode();
-        bool IsInMarkMode() const;
+        Control::SelectionInteractionMode SelectionMode() const;
 
         void GotFocus();
         void LostFocus();
@@ -271,7 +272,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         bool _setFontSizeUnderLock(int fontSize);
         void _updateFont(const bool initialUpdate = false);
         void _refreshSizeUnderLock();
-        void _updateSelection();
+        void _updateSelectionUI();
 
         void _sendInputToConnection(std::wstring_view wstr);
 
diff --git a/src/cascadia/TerminalControl/ControlCore.idl b/src/cascadia/TerminalControl/ControlCore.idl
index 1dc39842f97..a1d348d8a26 100644
--- a/src/cascadia/TerminalControl/ControlCore.idl
+++ b/src/cascadia/TerminalControl/ControlCore.idl
@@ -29,12 +29,26 @@ namespace Microsoft.Terminal.Control
         All
     };
 
+    enum SelectionInteractionMode
+    {
+        None,
+        Mouse,
+        Keyboard,
+        Mark
+    };
+
+    [flags]
+    enum SelectionEndpointTarget
+    {
+        Start = 0x1,
+        End = 0x2
+    };
+
     struct SelectionData
     {
         Microsoft.Terminal.Core.Point StartPos;
         Microsoft.Terminal.Core.Point EndPos;
-        Boolean MovingEnd;
-        Boolean MovingCursor;
+        SelectionEndpointTarget Endpoint;
         Boolean StartAtLeftBoundary;
         Boolean EndAtRightBoundary;
     };
@@ -75,10 +89,10 @@ namespace Microsoft.Terminal.Control
         void SendInput(String text);
         void PasteText(String text);
         void SelectAll();
+        void ClearSelection();
         Boolean ToggleBlockSelection();
         void ToggleMarkMode();
         void ClearBuffer(ClearBufferType clearType);
-        Boolean IsInMarkMode();
 
         void SetHoveredCell(Microsoft.Terminal.Core.Point terminalPosition);
         void ClearHoveredCell();
@@ -101,6 +115,7 @@ namespace Microsoft.Terminal.Control
         Boolean HasSelection { get; };
         IVector<String> SelectedText(Boolean trimTrailingWhitespace);
         SelectionData SelectionInfo { get; };
+        SelectionInteractionMode SelectionMode();
 
         String HoveredUriText { get; };
         Windows.Foundation.IReference<Microsoft.Terminal.Core.Point> HoveredCell { get; };
diff --git a/src/cascadia/TerminalControl/ControlInteractivity.cpp b/src/cascadia/TerminalControl/ControlInteractivity.cpp
index 85f92cba396..75b8cf5b614 100644
--- a/src/cascadia/TerminalControl/ControlInteractivity.cpp
+++ b/src/cascadia/TerminalControl/ControlInteractivity.cpp
@@ -142,7 +142,6 @@ namespace winrt::Microsoft::Terminal::Control::implementation
     // Method Description:
     // - Given a copy-able selection, get the selected text from the buffer and send it to the
     //     Windows Clipboard (CascadiaWin32:main.cpp).
-    // - CopyOnSelect does NOT clear the selection
     // Arguments:
     // - singleLine: collapse all of the text to one line
     // - formats: which formats to copy (defined by action's CopyFormatting arg). nullptr
@@ -257,15 +256,15 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         }
         else if (WI_IsFlagSet(buttonState, MouseButtonState::IsRightButtonDown))
         {
-            // CopyOnSelect right click always pastes
-            if (_core->CopyOnSelect() || !_core->HasSelection())
+            // Try to copy the text and clear the selection
+            const auto successfulCopy = CopySelectionToClipboard(shiftEnabled, nullptr);
+            _core->ClearSelection();
+            if (_core->CopyOnSelect() || !successfulCopy)
             {
+                // CopyOnSelect: right click always pastes!
+                // Otherwise: no selection --> paste
                 RequestPasteTextFromClipboard();
             }
-            else
-            {
-                CopySelectionToClipboard(shiftEnabled, nullptr);
-            }
         }
     }
 
