diff --git a/src/cascadia/TerminalControl/ControlCore.cpp b/src/cascadia/TerminalControl/ControlCore.cpp
index cffc4e91a8..644bb2c0bc 100644
--- a/src/cascadia/TerminalControl/ControlCore.cpp
+++ b/src/cascadia/TerminalControl/ControlCore.cpp
@@ -1787,6 +1787,15 @@ namespace winrt::Microsoft::Terminal::Control::implementation
     void ControlCore::ClearSearch()
     {
         const auto lock = _terminal->LockForWriting();
+
+        // GH #19358: select the focused search result before clearing search
+        if (const auto focusedSearchResult = _terminal->GetSearchHighlightFocused())
+        {
+            _terminal->SetSelectionAnchor(focusedSearchResult->start);
+            _terminal->SetSelectionEnd(focusedSearchResult->end);
+            _renderer->TriggerSelection();
+        }
+
         _terminal->SetSearchHighlights({});
         _terminal->SetSearchHighlightFocused(0);
         _renderer->TriggerSearchHighlight(_searcher.Results());
diff --git a/src/cascadia/TerminalCore/TerminalSelection.cpp b/src/cascadia/TerminalCore/TerminalSelection.cpp
index f316cc782a..6942fb9ea5 100644
--- a/src/cascadia/TerminalCore/TerminalSelection.cpp
+++ b/src/cascadia/TerminalCore/TerminalSelection.cpp
@@ -362,10 +362,30 @@ void Terminal::ToggleMarkMode()
     {
         // Enter Mark Mode
         // NOTE: directly set cursor state. We already should have locked before calling this function.
-        if (!IsSelectionActive())
+        if (IsSelectionActive())
+        {
+            // Selection already existed --> just target "end"
+            if (WI_AreAllFlagsClear(_selectionEndpoint, SelectionEndpoint::Start | SelectionEndpoint::End))
+            {
+                WI_SetFlag(_selectionEndpoint, SelectionEndpoint::End);
+            }
+        }
+        else if (const auto focusedSearchResult = GetSearchHighlightFocused())
+        {
+            // We have a focused search result --> treat it as selection
+            *_selection.write() = SelectionInfo{
+                .start = focusedSearchResult->start,
+                .end = focusedSearchResult->end,
+                .pivot = focusedSearchResult->start,
+                .blockSelection = false,
+                .active = true,
+            };
+            WI_SetFlag(_selectionEndpoint, SelectionEndpoint::End);
+        }
+        else
         {
             // If we're scrolled up, use the viewport origin as the selection start.
-            // Otherwise, use the cursor position.
+            // Otherwise, just use the cursor position.
             const auto cursorPos = _scrollOffset != 0 ? _GetVisibleViewport().Origin() :
                                                         _activeBuffer().GetCursor().GetPosition();
             *_selection.write() = SelectionInfo{
@@ -377,11 +397,6 @@ void Terminal::ToggleMarkMode()
             };
             WI_SetAllFlags(_selectionEndpoint, SelectionEndpoint::Start | SelectionEndpoint::End);
         }
-        else if (WI_AreAllFlagsClear(_selectionEndpoint, SelectionEndpoint::Start | SelectionEndpoint::End))
-        {
-            // Selection already existed
-            WI_SetFlag(_selectionEndpoint, SelectionEndpoint::End);
-        }
         _ScrollToPoint(_selection->start);
         _selectionMode = SelectionInteractionMode::Mark;
         _selectionIsTargetingUrl = false;