diff --git a/stl/inc/filesystem b/stl/inc/filesystem
index 4b2ad4ce9b8..a08e435d4cc 100644
--- a/stl/inc/filesystem
+++ b/stl/inc/filesystem
@@ -1377,6 +1377,35 @@ namespace filesystem {
 #endif // ^^^ !_HAS_CXX20 ^^^
 
         _NODISCARD_FRIEND path operator/(const path& _Left, const path& _Right) { // append a pair of paths together
+            const auto _Right_size  = _Right._Text.size();
+            const auto _Right_first = _Right._Text.data();
+            const auto _Right_last  = _Right_first + _Right_size;
+
+            // Handle the most common case: !has_root_name(_Right) && !has_root_directory(_Right)
+            if (_Right_size != 0 && !_Has_drive_letter_prefix(_Right_first, _Right_last) && !_Is_slash(*_Right_first)) {
+                const auto _Left_size  = _Left._Text.size();
+                const auto _Left_first = _Left._Text.data();
+                const auto _Left_last  = _Left_first + _Left_size;
+
+                // Appending a slash to "X:" would make it an absolute path
+                const bool _Left_is_just_drive = _Left_size == 2 && _Is_drive_prefix(_Left_first);
+                const bool _Is_slash_needed    = _Left_size != 0 && !_Left_is_just_drive && !_Is_slash(_Left_last[-1]);
+
+                const auto _Total_size = _Left_size + static_cast<size_t>(_Is_slash_needed) + _Right_size;
+
+                path _Tmp;
+                _Tmp._Text._Resize_and_overwrite(_Total_size, [=](wchar_t* _Ptr, const size_t _Size) {
+                    _CSTD memcpy(_Ptr, _Left_first, _Left_size * sizeof(wchar_t));
+                    _Ptr += _Left_size;
+                    if (_Is_slash_needed) {
+                        *_Ptr++ = preferred_separator;
+                    }
+                    _CSTD memcpy(_Ptr, _Right_first, _Right_size * sizeof(wchar_t));
+                    return _Size;
+                });
+                return _Tmp;
+            }
+
             path _Tmp = _Left;
             _Tmp /= _Right;
             return _Tmp;
diff --git a/tests/std/tests/P0218R1_filesystem/test.cpp b/tests/std/tests/P0218R1_filesystem/test.cpp
index d3ea57bbbc8..e2d66ba01b2 100644
--- a/tests/std/tests/P0218R1_filesystem/test.cpp
+++ b/tests/std/tests/P0218R1_filesystem/test.cpp
@@ -544,6 +544,7 @@ struct slash_test_case {
 };
 
 constexpr slash_test_case slashTestCases[] = {
+    {L""sv, L""sv, L""sv},
     {L"relative"sv, L"other"sv, LR"(relative\other)"sv},
     {L"//server"sv, L"share"sv, LR"(//server\share)"sv},
     {L"//server/"sv, L"share"sv, LR"(//server/share)"sv},
@@ -555,6 +556,7 @@ constexpr slash_test_case slashTestCases[] = {
     {L""sv, L"cat"sv, L"cat"sv},
     {L"./"sv, L"cat"sv, L"./cat"sv}, // original test case catching a bug in the above
     {L"c:"sv, L""sv, L"c:"sv},
+    {L"c:"sv, L"dog"sv, L"c:dog"sv},
     {L"c:cat"sv, L"/dog"sv, L"c:/dog"sv},
     {L"c:/cat"sv, L"/dog"sv, L"c:/dog"sv},
     {L"c:cat"sv, L"c:dog"sv, LR"(c:cat\dog)"sv},
@@ -568,13 +570,23 @@ constexpr slash_test_case slashTestCases[] = {
 bool run_slash_test_case(const slash_test_case& testCase) {
     path p(testCase.a);
     p /= testCase.b;
-    if (p.native() == testCase.expected) {
-        return true;
+
+    if (p.native() != testCase.expected) {
+        wcerr << L"With operator/=, expected " << testCase.a << L" / " << testCase.b << L" to be " << testCase.expected
+              << L" but it was " << p.native() << L"\n";
+        return false;
     }
 
-    wcerr << L"Expected " << testCase.a << L" / " << testCase.b << L" to be " << testCase.expected << L" but it was "
-          << p.native() << L"\n";
-    return false;
+    // Also test operator/, which was optimized by GH-4136.
+    p = path{testCase.a} / path{testCase.b};
+
+    if (p.native() != testCase.expected) {
+        wcerr << L"With operator/, expected " << testCase.a << L" / " << testCase.b << L" to be " << testCase.expected
+              << L" but it was " << p.native() << L"\n";
+        return false;
+    }
+
+    return true;
 }
 
 void test_iterators() {