@@ -383,6 +382,9 @@ namespace winrt::Microsoft::Terminal::Control::implementation
             isLeftMouseRelease &&
             _selectionNeedsToBeCopied)
         {
+            // IMPORTANT!
+            // DO NOT clear the selection here!
+            // Otherwise, the selection will be cleared immediately after you make it.
             CopySelectionToClipboard(false, nullptr);
         }
 
diff --git a/src/cascadia/TerminalControl/TermControl.cpp b/src/cascadia/TerminalControl/TermControl.cpp
index fb44871fdd6..1e5dcdc9f1a 100644
--- a/src/cascadia/TerminalControl/TermControl.cpp
+++ b/src/cascadia/TerminalControl/TermControl.cpp
@@ -1188,7 +1188,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         {
             // Manually show the cursor when a key is pressed. Restarting
             // the timer prevents flickering.
-            _core.CursorOn(!_core.IsInMarkMode());
+            _core.CursorOn(_core.SelectionMode() != SelectionInteractionMode::Mark);
             _cursorTimer->Start();
         }
 
@@ -1659,7 +1659,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         if (_cursorTimer)
         {
             // When the terminal focuses, show the cursor immediately
-            _core.CursorOn(!_core.IsInMarkMode());
+            _core.CursorOn(_core.SelectionMode() != SelectionInteractionMode::Mark);
             _cursorTimer->Start();
         }
 
@@ -1902,7 +1902,9 @@ namespace winrt::Microsoft::Terminal::Control::implementation
             return false;
         }
 
-        return _interactivity.CopySelectionToClipboard(singleLine, formats);
+        const auto successfulCopy = _interactivity.CopySelectionToClipboard(singleLine, formats);
+        _core.ClearSelection();
+        return successfulCopy;
     }
 
     // Method Description:
@@ -2830,9 +2832,10 @@ namespace winrt::Microsoft::Terminal::Control::implementation
 
                 // show/update selection markers
                 // figure out which endpoint to move, get it and the relevant icon (hide the other icon)
-                const auto selectionAnchor{ markerData.MovingEnd ? markerData.EndPos : markerData.StartPos };
-                const auto& marker{ markerData.MovingEnd ? SelectionEndMarker() : SelectionStartMarker() };
-                const auto& otherMarker{ markerData.MovingEnd ? SelectionStartMarker() : SelectionEndMarker() };
+                const auto movingEnd{ WI_IsFlagSet(markerData.Endpoint, SelectionEndpointTarget::End) };
+                const auto selectionAnchor{ movingEnd ? markerData.EndPos : markerData.StartPos };
+                const auto& marker{ movingEnd ? SelectionEndMarker() : SelectionStartMarker() };
+                const auto& otherMarker{ movingEnd ? SelectionStartMarker() : SelectionEndMarker() };
                 if (selectionAnchor.Y < 0 || selectionAnchor.Y >= _core.ViewHeight())
                 {
                     // if the endpoint is outside of the viewport,
@@ -2841,7 +2844,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
                     otherMarker.Visibility(Visibility::Collapsed);
                     co_return;
                 }
-                else if (markerData.MovingCursor)
+                else if (WI_AreAllFlagsSet(markerData.Endpoint, SelectionEndpointTarget::Start | SelectionEndpointTarget::End))
                 {
                     // display both markers
                     displayMarker(true);
@@ -2851,7 +2854,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
                 {
                     // display one marker,
                     // but hide the other
-                    displayMarker(markerData.MovingEnd);
+                    displayMarker(movingEnd);
                     otherMarker.Visibility(Visibility::Collapsed);
                 }
             }
diff --git a/src/cascadia/TerminalCore/Terminal.cpp b/src/cascadia/TerminalCore/Terminal.cpp
index fe63670a6a5..2e78808f8e2 100644
--- a/src/cascadia/TerminalCore/Terminal.cpp
+++ b/src/cascadia/TerminalCore/Terminal.cpp
@@ -45,8 +45,9 @@ Terminal::Terminal() :
     _snapOnInput{ true },
     _altGrAliasing{ true },
     _blockSelection{ false },
-    _markMode{ false },
+    _selectionMode{ SelectionInteractionMode::None },
     _selection{ std::nullopt },
+    _selectionEndpoint{ static_cast<SelectionEndpoint>(0) },
     _taskbarState{ 0 },
     _taskbarProgress{ 0 },
     _trimBlockSelection{ false },
@@ -1369,7 +1370,7 @@ void Terminal::SetCursorOn(const bool isOn)
 bool Terminal::IsCursorBlinkingAllowed() const noexcept
 {
     const auto& cursor = _activeBuffer().GetCursor();
-    return !_markMode && cursor.IsBlinkingAllowed();
+    return _selectionMode != SelectionInteractionMode::Mark && cursor.IsBlinkingAllowed();
 }
 
