diff --git a/pkg/vm_service/test/evaluate_optimized_out_variable_test.dart b/pkg/vm_service/test/evaluate_optimized_out_variable_test.dart
new file mode 100644
index 00000000000..30f5f4c4428
--- /dev/null
+++ b/pkg/vm_service/test/evaluate_optimized_out_variable_test.dart
@@ -0,0 +1,85 @@
+// Copyright (c) 2024, the Dart project authors. Please see the AUTHORS file
+// for details. All rights reserved. Use of this source code is governed by a
+// BSD-style license that can be found in the LICENSE file.
+
+// Regression test for https://dartbug.com/53996.
+
+import 'package:test/test.dart';
+import 'package:vm_service/vm_service.dart';
+
+import 'common/service_test_common.dart';
+import 'common/test_helper.dart';
+
+// AUTOGENERATED START
+//
+// Update these constants by running:
+//
+// dart pkg/vm_service/test/update_line_numbers.dart <test.dart>
+//
+const LINE_A = 27;
+// AUTOGENERATED END
+
+bool debug = false;
+
+bool bar(int i) {
+  if (i == 2) {
+    if (debug) {
+      print('woke up'); // LINE_A
+    }
+    return true;
+  }
+  return false;
+}
+
+void foo() {
+  final List<int> data = [1, 2, 3];
+  for (int i in data) {
+    if (bar(i)) {
+      break;
+    }
+  }
+}
+
+void testeeMain() {
+  // Trigger optimization of [foo].
+  for (int i = 0; i < 20; i++) {
+    foo();
+  }
+  debug = true;
+  foo();
+}
+
+final tests = <IsolateTest>[
+  hasPausedAtStart,
+  setBreakpointAtLine(LINE_A),
+  resumeIsolate,
+  hasStoppedAtBreakpoint,
+  stoppedAtLine(LINE_A),
+  (VmService service, IsolateRef isolateRef) async {
+    final isolateId = isolateRef.id!;
+    try {
+      await service.evaluateInFrame(
+        isolateId,
+        1,
+        'data.length',
+      );
+      fail('Expected evaluateInFrame to throw an RPCError');
+    } on RPCError catch (e) {
+      expect(e.code, RPCErrorKind.kExpressionCompilationError.code);
+      expect(e.message, 'Expression compilation error');
+    }
+  },
+];
+
+void main([args = const <String>[]]) => runIsolateTests(
+      args,
+      tests,
+      'evaluate_optimized_out_variable_test.dart',
+      testeeConcurrent: testeeMain,
+      pauseOnStart: true,
+      extraArgs: const [
+        '--deterministic',
+        '--prune-dead-locals',
+        '--optimization-counter-threshold=10',
+      ],
+    );
diff --git a/runtime/vm/debugger.cc b/runtime/vm/debugger.cc
index 40ae71a74d2..cb2149dd79c 100644
--- a/runtime/vm/debugger.cc
+++ b/runtime/vm/debugger.cc
@@ -1111,7 +1111,8 @@ TypeArgumentsPtr ActivationFrame::BuildParameters(
       type_arguments_available = true;
       type_arguments ^= value.ptr();
     } else if (!name.Equals(Symbols::This()) &&
-               !IsSyntheticVariableName(name)) {
+               !IsSyntheticVariableName(name) &&
+               value.ptr() != Object::optimized_out().ptr()) {
       if (IsPrivateVariableName(name)) {
         name = Symbols::New(Thread::Current(), String::ScrubName(name));
       }
diff --git a/runtime/vm/object.cc b/runtime/vm/object.cc
index f2f07be9b21..17003bb98a2 100644
--- a/runtime/vm/object.cc
+++ b/runtime/vm/object.cc
@@ -4945,6 +4945,12 @@ ObjectPtr Instance::EvaluateCompiledExpression(
 
   const auto& eval_function = Function::Cast(result);
 
+#if defined(DEBUG)
+  for (intptr_t i = 0; i < arguments.Length(); ++i) {
+    ASSERT(arguments.At(i) != Object::optimized_out().ptr());
+  }
+#endif  // defined(DEBUG)
+
   auto& all_arguments = Array::Handle(zone, arguments.ptr());
   if (!eval_function.is_static()) {
     // `this` may be optimized out (e.g. not accessible from breakpoint due to