diff --git a/src/buffer/out/search.cpp b/src/buffer/out/search.cpp
index bfa66569dff..31c7081b2b9 100644
--- a/src/buffer/out/search.cpp
+++ b/src/buffer/out/search.cpp
@@ -25,7 +25,9 @@ bool Search::Reset(Microsoft::Console::Render::IRenderData& renderData, const st
     _flags = flags;
     _lastMutationId = textBuffer.GetLastMutationId();
 
-    _ok = textBuffer.SearchText(needle, _flags, _results);
+    auto result = textBuffer.SearchText(needle, _flags);
+    _ok = result.has_value();
+    _results = std::move(result).value_or(std::vector<til::point_span>{});
     _index = reverse ? gsl::narrow_cast<ptrdiff_t>(_results.size()) - 1 : 0;
     _step = reverse ? -1 : 1;
     return true;
@@ -144,3 +146,8 @@ ptrdiff_t Search::CurrentMatch() const noexcept
 {
     return _index;
 }
+
+bool Search::IsOk() const noexcept
+{
+    return _ok;
+}
diff --git a/src/buffer/out/search.h b/src/buffer/out/search.h
index 3ceb71564da..763b5d40c73 100644
--- a/src/buffer/out/search.h
+++ b/src/buffer/out/search.h
@@ -49,6 +49,7 @@ class Search final
     const std::vector<til::point_span>& Results() const noexcept;
     std::vector<til::point_span>&& ExtractResults() noexcept;
     ptrdiff_t CurrentMatch() const noexcept;
+    bool IsOk() const noexcept;
 
 private:
     // _renderData is a pointer so that Search() is constexpr default constructable.
@@ -57,6 +58,7 @@ class Search final
     SearchFlag _flags{};
     uint64_t _lastMutationId = 0;
 
+    bool _ok{ false };
     std::vector<til::point_span> _results;
     ptrdiff_t _index = 0;
     ptrdiff_t _step = 0;
diff --git a/src/buffer/out/textBuffer.cpp b/src/buffer/out/textBuffer.cpp
index ec5157b2b6e..af60c0443dc 100644
--- a/src/buffer/out/textBuffer.cpp
+++ b/src/buffer/out/textBuffer.cpp
@@ -3185,14 +3185,15 @@ void TextBuffer::CopyHyperlinkMaps(const TextBuffer& other)
 
 // Searches through the entire (committed) text buffer for `needle` and returns the coordinates in absolute coordinates.
 // The end coordinates of the returned ranges are considered inclusive.
-std::vector<til::point_span> TextBuffer::SearchText(const std::wstring_view& needle, SearchFlag flags) const
+std::optional<std::vector<til::point_span>> TextBuffer::SearchText(const std::wstring_view& needle, SearchFlag flags) const
 {
     return SearchText(needle, flags, 0, til::CoordTypeMax);
 }
 
 // Searches through the given rows [rowBeg,rowEnd) for `needle` and returns the coordinates in absolute coordinates.
 // While the end coordinates of the returned ranges are considered inclusive, the [rowBeg,rowEnd) range is half-open.
-std::vector<til::point_span> TextBuffer::SearchText(const std::wstring_view& needle, SearchFlag flags, til::CoordType rowBeg, til::CoordType rowEnd) const
+// Returns nullopt if the parameters were invalid (e.g. regex search was requested with an invalid regex)
+std::optional<std::vector<til::point_span>> TextBuffer::SearchText(const std::wstring_view& needle, SearchFlag flags, til::CoordType rowBeg, til::CoordType rowEnd) const
 {
     rowEnd = std::min(rowEnd, _estimateOffsetOfLastCommittedRow() + 1);
 
@@ -3220,6 +3221,11 @@ std::vector<til::point_span> TextBuffer::SearchText(const std::wstring_view& nee
 