 // Method Description:
diff --git a/src/cascadia/TerminalCore/Terminal.hpp b/src/cascadia/TerminalCore/Terminal.hpp
index 092dcf7c185..7f08390cbd2 100644
--- a/src/cascadia/TerminalCore/Terminal.hpp
+++ b/src/cascadia/TerminalCore/Terminal.hpp
@@ -233,6 +233,14 @@ class Microsoft::Terminal::Core::Terminal final :
 
 #pragma region TextSelection
     // These methods are defined in TerminalSelection.cpp
+    enum class SelectionInteractionMode
+    {
+        None,
+        Mouse,
+        Keyboard,
+        Mark
+    };
+
     enum class SelectionDirection
     {
         Left,
@@ -249,21 +257,27 @@ class Microsoft::Terminal::Core::Terminal final :
         Viewport,
         Buffer
     };
+
+    enum class SelectionEndpoint
+    {
+        Start = 0x1,
+        End = 0x2
+    };
+
     void MultiClickSelection(const til::point viewportPos, SelectionExpansion expansionMode);
     void SetSelectionAnchor(const til::point position);
     void SetSelectionEnd(const til::point position, std::optional<SelectionExpansion> newExpansionMode = std::nullopt);
     void SetBlockSelection(const bool isEnabled) noexcept;
     void UpdateSelection(SelectionDirection direction, SelectionExpansion mode, ControlKeyStates mods);
     void SelectAll();
-    bool IsInMarkMode() const;
+    SelectionInteractionMode SelectionMode() const noexcept;
     void ToggleMarkMode();
 
     using UpdateSelectionParams = std::optional<std::pair<SelectionDirection, SelectionExpansion>>;
     UpdateSelectionParams ConvertKeyEventToUpdateSelectionParams(const ControlKeyStates mods, const WORD vkey) const;
-    bool MovingEnd() const noexcept;
-    bool MovingCursor() const noexcept;
     til::point SelectionStartForRendering() const;
     til::point SelectionEndForRendering() const;
+    const SelectionEndpoint SelectionEndpointTarget() const noexcept;
 
     const TextBuffer::TextAndColor RetrieveSelectedTextFromBuffer(bool trimTrailingWhitespace);
 #pragma endregion
@@ -333,7 +347,8 @@ class Microsoft::Terminal::Core::Terminal final :
     bool _blockSelection;
     std::wstring _wordDelimiters;
     SelectionExpansion _multiClickSelectionMode;
-    bool _markMode;
+    SelectionInteractionMode _selectionMode;
+    SelectionEndpoint _selectionEndpoint;
 #pragma endregion
 
     std::unique_ptr<TextBuffer> _mainBuffer;
diff --git a/src/cascadia/TerminalCore/TerminalSelection.cpp b/src/cascadia/TerminalCore/TerminalSelection.cpp
index 4f2693560fa..6deddbd936d 100644
--- a/src/cascadia/TerminalCore/TerminalSelection.cpp
+++ b/src/cascadia/TerminalCore/TerminalSelection.cpp
@@ -7,6 +7,8 @@
 
 using namespace Microsoft::Terminal::Core;
 
+DEFINE_ENUM_FLAG_OPERATORS(Terminal::SelectionEndpoint);
+
 /* Selection Pivot Description:
  *   The pivot helps properly update the selection when a user moves a selection over itself
  *   See SelectionTest::DoubleClickDrag_Left for an example of the functionality mentioned here
@@ -120,6 +122,11 @@ til::point Terminal::SelectionEndForRendering() const
     return til::point{ pos };
 }
 
+const Terminal::SelectionEndpoint Terminal::SelectionEndpointTarget() const noexcept
+{
+    return _selectionEndpoint;
+}
+
 // Method Description:
 // - Checks if selection is active
 // Return Value:
@@ -208,6 +215,7 @@ void Terminal::SetSelectionEnd(const til::point viewportPos, std::optional<Selec
         // expand both anchors
         std::tie(_selection->start, _selection->end) = expandedAnchors;
     }
+    _selectionMode = SelectionInteractionMode::Mouse;
 }
 
