diff --git a/stl/inc/filesystem b/stl/inc/filesystem
index 8b93dd566d4..a2f4bd1dd09 100644
--- a/stl/inc/filesystem
+++ b/stl/inc/filesystem
@@ -102,6 +102,32 @@ namespace filesystem {
         return _Output;
     }
 
+    // More lenient version of _Convert_wide_to_narrow: Instead of failing on non-representable characters,
+    // replace them with a replacement character.
+    template <class _Traits, class _Alloc>
+    _NODISCARD basic_string<typename _Traits::char_type, _Traits, _Alloc> _Convert_wide_to_narrow_replace_chars(
+        const __std_code_page _Code_page, const wstring_view _Input, const _Alloc& _Al) {
+        basic_string<typename _Traits::char_type, _Traits, _Alloc> _Output(_Al);
+
+        if (!_Input.empty()) {
+            if (_Input.size() > static_cast<size_t>(INT_MAX)) {
+                _Throw_system_error(errc::invalid_argument);
+            }
+
+            const int _Len = _Check_convert_result(__std_fs_convert_wide_to_narrow_replace_chars(
+                _Code_page, _Input.data(), static_cast<int>(_Input.size()), nullptr, 0));
+
+            _Output.resize(static_cast<size_t>(_Len));
+
+            const auto _Data_as_char = reinterpret_cast<char*>(_Output.data());
+
+            (void) _Check_convert_result(__std_fs_convert_wide_to_narrow_replace_chars(
+                _Code_page, _Input.data(), static_cast<int>(_Input.size()), _Data_as_char, _Len));
+        }
+
+        return _Output;
+    }
+
     _NODISCARD inline wstring _Convert_utf32_to_wide(const u32string_view _Input) {
         wstring _Output;
 
@@ -1786,8 +1812,12 @@ namespace filesystem {
         static string _Pretty_message(const string_view _Op, const path& _Path1, const path& _Path2 = {}) {
             using namespace _STD string_view_literals; // TRANSITION, VSO-571749
             string _Result;
-            const string _Path1_str = _Path1.string();
-            const string _Path2_str = _Path2.string();
+            // Convert the paths to narrow encoding in a way that gracefully handles non-encodable characters
+            const auto _Code_page   = __std_fs_code_page();
+            const string _Path1_str = _Convert_wide_to_narrow_replace_chars<char_traits<char>>(
+                _Code_page, _Path1.native(), allocator<char>{});
+            const string _Path2_str = _Convert_wide_to_narrow_replace_chars<char_traits<char>>(
+                _Code_page, _Path2.native(), allocator<char>{});
             _Result.reserve(_Op.size() + (_Path2_str.empty() ? 4 : 8) + _Path1_str.size() + _Path2_str.size());
             _Result += _Op;
             _Result += R"(: ")"sv; // 3 chars
diff --git a/stl/inc/xfilesystem_abi.h b/stl/inc/xfilesystem_abi.h
index 0d3ce7035a9..2e3fcddde59 100644
--- a/stl/inc/xfilesystem_abi.h
+++ b/stl/inc/xfilesystem_abi.h
@@ -276,6 +276,10 @@ _NODISCARD __std_fs_convert_result __stdcall __std_fs_convert_wide_to_narrow(_In
     _In_reads_(_Input_len) const wchar_t* _Input_str, _In_ int _Input_len,
     _Out_writes_opt_(_Output_len) char* _Output_str, _In_ int _Output_len) noexcept;
 
+_NODISCARD __std_fs_convert_result __stdcall __std_fs_convert_wide_to_narrow_replace_chars(
+    _In_ __std_code_page _Code_page, _In_reads_(_Input_len) const wchar_t* _Input_str, _In_ int _Input_len,
+    _Out_writes_opt_(_Output_len) char* _Output_str, _In_ int _Output_len) noexcept;
+
 _NODISCARD __std_win_error __stdcall __std_fs_get_file_id(
     _Out_ __std_fs_file_id* _Id, _In_z_ const wchar_t* _Path) noexcept;
 
diff --git a/stl/src/filesystem.cpp b/stl/src/filesystem.cpp
index ca312314f04..0a1d3d5a1e8 100644
--- a/stl/src/filesystem.cpp
+++ b/stl/src/filesystem.cpp
@@ -421,6 +421,27 @@ void __stdcall __std_fs_directory_iterator_close(const __std_fs_dir_handle _Hand
     return _Result;
 }
 
