diff --git a/src/cascadia/TerminalControl/ControlInteractivity.cpp b/src/cascadia/TerminalControl/ControlInteractivity.cpp
index 7eaf4275535..8521d6e835c 100644
--- a/src/cascadia/TerminalControl/ControlInteractivity.cpp
+++ b/src/cascadia/TerminalControl/ControlInteractivity.cpp
@@ -255,10 +255,21 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         }
         else if (WI_IsFlagSet(buttonState, MouseButtonState::IsRightButtonDown))
         {
-            // Try to copy the text and clear the selection
-            const auto successfulCopy = CopySelectionToClipboard(shiftEnabled, nullptr);
+            const auto copyOnSelect{ _core->CopyOnSelect() };
+            bool successfulCopy = false;
+
+            // Don't try to copy if we're in copyOnSelect mode and have already
+            // copied this selection. GH#14464 demonstrates a scenario where the
+            // buffer contents might have changed since the selection was made,
+            // and copying here would cause weirdness.
+            if (_selectionNeedsToBeCopied || !copyOnSelect)
+            {
+                // Try to copy the text and clear the selection
+                successfulCopy = CopySelectionToClipboard(shiftEnabled, nullptr);
+            }
             _core->ClearSelection();
-            if (_core->CopyOnSelect() || !successfulCopy)
+
+            if (copyOnSelect || !successfulCopy)
             {
                 // CopyOnSelect: right click always pastes!
                 // Otherwise: no selection --> paste
diff --git a/src/cascadia/UnitTests_Control/ControlInteractivityTests.cpp b/src/cascadia/UnitTests_Control/ControlInteractivityTests.cpp
index 5a1225d8335..f9b018f4d62 100644
--- a/src/cascadia/UnitTests_Control/ControlInteractivityTests.cpp
+++ b/src/cascadia/UnitTests_Control/ControlInteractivityTests.cpp
@@ -43,6 +43,9 @@ namespace ControlUnitTests
         TEST_METHOD(GetMouseEventsInTest);
         TEST_METHOD(AltBufferClampMouse);
 
+        TEST_METHOD(CopyOnSelectSimple);
+        TEST_METHOD(CopyOnSelectAltBuffer);
+
         TEST_CLASS_SETUP(ClassSetup)
         {
             winrt::init_apartment(winrt::apartment_type::single_threaded);
@@ -966,4 +969,183 @@ namespace ControlUnitTests
                                       cursorPosition1.to_core_point());
         VERIFY_ARE_EQUAL(0u, expectedOutput.size(), L"Validate we drained all the expected output");
     }
+
+    void ControlInteractivityTests::CopyOnSelectSimple()
+    {
+        auto [settings, conn] = _createSettingsAndConnection();
+        settings->CopyOnSelect(true);
+        auto [core, interactivity] = _createCoreAndInteractivity(*settings, *conn);
+        _standardInit(core, interactivity);
+        auto& term{ *core->_terminal };
+
+        // Output some text
+        for (auto i = 0; i < core->ViewHeight() / 2; ++i)
+        {
+            conn->WriteInput(winrt::hstring{ fmt::format(L"line {}\r\n", i) });
+        }
+
+        // A callback for checking Copy events. expectedCopyContents=nullopt
+        // indicates that we're not expecting any copy events.
+        std::optional<std::wstring> expectedCopyContents{ std::nullopt };
+        core->CopyToClipboard([&](auto&&, auto& args) {
+            VERIFY_IS_TRUE(expectedCopyContents.has_value());
+            const std::wstring expected{ expectedCopyContents->c_str() };
+            const std::wstring actual{ args.Text().c_str() };
+            VERIFY_ARE_EQUAL(expected, actual);
+        });
+        bool expectedPaste = false;
+        interactivity->PasteFromClipboard([&](auto&&, auto&&) {
+            VERIFY_IS_TRUE(expectedPaste);
+        });
+
+        const auto originalViewport{ term.GetViewport() };
+        VERIFY_ARE_EQUAL(originalViewport.Width(), 30);
+
+        // For this test, don't use any modifiers
+        const auto modifiers = ControlKeyStates();
+        const auto leftMouseDown{ Control::MouseButtonState::IsLeftButtonDown };
+        const auto rightMouseDown{ Control::MouseButtonState::IsRightButtonDown };
+        const Control::MouseButtonState noMouseDown{};
+        const til::size fontSize{ 9, 21 };
+        const til::point terminalPosition0{ 0, 5 };
+        const til::point terminalPosition1{ 5, 5 };
+        const auto cursorPosition0{ terminalPosition0 * fontSize };
+        const auto cursorPosition1{ terminalPosition1 * fontSize };
+
+        Log::Comment(L" --- Click on the terminal at 0,5 ---");
+
+        interactivity->PointerPressed(leftMouseDown,
+                                      WM_LBUTTONDOWN, //pointerUpdateKind
+                                      0, // timestamp
+                                      modifiers,
+                                      cursorPosition0.to_core_point());
+        VERIFY_IS_FALSE(core->HasSelection());
+
+        Log::Comment(L" --- Drag to 5,5 ---");
+
+        interactivity->PointerMoved(leftMouseDown,
+                                    WM_LBUTTONDOWN, //pointerUpdateKind
+                                    modifiers,
+                                    true, // focused,
+                                    cursorPosition1.to_core_point(),
+                                    true); // pointerPressedInBounds
+        VERIFY_IS_TRUE(core->HasSelection());
+        // expectedCopyContents being nullopt here will ensure that we don't send the copy event till the pointer released
+
+        Log::Comment(L" --- Release the mouse --- ");
+        expectedCopyContents = L"line 5";
+        interactivity->PointerReleased(noMouseDown,
+                                       WM_LBUTTONUP, //pointerUpdateKind
+                                       modifiers,
+                                       cursorPosition1.to_core_point());
+        VERIFY_IS_TRUE(core->HasSelection());
+
+        Log::Comment(L" --- Right-click to paste --- ");
+        // Note from GH#14464: we don't want to copy _again_ at this point. The
+        // copy occured when the selection was made, we shouldn't stealth-update
+        // the clipboard again.