 // Method Description:
@@ -273,14 +281,14 @@ void Terminal::SetBlockSelection(const bool isEnabled) noexcept
     _blockSelection = isEnabled;
 }
 
-bool Terminal::IsInMarkMode() const
+Terminal::SelectionInteractionMode Terminal::SelectionMode() const noexcept
 {
-    return _markMode;
+    return _selectionMode;
 }
 
 void Terminal::ToggleMarkMode()
 {
-    if (_markMode)
+    if (_selectionMode == SelectionInteractionMode::Mark)
     {
         // Exit Mark Mode
         ClearSelection();
@@ -295,14 +303,15 @@ void Terminal::ToggleMarkMode()
         _selection->start = cursorPos;
         _selection->end = cursorPos;
         _selection->pivot = cursorPos;
-        _markMode = true;
+        _selectionMode = SelectionInteractionMode::Mark;
         _blockSelection = false;
+        WI_SetAllFlags(_selectionEndpoint, SelectionEndpoint::Start | SelectionEndpoint::End);
     }
 }
 
 Terminal::UpdateSelectionParams Terminal::ConvertKeyEventToUpdateSelectionParams(const ControlKeyStates mods, const WORD vkey) const
 {
-    if ((_markMode || mods.IsShiftPressed()) && !mods.IsAltPressed())
+    if ((_selectionMode == SelectionInteractionMode::Mark || mods.IsShiftPressed()) && !mods.IsAltPressed())
     {
         if (mods.IsCtrlPressed())
         {
@@ -348,21 +357,6 @@ Terminal::UpdateSelectionParams Terminal::ConvertKeyEventToUpdateSelectionParams
     return std::nullopt;
 }
 
-bool Terminal::MovingEnd() const noexcept
-{
-    // true --> we're moving end endpoint ("lower")
-    // false --> we're moving start endpoint ("higher")
-    return _selection->start == _selection->pivot;
-}
-
-bool Terminal::MovingCursor() const noexcept
-{
-    // Relevant for keyboard selection:
-    // true --> the selection is just a "cursor"; we're moving everything together with arrow keys
-    // false --> otherwise
-    return _selection->start == _selection->pivot && _selection->pivot == _selection->end;
-}
-
 // Method Description:
 // - updates the selection endpoints based on a direction and expansion mode. Primarily used for keyboard selection.
 // Arguments:
@@ -372,11 +366,27 @@ bool Terminal::MovingCursor() const noexcept
 void Terminal::UpdateSelection(SelectionDirection direction, SelectionExpansion mode, ControlKeyStates mods)
 {
     // 1. Figure out which endpoint to update
-    // One of the endpoints is the pivot,
-    // signifying that the other endpoint is the one we want to move.
-    auto targetPos{ MovingEnd() ? _selection->end : _selection->start };
+    // [Mark Mode]
+    // - shift pressed --> only move "end" (or "start" if "pivot" == "end")
+    // - otherwise --> move both "start" and "end" (moving cursor)
+    // [Quick Edit]
+    // - just move "end" (or "start" if "pivot" == "end")
+    _selectionEndpoint = static_cast<SelectionEndpoint>(0);
+    if (_selectionMode == SelectionInteractionMode::Mark && !mods.IsShiftPressed())
+    {
+        WI_SetAllFlags(_selectionEndpoint, SelectionEndpoint::Start | SelectionEndpoint::End);
+    }
+    else if (_selection->start == _selection->pivot)
+    {
+        WI_SetFlag(_selectionEndpoint, SelectionEndpoint::End);
+    }
+    else if (_selection->end == _selection->pivot)
+    {
+        WI_SetFlag(_selectionEndpoint, SelectionEndpoint::Start);
+    }
+    auto targetPos{ WI_IsFlagSet(_selectionEndpoint, SelectionEndpoint::Start) ? _selection->start : _selection->end };
 
-    // 2.A) Perform the movement
+    // 2 Perform the movement
     switch (mode)
     {
     case SelectionExpansion::Char:
@@ -393,11 +403,9 @@ void Terminal::UpdateSelection(SelectionDirection direction, SelectionExpansion
         break;
     }
 
