diff --git a/kubernetes-kit-starter/src/main/java/com/vaadin/kubernetes/starter/sessiontracker/serialization/debug/Job.java b/kubernetes-kit-starter/src/main/java/com/vaadin/kubernetes/starter/sessiontracker/serialization/debug/Job.java
index 4d0d90d..aa74207 100644
--- a/kubernetes-kit-starter/src/main/java/com/vaadin/kubernetes/starter/sessiontracker/serialization/debug/Job.java
+++ b/kubernetes-kit-starter/src/main/java/com/vaadin/kubernetes/starter/sessiontracker/serialization/debug/Job.java
@@ -9,8 +9,10 @@
  */
 package com.vaadin.kubernetes.starter.sessiontracker.serialization.debug;
 
+import java.io.InvalidObjectException;
 import java.io.ObjectStreamClass;
 import java.lang.invoke.SerializedLambda;
+import java.lang.reflect.InvocationTargetException;
 import java.lang.reflect.Method;
 import java.util.ArrayList;
 import java.util.Collections;
@@ -194,10 +196,11 @@ void deserializationFailed(Exception ex) {
         outcome.add(Outcome.DESERIALIZATION_FAILED);
         log(CATEGORY_ERRORS,
                 Outcome.DESERIALIZATION_FAILED.name() + ": " + ex.getMessage());
-        if (ex instanceof ClassCastException
-                && ex.getMessage().contains(SerializedLambda.class.getName())
+        Throwable cause = tryUnwrapLambdaDeserializationCause(ex);
+        if (cause instanceof ClassCastException
+                && cause.getMessage().contains(SerializedLambda.class.getName())
                 && !serializedLambdaMap.isEmpty()) {
-            String targetType = tryDetectClassCastTarget(ex.getMessage());
+            String targetType = tryDetectClassCastTarget(cause.getMessage());
             if (targetType != null) {
                 String bestCandidates = serializedLambdaMap.values().stream()
                         .filter(serializedLambda -> serializedLambda
@@ -223,6 +226,19 @@ void deserializationFailed(Exception ex) {
         }
     }
 
+    // Base on the JDK version, SerializedLambda.readResolve may differently
+    // wrap the cause of error
+    private Throwable tryUnwrapLambdaDeserializationCause(Throwable exception) {
+        Throwable cause = exception;
+        if (cause instanceof InvalidObjectException) {
+            cause = cause.getCause();
+        }
+        if (cause instanceof InvocationTargetException) {
+            cause = cause.getCause();
+        }
+        return cause;
+    }
+
     private Logger getLogger() {
         return LoggerFactory.getLogger(DebugMode.class);
     }
diff --git a/kubernetes-kit-starter/src/test/java/com/vaadin/kubernetes/starter/sessiontracker/serialization/debug/SerializationDebugRequestHandlerTest.java b/kubernetes-kit-starter/src/test/java/com/vaadin/kubernetes/starter/sessiontracker/serialization/debug/SerializationDebugRequestHandlerTest.java
index d7eaaa3..9cdb1ed 100644
--- a/kubernetes-kit-starter/src/test/java/com/vaadin/kubernetes/starter/sessiontracker/serialization/debug/SerializationDebugRequestHandlerTest.java
+++ b/kubernetes-kit-starter/src/test/java/com/vaadin/kubernetes/starter/sessiontracker/serialization/debug/SerializationDebugRequestHandlerTest.java
@@ -1,21 +1,23 @@
 package com.vaadin.kubernetes.starter.sessiontracker.serialization.debug;
 
+import jakarta.servlet.http.HttpServletRequest;
+import jakarta.servlet.http.HttpSession;
+
 import java.io.IOException;
 import java.io.ObjectInputStream;
 import java.io.ObjectOutputStream;
 import java.io.Serializable;
+import java.lang.invoke.SerializedLambda;
 import java.util.ArrayList;
 import java.util.List;
 import java.util.Map;
+import java.util.Objects;
 import java.util.concurrent.atomic.AtomicReference;
 import java.util.stream.Stream;
 
-import jakarta.servlet.http.HttpServletRequest;
-import jakarta.servlet.http.HttpSession;
 import org.assertj.core.api.SoftAssertions;
 import org.assertj.core.data.Index;
 import org.junit.jupiter.api.BeforeEach;
-import org.junit.jupiter.api.Disabled;
 import org.junit.jupiter.api.Test;
 import org.junit.jupiter.api.condition.EnabledIfSystemProperty;
 import org.springframework.mock.web.MockHttpSession;
@@ -314,8 +316,40 @@ void handleRequest_serializationTimeout_timeoutReported() {
     }
 
     @Test
-    @Disabled("Find a way to simulate SerializedLambda ClassCastException")
     void handleRequest_lambdaSelfReferenceClassCast_errorCaught() {
+
+        LambdaDeserializationClassCast holder = new LambdaDeserializationClassCast();
+        httpSession.setAttribute("OBJ1", holder.selfReferenceLambda);
+
+        runDebugTool();
+        Result result = resultHolder.get();
+        assertThat(result.getOutcomes())
+                .containsExactly(Outcome.DESERIALIZATION_FAILED);
+        String unserializableInfo = String.join(System.lineSeparator(),
+                result.getErrors());
+        assertThat(unserializableInfo)
+                .contains("cannot assign instance of "
+                        + SerializedLambda.class.getName())
+                .contains("field "
+                        + LambdaDeserializationClassCast.class.getName()
+                        + ".selfReferenceLambda")
+                .contains("in instance of "
+                        + LambdaDeserializationClassCast.class.getName())
+                .contains(
+                        "SERIALIZED LAMBDA CLASS CAST EXCEPTION BEST CANDIDATES")
+                .contains("SerializedLambda[capturingClass=class "
+                        + LambdaDeserializationClassCast.class.getName());
+    }
+
+    static class LambdaDeserializationClassCast implements Serializable {
+
+        private final Serializable capture = new Serializable() {
+        };
+
+        private final SerializableRunnable selfReferenceLambda = () -> {
+            Objects.requireNonNull(capture);
+        };
+
     }
 
     private void assertDebugToolNotExecuted() {