diff --git a/idea/jvm-debugger/jvm-debugger-evaluation/src/org/jetbrains/kotlin/idea/debugger/evaluate/classLoading/ClassLoadingAdapter.kt b/idea/jvm-debugger/jvm-debugger-evaluation/src/org/jetbrains/kotlin/idea/debugger/evaluate/classLoading/ClassLoadingAdapter.kt
index 99559db3972..1c365729e67 100644
--- a/idea/jvm-debugger/jvm-debugger-evaluation/src/org/jetbrains/kotlin/idea/debugger/evaluate/classLoading/ClassLoadingAdapter.kt
+++ b/idea/jvm-debugger/jvm-debugger-evaluation/src/org/jetbrains/kotlin/idea/debugger/evaluate/classLoading/ClassLoadingAdapter.kt
@@ -20,6 +20,7 @@ import com.sun.jdi.ArrayReference
 import com.sun.jdi.ArrayType
 import com.sun.jdi.ClassLoaderReference
 import com.sun.jdi.Value
+import jdk.internal.org.objectweb.asm.Opcodes
 import org.jetbrains.kotlin.idea.debugger.evaluate.ExecutionContext
 import org.jetbrains.org.objectweb.asm.ClassReader
 import org.jetbrains.org.objectweb.asm.Label
@@ -63,6 +64,7 @@ interface ClassLoadingAdapter {
 
         private fun analyzeClass(classToLoad: ClassToLoad, info: ClassInfoForEvaluator): ClassInfoForEvaluator {
             val classNode = ClassNode().apply { ClassReader(classToLoad.bytes).accept(this, 0) }
+
             val methodToRun = classNode.methods.single { it.name == GENERATED_FUNCTION_NAME }
 
             val visitedLabels = hashSetOf<Label>()
@@ -78,6 +80,11 @@ interface ClassLoadingAdapter {
                     is TableSwitchInsnNode, is LookupSwitchInsnNode -> {
                         return info.copy(containsCodeUnsupportedInEval4J = true)
                     }
+                    is InsnNode -> {
+                        if (insn.opcode == Opcodes.MONITORENTER || insn.opcode == Opcodes.MONITOREXIT) {
+                            return info.copy(containsCodeUnsupportedInEval4J = true)
+                        }
+                    }
                 }
 
                 val nextInsn = insn.next ?: return info
diff --git a/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/synchronizedBlock.kt b/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/synchronizedBlock.kt
new file mode 100644
index 00000000000..6c69f9ba0ec
--- /dev/null
+++ b/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/synchronizedBlock.kt
@@ -0,0 +1,9 @@
+package synchronizedBlock
+
+fun main() {
+    //Breakpoint!
+    val a = 5
+}
+
+// EXPRESSION: synchronized(Any()) { "foo" }
+// RESULT: "foo": Ljava/lang/String;
\ No newline at end of file
diff --git a/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/synchronizedBlock.kt.fragment b/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/synchronizedBlock.kt.fragment
new file mode 100644
index 00000000000..11496d9412b
--- /dev/null
+++ b/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/synchronizedBlock.kt.fragment
@@ -0,0 +1,10 @@
+class Foo {
+    @Synchronized
+    fun foo(): Int {
+        return 5
+    }
+}
+
+Foo().foo()
+
+// RESULT: 5: I
\ No newline at end of file
diff --git a/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/synchronizedBlock.out b/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/synchronizedBlock.out
new file mode 100644
index 00000000000..ba1e0bea772
--- /dev/null
+++ b/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/synchronizedBlock.out
@@ -0,0 +1,18 @@
+LineBreakpoint created at synchronizedBlock.kt:5
+Run Java
+Connected to the target VM
+synchronizedBlock.kt:5
+Compile bytecode for synchronized(Any()) { "foo" }
+Compile bytecode for class Foo {
+    @Synchronized
+    fun foo(): Int {
+        return 5
+    }
+}
+
+Foo().foo()
+
+// RESULT: 5: I
+Disconnected from the target VM
+
+Process finished with exit code 0
diff --git a/idea/tests/org/jetbrains/kotlin/idea/debugger/evaluate/KotlinEvaluateExpressionTestGenerated.java b/idea/tests/org/jetbrains/kotlin/idea/debugger/evaluate/KotlinEvaluateExpressionTestGenerated.java
index 335a58e76d7..9ec4c25514a 100644
--- a/idea/tests/org/jetbrains/kotlin/idea/debugger/evaluate/KotlinEvaluateExpressionTestGenerated.java
+++ b/idea/tests/org/jetbrains/kotlin/idea/debugger/evaluate/KotlinEvaluateExpressionTestGenerated.java
@@ -391,6 +391,11 @@ public class KotlinEvaluateExpressionTestGenerated extends AbstractKotlinEvaluat
             runTest("idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/stdlib.kt");
         }
 
+        @TestMetadata("synchronizedBlock.kt")
+        public void testSynchronizedBlock() throws Exception {
+            runTest("idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/synchronizedBlock.kt");
+        }
+
         @TestMetadata("typeParameterRef.kt")
         public void testTypeParameterRef() throws Exception {
             runTest("idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/typeParameterRef.kt");