     UErrorCode status = U_ZERO_ERROR;
     const auto re = ICU::CreateRegex(needle, icuFlags, &status);
+    if (status > U_ZERO_ERROR)
+    {
+        return std::nullopt;
+    }
+
     uregex_setUText(re.get(), &text, &status);
 
     if (uregex_find(re.get(), -1, &status))
diff --git a/src/buffer/out/textBuffer.hpp b/src/buffer/out/textBuffer.hpp
index 3bbb7cbdfca..6f21ad41cb4 100644
--- a/src/buffer/out/textBuffer.hpp
+++ b/src/buffer/out/textBuffer.hpp
@@ -294,8 +294,8 @@ class TextBuffer final
 
     static void Reflow(TextBuffer& oldBuffer, TextBuffer& newBuffer, const Microsoft::Console::Types::Viewport* lastCharacterViewport = nullptr, PositionInformation* positionInfo = nullptr);
 
-    std::vector<til::point_span> SearchText(const std::wstring_view& needle, SearchFlag flags) const;
-    std::vector<til::point_span> SearchText(const std::wstring_view& needle, SearchFlag flags, til::CoordType rowBeg, til::CoordType rowEnd) const;
+    std::optional<std::vector<til::point_span>> SearchText(const std::wstring_view& needle, SearchFlag flags) const;
+    std::optional<std::vector<til::point_span>> SearchText(const std::wstring_view& needle, SearchFlag flags, til::CoordType rowBeg, til::CoordType rowEnd) const;
 
     // Mark handling
     std::vector<ScrollMark> GetMarkRows() const;
diff --git a/src/cascadia/TerminalControl/ControlCore.cpp b/src/cascadia/TerminalControl/ControlCore.cpp
index 340301c64c2..5e6b79e2862 100644
--- a/src/cascadia/TerminalControl/ControlCore.cpp
+++ b/src/cascadia/TerminalControl/ControlCore.cpp
@@ -1654,11 +1654,12 @@ namespace winrt::Microsoft::Terminal::Control::implementation
     // - resetOnly: If true, only Reset() will be called, if anything. FindNext() will never be called.
     // Return Value:
     // - <none>
-    SearchResults ControlCore::Search(const std::wstring_view& text, const bool goForward, const bool caseSensitive, const bool resetOnly)
+    SearchResults ControlCore::Search(const std::wstring_view& text, const bool goForward, const bool caseSensitive, const bool regularExpression, const bool resetOnly)
     {
         const auto lock = _terminal->LockForWriting();
         SearchFlag flags{};
         WI_SetFlagIf(flags, SearchFlag::CaseInsensitive, !caseSensitive);
+        WI_SetFlagIf(flags, SearchFlag::RegularExpression, regularExpression);
         const auto searchInvalidated = _searcher.IsStale(*_terminal.get(), text, flags);
 
         if (searchInvalidated || !resetOnly)
@@ -1702,6 +1703,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
             .TotalMatches = totalMatches,
             .CurrentMatch = currentMatch,
             .SearchInvalidated = searchInvalidated,
+            .SearchRegexInvalid = !_searcher.IsOk(),
         };
     }
 
diff --git a/src/cascadia/TerminalControl/ControlCore.h b/src/cascadia/TerminalControl/ControlCore.h
index 1eb4b532c49..0798cc6c1fe 100644
--- a/src/cascadia/TerminalControl/ControlCore.h
+++ b/src/cascadia/TerminalControl/ControlCore.h
@@ -219,7 +219,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         void SetSelectionAnchor(const til::point position);
         void SetEndSelectionPoint(const til::point position);
 
-        SearchResults Search(const std::wstring_view& text, bool goForward, bool caseSensitive, bool reset);
+        SearchResults Search(const std::wstring_view& text, bool goForward, bool caseSensitive, bool regularExpression, bool reset);
         const std::vector<til::point_span>& SearchResultRows() const noexcept;
         void ClearSearch();
         void SnapSearchResultToSelection(bool snap) noexcept;
diff --git a/src/cascadia/TerminalControl/ControlCore.idl b/src/cascadia/TerminalControl/ControlCore.idl
index d10a963786e..4ded4e2ed89 100644
--- a/src/cascadia/TerminalControl/ControlCore.idl
+++ b/src/cascadia/TerminalControl/ControlCore.idl
@@ -54,6 +54,7 @@ namespace Microsoft.Terminal.Control
         Int32 TotalMatches;
         Int32 CurrentMatch;
         Boolean SearchInvalidated;
+        Boolean SearchRegexInvalid;
     };
 