+[[nodiscard]] __std_fs_convert_result __stdcall __std_fs_convert_wide_to_narrow_replace_chars(
+    const __std_code_page _Code_page, const wchar_t* const _Input_str, const int _Input_len, char* const _Output_str,
+    const int _Output_len) noexcept {
+    __std_fs_convert_result _Result;
+
+    _Result._Len = WideCharToMultiByte(static_cast<unsigned int>(_Code_page), WC_NO_BEST_FIT_CHARS, _Input_str,
+        _Input_len, _Output_str, _Output_len, nullptr, nullptr);
+
+    _Result._Err = _Result._Len == 0 ? __std_win_error{GetLastError()} : __std_win_error::_Success;
+
+    // Some codepages don't support WC_NO_BEST_FIT_CHARS, fall back to default conversion.
+    if (_Result._Err == __std_win_error{ERROR_INVALID_FLAGS}) {
+        _Result._Len = WideCharToMultiByte(static_cast<unsigned int>(_Code_page), 0, _Input_str, _Input_len,
+            _Output_str, _Output_len, nullptr, nullptr);
+
+        _Result._Err = _Result._Len == 0 ? __std_win_error{GetLastError()} : __std_win_error::_Success;
+    }
+
+    return _Result;
+}
+
 [[nodiscard]] __std_fs_copy_file_result __stdcall __std_fs_copy_file(const wchar_t* const _Source,
     const wchar_t* const _Target, __std_fs_copy_options _Options) noexcept { // copy _Source to _Target
     _Options &= __std_fs_copy_options::_Existing_mask;
diff --git a/tests/std/test.lst b/tests/std/test.lst
index 6358d0afa94..4f9f2c4bc34 100644
--- a/tests/std/test.lst
+++ b/tests/std/test.lst
@@ -160,6 +160,7 @@ tests\GH_000545_include_compare
 tests\GH_000685_condition_variable_any
 tests\GH_000690_overaligned_function
 tests\GH_000890_pow_template
+tests\GH_001010_filesystem_error_encoding
 tests\LWG2597_complex_branch_cut
 tests\LWG3018_shared_ptr_function
 tests\P0024R2_parallel_algorithms_adjacent_difference
diff --git a/tests/std/tests/GH_001010_filesystem_error_encoding/env.lst b/tests/std/tests/GH_001010_filesystem_error_encoding/env.lst
new file mode 100644
index 00000000000..2de7aab2959
--- /dev/null
+++ b/tests/std/tests/GH_001010_filesystem_error_encoding/env.lst
@@ -0,0 +1,4 @@
+# Copyright (c) Microsoft Corporation.
+# SPDX-License-Identifier: Apache-2.0 WITH LLVM-exception
+
+RUNALL_INCLUDE ..\usual_17_matrix.lst
diff --git a/tests/std/tests/GH_001010_filesystem_error_encoding/test.cpp b/tests/std/tests/GH_001010_filesystem_error_encoding/test.cpp
new file mode 100644
index 00000000000..a823c2599a2
--- /dev/null
+++ b/tests/std/tests/GH_001010_filesystem_error_encoding/test.cpp
@@ -0,0 +1,33 @@
+// Copyright (c) Microsoft Corporation.
+// SPDX-License-Identifier: Apache-2.0 WITH LLVM-exception
+
+#include <assert.h>
+#include <exception>
+#include <filesystem>
+#include <string_view>
+#include <system_error>
+
+using namespace std;
+namespace fs = std::filesystem;
+
+void test_filesystem_error_with_bad_codepage_characters() {
+    fs::path problem_path{L"problematic\xD83Dtestpath"}; // path containing lone high surrogate
+
+    // Make sure the path is not encodable in our current locale, otherwise the test tests nothing
+    bool exception_caught = false;
+    try {
+        (void) problem_path.string();
+    } catch (const exception&) {
+        exception_caught = true;
+    }
+    assert(exception_caught);
+
+    // filesystem_error should handle the non-encodable character gracefully when building its message
+    fs::filesystem_error err{"testexception", problem_path, error_code{}};
+    assert(string_view{err.what()}.find("problematic") != string_view::npos);
+    assert(string_view{err.what()}.find("testpath") != string_view::npos);
+}
+
+int main() {
+    test_filesystem_error_with_bad_codepage_characters();
+}