+        expectedCopyContents = std::nullopt;
+        expectedPaste = true;
+        interactivity->PointerPressed(rightMouseDown,
+                                      WM_RBUTTONDOWN, //pointerUpdateKind
+                                      0, // timestamp
+                                      modifiers,
+                                      cursorPosition1.to_core_point());
+        VERIFY_IS_FALSE(core->HasSelection());
+    }
+
+    void ControlInteractivityTests::CopyOnSelectAltBuffer()
+    {
+        // This test was inspired by GH#14464. Ultimately, it's similar to the
+        // CopyOnSelectSimple, just with an alt buffer, and outputting text
+        // after the selection was made.
+        auto [settings, conn] = _createSettingsAndConnection();
+        settings->CopyOnSelect(true);
+        auto [core, interactivity] = _createCoreAndInteractivity(*settings, *conn);
+        _standardInit(core, interactivity);
+        auto& term{ *core->_terminal };
+
+        Log::Comment(L" --- Switch to alt buffer ---");
+        term.Write(L"\x1b[?1049h");
+        auto returnToMain = wil::scope_exit([&]() { term.Write(L"\x1b[?1049h"); });
+
+        // Output some text
+        auto i = 0;
+        for (i = 0; i < core->ViewHeight() - 1; ++i)
+        {
+            conn->WriteInput(winrt::hstring{ fmt::format(L"line {}\r\n", i) });
+        }
+
+        // A callback for checking Copy events. expectedCopyContents=nullopt
+        // indicates that we're not expecting any copy events.
+        std::optional<std::wstring> expectedCopyContents{ std::nullopt };
+        core->CopyToClipboard([&](auto&&, auto& args) {
+            VERIFY_IS_TRUE(expectedCopyContents.has_value());
+            const std::wstring expected{ expectedCopyContents->c_str() };
+            const std::wstring actual{ args.Text().c_str() };
+            VERIFY_ARE_EQUAL(expected, actual);
+        });
+        bool expectedPaste = false;
+        interactivity->PasteFromClipboard([&](auto&&, auto&&) {
+            VERIFY_IS_TRUE(expectedPaste);
+        });
+
+        const auto originalViewport{ term.GetViewport() };
+        VERIFY_ARE_EQUAL(originalViewport.Width(), 30);
+
+        // For this test, don't use any modifiers
+        const auto modifiers = ControlKeyStates();
+        const auto leftMouseDown{ Control::MouseButtonState::IsLeftButtonDown };
+        const auto rightMouseDown{ Control::MouseButtonState::IsRightButtonDown };
+        const Control::MouseButtonState noMouseDown{};
+        const til::size fontSize{ 9, 21 };
+        const til::point terminalPosition0{ 0, 5 };
+        const til::point terminalPosition1{ 5, 5 };
+        const auto cursorPosition0{ terminalPosition0 * fontSize };
+        const auto cursorPosition1{ terminalPosition1 * fontSize };
+
+        Log::Comment(L" --- Click on the terminal at 0,5 ---");
+
+        interactivity->PointerPressed(leftMouseDown,
+                                      WM_LBUTTONDOWN, //pointerUpdateKind
+                                      0, // timestamp
+                                      modifiers,
+                                      cursorPosition0.to_core_point());
+        VERIFY_IS_FALSE(core->HasSelection());
+
+        Log::Comment(L" --- Drag to 5,5 ---");
+
+        interactivity->PointerMoved(leftMouseDown,
+                                    WM_LBUTTONDOWN, //pointerUpdateKind
+                                    modifiers,
+                                    true, // focused,
+                                    cursorPosition1.to_core_point(),
+                                    true); // pointerPressedInBounds
+        VERIFY_IS_TRUE(core->HasSelection());
+        // expectedCopyContents being nullopt here will ensure that we don't send the copy event till the pointer released
+
+        Log::Comment(L" --- Release the mouse --- ");
+        expectedCopyContents = L"line 5";
+        interactivity->PointerReleased(noMouseDown,
+                                       WM_LBUTTONUP, //pointerUpdateKind
+                                       modifiers,
+                                       cursorPosition1.to_core_point());
+        VERIFY_IS_TRUE(core->HasSelection());
+
+        // Output some text
+        for (; i < 5; ++i)
+        {
+            conn->WriteInput(winrt::hstring{ fmt::format(L"line {}\r\n", i) });
+        }
+
+        Log::Comment(L" --- Right-click to paste --- ");
+        expectedCopyContents = std::nullopt;
+        expectedPaste = true;
+        interactivity->PointerPressed(rightMouseDown,
+                                      WM_RBUTTONDOWN, //pointerUpdateKind
+                                      0, // timestamp
+                                      modifiers,
+                                      cursorPosition1.to_core_point());
+        VERIFY_IS_FALSE(core->HasSelection());
+    }
 }