     [default_interface] runtimeclass SelectionColor
@@ -134,7 +135,7 @@ namespace Microsoft.Terminal.Control
         void ResumeRendering();
         void BlinkAttributeTick();
 
-        SearchResults Search(String text, Boolean goForward, Boolean caseSensitive, Boolean reset);
+        SearchResults Search(String text, Boolean goForward, Boolean caseSensitive, Boolean regularExpression, Boolean reset);
         void ClearSearch();
         Boolean SnapSearchResultToSelection;
 
diff --git a/src/cascadia/TerminalControl/Resources/en-US/Resources.resw b/src/cascadia/TerminalControl/Resources/en-US/Resources.resw
index 328aa4a03cd..53bff1ce7f2 100644
--- a/src/cascadia/TerminalControl/Resources/en-US/Resources.resw
+++ b/src/cascadia/TerminalControl/Resources/en-US/Resources.resw
@@ -300,4 +300,16 @@ Please either install the missing font or choose another one.</value>
     <value>Restored</value>
     <comment>"Restored" as in "This content was restored"</comment>
   </data>
-</root>
\ No newline at end of file
+  <data name="SearchBox_RegularExpression.ToolTipService.ToolTip" xml:space="preserve">
+    <value>Regular Expression</value>
+    <comment>The tooltip text for the button on the search box control governing the use of "regular expressions" ("regex").</comment>
+  </data>
+  <data name="SearchBox_RegularExpression.[using:Windows.UI.Xaml.Automation]AutomationProperties.Name" xml:space="preserve">
+    <value>Regular Expression Search</value>
+    <comment>The accessibility description text for the button on the search box control governing the use of "regular expressions" ("regex").</comment>
+  </data>
+  <data name="SearchRegexInvalid" xml:space="preserve">
+    <value>invalid</value>
+    <comment>This brief message is displayed when a regular expression is invalid.</comment>
+  </data>
+</root>
diff --git a/src/cascadia/TerminalControl/SearchBoxControl.cpp b/src/cascadia/TerminalControl/SearchBoxControl.cpp
index eaaae04add9..46e27de04d4 100644
--- a/src/cascadia/TerminalControl/SearchBoxControl.cpp
+++ b/src/cascadia/TerminalControl/SearchBoxControl.cpp
@@ -30,6 +30,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         _focusableElements.insert(TextBox());
         _focusableElements.insert(CloseButton());
         _focusableElements.insert(CaseSensitivityButton());
+        _focusableElements.insert(RegexButton());
         _focusableElements.insert(GoForwardButton());
         _focusableElements.insert(GoBackwardButton());
 
@@ -224,6 +225,11 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         return CaseSensitivityButton().IsChecked().GetBoolean();
     }
 
+    bool SearchBoxControl::RegularExpression()
+    {
+        return RegexButton().IsChecked().GetBoolean();
+    }
+
     // Method Description:
     // - Handler for pressing Enter on TextBox, trigger
     //   text search
@@ -245,11 +251,11 @@ namespace winrt::Microsoft::Terminal::Control::implementation
             const auto state = CoreWindow::GetForCurrentThread().GetKeyState(winrt::Windows::System::VirtualKey::Shift);
             if (WI_IsFlagSet(state, CoreVirtualKeyStates::Down))
             {
-                Search.raise(Text(), !GoForward(), CaseSensitive());
+                Search.raise(Text(), !GoForward(), CaseSensitive(), RegularExpression());
             }
             else
             {
-                Search.raise(Text(), GoForward(), CaseSensitive());
+                Search.raise(Text(), GoForward(), CaseSensitive(), RegularExpression());
             }
             e.Handled(true);
         }
@@ -340,7 +346,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         }
 
         // kick off search
-        Search.raise(Text(), GoForward(), CaseSensitive());
+        Search.raise(Text(), GoForward(), CaseSensitive(), RegularExpression());
     }
 
     // Method Description:
@@ -361,7 +367,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         }
 
         // kick off search
-        Search.raise(Text(), GoForward(), CaseSensitive());
+        Search.raise(Text(), GoForward(), CaseSensitive(), RegularExpression());
     }
 
