diff --git a/Tests/LibRegex/Regex.cpp b/Tests/LibRegex/Regex.cpp
index c7d3f5f763917d..07b2b9fae0fd02 100644
--- a/Tests/LibRegex/Regex.cpp
+++ b/Tests/LibRegex/Regex.cpp
@@ -1033,6 +1033,8 @@ TEST_CASE(optimizer_atomic_groups)
         // (b+)(b+) produces an intermediate block with no matching ops, the optimiser should ignore that block when looking for following matches and correctly detect the overlap between (b+) and (b+).
         // note that the second loop may be rewritten to a ForkReplace, but the first loop should not be rewritten.
         Tuple { "(b+)(b+)"sv, "bbb"sv, true },
+        // Don't treat [\S] as [\s]; see ladybird#2296.
+        Tuple { "([^\\s]+?)\\(([\\s\\S]*)\\)"sv, "a(b)"sv, true },
     };
 
     for (auto& test : tests) {
diff --git a/Userland/Libraries/LibRegex/RegexOptimizer.cpp b/Userland/Libraries/LibRegex/RegexOptimizer.cpp
index c6fd94a2a7665b..a0d7e82703b2fb 100644
--- a/Userland/Libraries/LibRegex/RegexOptimizer.cpp
+++ b/Userland/Libraries/LibRegex/RegexOptimizer.cpp
@@ -221,7 +221,7 @@ static bool has_overlap(Vector<CompareTypeAndValuePair> const& lhs, Vector<Compa
             break;
         case CharacterCompareType::TemporaryInverse:
             temporary_inverse = true;
-            reset_temporary_inverse = true;
+            reset_temporary_inverse = false;
             break;
         case CharacterCompareType::AnyChar:
             // Special case: if not inverted, AnyChar is always in the range.
@@ -327,7 +327,7 @@ static bool has_overlap(Vector<CompareTypeAndValuePair> const& lhs, Vector<Compa
             break;
         case CharacterCompareType::TemporaryInverse:
             temporary_inverse = true;
-            reset_temporary_inverse = true;
+            reset_temporary_inverse = false;
             break;
         case CharacterCompareType::AnyChar:
             // Special case: if not inverted, AnyChar is always in the range.