-    // 2.B) Clamp the movement to the mutable viewport
-    targetPos = std::min(targetPos, _GetMutableViewport().BottomRightInclusive());
-
-    // 3. Actually modify the selection
-    if (_markMode && !mods.IsShiftPressed())
+    // 3. Actually modify the selection state
+    _selectionMode = std::max(_selectionMode, SelectionInteractionMode::Keyboard);
+    if (_selectionMode == SelectionInteractionMode::Mark && !mods.IsShiftPressed())
     {
         // [Mark Mode] + shift unpressed --> move all three (i.e. just use arrow keys)
         _selection->start = targetPos;
@@ -407,9 +415,14 @@ void Terminal::UpdateSelection(SelectionDirection direction, SelectionExpansion
     else
     {
         // [Mark Mode] + shift --> updating a standard selection
-        // NOTE: targetStart doesn't matter here
-        auto targetStart = false;
+        // This is also standard quick-edit modification
+        bool targetStart = false;
         std::tie(_selection->start, _selection->end) = _PivotSelection(targetPos, targetStart);
+
+        // IMPORTANT! Pivoting the selection here might have changed which endpoint we're targeting.
+        // So let's set the targeted endpoint again.
+        WI_UpdateFlag(_selectionEndpoint, SelectionEndpoint::Start, targetStart);
+        WI_UpdateFlag(_selectionEndpoint, SelectionEndpoint::End, !targetStart);
     }
 
     // 4. Scroll (if necessary)
@@ -438,6 +451,7 @@ void Terminal::SelectAll()
     _selection->start = bufferSize.Origin();
     _selection->end = { bufferSize.RightInclusive(), _GetMutableViewport().BottomInclusive() };
     _selection->pivot = _selection->end;
+    _selectionMode = SelectionInteractionMode::Keyboard;
 }
 
 void Terminal::_MoveByChar(SelectionDirection direction, til::point& pos)
@@ -455,13 +469,16 @@ void Terminal::_MoveByChar(SelectionDirection direction, til::point& pos)
     case SelectionDirection::Up:
     {
         const auto bufferSize{ _activeBuffer().GetSize() };
-        pos = { pos.X, std::clamp(pos.Y - 1, bufferSize.Top(), bufferSize.BottomInclusive()) };
+        const auto newY{ pos.Y - 1 };
+        pos = newY < bufferSize.Top() ? bufferSize.Origin() : til::point{ pos.X, newY };
         break;
     }
     case SelectionDirection::Down:
     {
         const auto bufferSize{ _activeBuffer().GetSize() };
-        pos = { pos.X, std::clamp(pos.Y + 1, bufferSize.Top(), bufferSize.BottomInclusive()) };
+        const auto mutableBottom{ _GetMutableViewport().BottomInclusive() };
+        const auto newY{ pos.Y + 1 };
+        pos = newY > mutableBottom ? til::point{ bufferSize.RightInclusive(), mutableBottom } : til::point{ pos.X, newY };
         break;
     }
     }
@@ -579,7 +596,8 @@ void Terminal::_MoveByBuffer(SelectionDirection direction, til::point& pos)
 void Terminal::ClearSelection()
 {
     _selection = std::nullopt;
-    _markMode = false;
+    _selectionMode = SelectionInteractionMode::None;
+    _selectionEndpoint = static_cast<SelectionEndpoint>(0);
 }
 
 // Method Description:
diff --git a/src/cascadia/TerminalSettingsModel/defaults.json b/src/cascadia/TerminalSettingsModel/defaults.json
index e6d68bb2af1..6067aa6130e 100644
--- a/src/cascadia/TerminalSettingsModel/defaults.json
+++ b/src/cascadia/TerminalSettingsModel/defaults.json
@@ -382,6 +382,7 @@
         // Clipboard Integration
         { "command": { "action": "copy", "singleLine": false }, "keys": "ctrl+shift+c" },
         { "command": { "action": "copy", "singleLine": false }, "keys": "ctrl+insert" },
+        { "command": { "action": "copy", "singleLine": false }, "keys": "enter" },
         { "command": "paste", "keys": "ctrl+shift+v" },
         { "command": "paste", "keys": "shift+insert" },
         { "command": "selectAll", "keys": "ctrl+shift+a" },