     // Method Description:
@@ -399,7 +405,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
     // - <none>
     void SearchBoxControl::TextBoxTextChanged(winrt::Windows::Foundation::IInspectable const& /*sender*/, winrt::Windows::UI::Xaml::RoutedEventArgs const& /*e*/)
     {
-        SearchChanged.raise(Text(), GoForward(), CaseSensitive());
+        SearchChanged.raise(Text(), GoForward(), CaseSensitive(), RegularExpression());
     }
 
     // Method Description:
@@ -411,7 +417,12 @@ namespace winrt::Microsoft::Terminal::Control::implementation
     // - <none>
     void SearchBoxControl::CaseSensitivityButtonClicked(winrt::Windows::Foundation::IInspectable const& /*sender*/, winrt::Windows::UI::Xaml::RoutedEventArgs const& /*e*/)
     {
-        SearchChanged.raise(Text(), GoForward(), CaseSensitive());
+        SearchChanged.raise(Text(), GoForward(), CaseSensitive(), RegularExpression());
+    }
+
+    void SearchBoxControl::RegexButtonClicked(winrt::Windows::Foundation::IInspectable const& /*sender*/, winrt::Windows::UI::Xaml::RoutedEventArgs const& /*e*/)
+    {
+        SearchChanged.raise(Text(), GoForward(), CaseSensitive(), RegularExpression());
     }
 
     // Method Description:
@@ -504,7 +515,8 @@ namespace winrt::Microsoft::Terminal::Control::implementation
     double SearchBoxControl::_GetStatusMaxWidth()
     {
         const auto fontSize = StatusBox().FontSize();
-        const auto maxLength = std::max({ _TextWidth(_FormatStatus(-1, -1), fontSize),
+        const auto maxLength = std::max({ _TextWidth(RS_(L"SearchRegexInvalid"), fontSize),
+                                          _TextWidth(_FormatStatus(-1, -1), fontSize),
                                           _TextWidth(_FormatStatus(0, -1), fontSize),
                                           _TextWidth(_FormatStatus(MaximumTotalResultsToShowInStatus, MaximumTotalResultsToShowInStatus - 1), fontSize),
                                           _TextWidth(_FormatStatus(MaximumTotalResultsToShowInStatus + 1, MaximumTotalResultsToShowInStatus - 1), fontSize),
@@ -521,9 +533,17 @@ namespace winrt::Microsoft::Terminal::Control::implementation
     // - currentMatch - the index of the current match (0-based)
     // Return Value:
     // - <none>
-    void SearchBoxControl::SetStatus(int32_t totalMatches, int32_t currentMatch)
+    void SearchBoxControl::SetStatus(int32_t totalMatches, int32_t currentMatch, bool searchRegexInvalid)
     {
-        const auto status = _FormatStatus(totalMatches, currentMatch);
+        hstring status;
+        if (searchRegexInvalid)
+        {
+            status = RS_(L"SearchRegexInvalid");
+        }
+        else
+        {
+            status = _FormatStatus(totalMatches, currentMatch);
+        }
         StatusBox().Text(status);
     }
 
diff --git a/src/cascadia/TerminalControl/SearchBoxControl.h b/src/cascadia/TerminalControl/SearchBoxControl.h
index 60ea00da481..d774e42b569 100644
--- a/src/cascadia/TerminalControl/SearchBoxControl.h
+++ b/src/cascadia/TerminalControl/SearchBoxControl.h
@@ -38,10 +38,11 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         winrt::hstring Text();
         bool GoForward();
         bool CaseSensitive();
+        bool RegularExpression();
         void SetFocusOnTextbox();
         void PopulateTextbox(const winrt::hstring& text);
         bool ContainsFocus();
-        void SetStatus(int32_t totalMatches, int32_t currentMatch);
+        void SetStatus(int32_t totalMatches, int32_t currentMatch, bool searchRegexInvalid);
         void ClearStatus();
 
         void GoBackwardClicked(const winrt::Windows::Foundation::IInspectable& /*sender*/, const winrt::Windows::UI::Xaml::RoutedEventArgs& /*e*/);
@@ -50,6 +51,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
 
         void TextBoxTextChanged(winrt::Windows::Foundation::IInspectable const& sender, winrt::Windows::UI::Xaml::RoutedEventArgs const& e);
         void CaseSensitivityButtonClicked(winrt::Windows::Foundation::IInspectable const& sender, winrt::Windows::UI::Xaml::RoutedEventArgs const& e);
+        void RegexButtonClicked(winrt::Windows::Foundation::IInspectable const& sender, winrt::Windows::UI::Xaml::RoutedEventArgs const& e);
         void SearchBoxPointerPressedHandler(winrt::Windows::Foundation::IInspectable const& /*sender*/, winrt::Windows::UI::Xaml::Input::PointerRoutedEventArgs const& e);
         void SearchBoxPointerReleasedHandler(winrt::Windows::Foundation::IInspectable const& /*sender*/, winrt::Windows::UI::Xaml::Input::PointerRoutedEventArgs const& e);
 
diff --git a/src/cascadia/TerminalControl/SearchBoxControl.idl b/src/cascadia/TerminalControl/SearchBoxControl.idl
index 3abf4f50229..61c133b1cce 100644
--- a/src/cascadia/TerminalControl/SearchBoxControl.idl
+++ b/src/cascadia/TerminalControl/SearchBoxControl.idl
@@ -3,7 +3,7 @@
 
 namespace Microsoft.Terminal.Control
 {
-    delegate void SearchHandler(String query, Boolean goForward, Boolean isCaseSensitive);
+    delegate void SearchHandler(String query, Boolean goForward, Boolean isCaseSensitive, Boolean regularExpression);
 
     [default_interface] runtimeclass SearchBoxControl : Windows.UI.Xaml.Controls.UserControl, Windows.UI.Xaml.Data.INotifyPropertyChanged
     {
@@ -11,7 +11,6 @@ namespace Microsoft.Terminal.Control
         void SetFocusOnTextbox();
         void PopulateTextbox(String text);
         Boolean ContainsFocus();
-        void SetStatus(Int32 totalMatches, Int32 currentMatch);
         void ClearStatus();
         Windows.Foundation.Rect ContentClipRect{ get; };
         Double OpenAnimationStartPoint{ get; };
diff --git a/src/cascadia/TerminalControl/SearchBoxControl.xaml b/src/cascadia/TerminalControl/SearchBoxControl.xaml
index c17fcc3c010..7523cdcfc83 100644
--- a/src/cascadia/TerminalControl/SearchBoxControl.xaml
+++ b/src/cascadia/TerminalControl/SearchBoxControl.xaml
@@ -243,6 +243,17 @@
             <PathIcon Data="M8.87305 10H7.60156L6.5625 7.25195H2.40625L1.42871 10H0.150391L3.91016 0.197266H5.09961L8.87305 10ZM6.18652 6.21973L4.64844 2.04297C4.59831 1.90625 4.54818 1.6875 4.49805 1.38672H4.4707C4.42513 1.66471 4.37272 1.88346 4.31348 2.04297L2.78906 6.21973H6.18652ZM15.1826 10H14.0615V8.90625H14.0342C13.5465 9.74479 12.8288 10.1641 11.8809 10.1641C11.1836 10.1641 10.6367 9.97949 10.2402 9.61035C9.84831 9.24121 9.65234 8.7513 9.65234 8.14062C9.65234 6.83268 10.4225 6.07161 11.9629 5.85742L14.0615 5.56348C14.0615 4.37402 13.5807 3.7793 12.6191 3.7793C11.776 3.7793 11.015 4.06641 10.3359 4.64062V3.49219C11.0241 3.05469 11.8171 2.83594 12.7148 2.83594C14.36 2.83594 15.1826 3.70638 15.1826 5.44727V10ZM14.0615 6.45898L12.373 6.69141C11.8535 6.76432 11.4616 6.89421 11.1973 7.08105C10.9329 7.26335 10.8008 7.58919 10.8008 8.05859C10.8008 8.40039 10.9215 8.68066 11.1631 8.89941C11.4092 9.11361 11.735 9.2207 12.1406 9.2207C12.6966 9.2207 13.1546 9.02702 13.5146 8.63965C13.8792 8.24772 14.0615 7.75326 14.0615 7.15625V6.45898Z" />
         </ToggleButton>
 
+        <ToggleButton x:Name="RegexButton"
+                      x:Uid="SearchBox_RegularExpression"
+                      Width="32"
+                      Height="32"
+                      Margin="4,0"
+                      Padding="0"
+                      BackgroundSizing="OuterBorderEdge"
+                      Click="RegexButtonClicked">
+            <PathIcon Data="M 11.7716,12.7647 V 14.2481 H 11.06066 V 12.8194 C 10.08996,12.8194 9.30156,12.62344 8.69546,12.23151 V 11.04201 C 8.95978,11.27443 9.31981,11.4704 9.77556,11.6299 10.23585,11.78485 10.66423,11.86232 11.06076,11.86232 V 8.36232 C 10.05816,7.87925 9.40876,7.43491 9.11256,7.02932 8.81634,6.61916 8.66822,6.13609 8.66822,5.58012 8.66822,4.91931 8.89381,4.34962 9.34498,3.87112 9.79615,3.38805 10.36808,3.09866 11.06078,3.00296 V 1.77246 H 11.77172 V 2.97556 C 12.66495,3.002904 13.28242,3.13051 13.62422,3.35837 V 4.52047 C 13.15938,4.15589 12.54182,3.95992 11.77172,3.93258 V 7.54198 C 12.71964,7.99315 13.36682,8.43065 13.71312,8.85448 14.06403,9.27375 14.23949,9.75227 14.23949,10.28998 14.23949,10.93712 14.02074,11.48168 13.58324,11.92378 13.1503,12.36128 12.54644,12.64155 11.77174,12.7646 Z M 11.06066,7.1592 V 3.9737 C 10.67785,4.051174 10.37479,4.22207 10.15148,4.4864 9.92817,4.74617 9.81652,5.0629 9.81652,5.4366 9.81652,5.82853 9.90767,6.14982 10.08996,6.40047 10.27225,6.65112 10.59582,6.90405 11.06066,7.15926 Z M 11.7716,8.7178 V 11.8076 C 12.65116,11.61619 13.0909,11.14224 13.0909,10.3857 13.0909,9.75679 12.65112,9.2008 11.7716,8.7177 Z M 8.0089,8.5538 H 6.9835 L 4.714,4.3224 H 4.672984 L 2.560684,8.5538 H 1.555784 L 4.440584,2.8526 H 4.884924 Z " />
+        </ToggleButton>
+
         <Button x:Name="CloseButton"
                 x:Uid="SearchBox_Close"
                 Width="32"
diff --git a/src/cascadia/TerminalControl/TermControl.cpp b/src/cascadia/TerminalControl/TermControl.cpp
index 97fbdd46dc8..1e73832b02d 100644
--- a/src/cascadia/TerminalControl/TermControl.cpp
+++ b/src/cascadia/TerminalControl/TermControl.cpp
@@ -566,7 +566,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
         }
         else
         {
-            _handleSearchResults(_core.Search(_searchBox->Text(), goForward, _searchBox->CaseSensitive(), false));
+            _handleSearchResults(_core.Search(_searchBox->Text(), goForward, _searchBox->CaseSensitive(), _searchBox->RegularExpression(), false));
         }
     }
 
@@ -595,9 +595,10 @@ namespace winrt::Microsoft::Terminal::Control::implementation
     // - <none>
     void TermControl::_Search(const winrt::hstring& text,
                               const bool goForward,
-                              const bool caseSensitive)
+                              const bool caseSensitive,
+                              const bool regularExpression)
     {
-        _handleSearchResults(_core.Search(text, goForward, caseSensitive, false));
+        _handleSearchResults(_core.Search(text, goForward, caseSensitive, regularExpression, false));
     }
 
     // Method Description:
@@ -610,11 +611,12 @@ namespace winrt::Microsoft::Terminal::Control::implementation
     // - <none>
     void TermControl::_SearchChanged(const winrt::hstring& text,
                                      const bool goForward,
-                                     const bool caseSensitive)
+                                     const bool caseSensitive,
+                                     const bool regularExpression)
     {
         if (_searchBox && _searchBox->Visibility() == Visibility::Visible)
         {
-            _handleSearchResults(_core.Search(text, goForward, caseSensitive, false));
+            _handleSearchResults(_core.Search(text, goForward, caseSensitive, regularExpression, false));
         }
     }
 
@@ -3606,7 +3608,8 @@ namespace winrt::Microsoft::Terminal::Control::implementation
 
         const auto goForward = _searchBox->GoForward();
         const auto caseSensitive = _searchBox->CaseSensitive();
-        _handleSearchResults(_core.Search(text, goForward, caseSensitive, true));
+        const auto regularExpression = _searchBox->RegularExpression();
+        _handleSearchResults(_core.Search(text, goForward, caseSensitive, regularExpression, true));
     }
 
     void TermControl::_handleSearchResults(SearchResults results)
@@ -3616,7 +3619,7 @@ namespace winrt::Microsoft::Terminal::Control::implementation
             return;
         }
 
-        _searchBox->SetStatus(results.TotalMatches, results.CurrentMatch);
+        _searchBox->SetStatus(results.TotalMatches, results.CurrentMatch, results.SearchRegexInvalid);
 
         if (results.SearchInvalidated)
         {
diff --git a/src/cascadia/TerminalControl/TermControl.h b/src/cascadia/TerminalControl/TermControl.h
index 66995a92c63..75d49c3b317 100644
--- a/src/cascadia/TerminalControl/TermControl.h
+++ b/src/cascadia/TerminalControl/TermControl.h
@@ -371,8 +371,8 @@ namespace winrt::Microsoft::Terminal::Control::implementation
 
         double _GetAutoScrollSpeed(double cursorDistanceFromBorder) const;
 
-        void _Search(const winrt::hstring& text, const bool goForward, const bool caseSensitive);
-        void _SearchChanged(const winrt::hstring& text, const bool goForward, const bool caseSensitive);
+        void _Search(const winrt::hstring& text, const bool goForward, const bool caseSensitive, const bool regularExpression);
+        void _SearchChanged(const winrt::hstring& text, const bool goForward, const bool caseSensitive, const bool regularExpression);
         void _CloseSearchBoxControl(const winrt::Windows::Foundation::IInspectable& sender, const Windows::UI::Xaml::RoutedEventArgs& args);
         void _refreshSearch();
         void _handleSearchResults(SearchResults results);
diff --git a/src/cascadia/TerminalCore/Terminal.cpp b/src/cascadia/TerminalCore/Terminal.cpp
index 1579c07108b..929063d3c0c 100644
--- a/src/cascadia/TerminalCore/Terminal.cpp
+++ b/src/cascadia/TerminalCore/Terminal.cpp
@@ -1559,7 +1559,7 @@ void Terminal::ColorSelection(const TextAttribute& attr, winrt::Microsoft::Termi
 
                 if (!textView.empty())
                 {
-                    const auto hits = textBuffer.SearchText(textView, SearchFlag::CaseInsensitive);
+                    const auto hits = textBuffer.SearchText(textView, SearchFlag::CaseInsensitive).value_or(std::vector<til::point_span>{});
                     for (const auto& s : hits)
                     {
                         colorSelection(s.start, s.end, attr);
diff --git a/src/host/selectionInput.cpp b/src/host/selectionInput.cpp
index 4451d2ec27d..1fce41836f9 100644
--- a/src/host/selectionInput.cpp
+++ b/src/host/selectionInput.cpp
@@ -701,7 +701,7 @@ bool Selection::_HandleColorSelection(const INPUT_KEY_INFO* const pInputKeyInfo)
                     ClearSelection();
 
                     const auto& textBuffer = gci.renderData.GetTextBuffer();
-                    const auto hits = textBuffer.SearchText(str, SearchFlag::CaseInsensitive);
+                    const auto hits = textBuffer.SearchText(str, SearchFlag::CaseInsensitive).value_or(std::vector<til::point_span>{});
                     for (const auto& s : hits)
                     {
                         ColorSelection(s.start, s.end, selectionAttr);