diff --git a/src/test/kotlin/AdvancedTest.kt b/src/test/kotlin/AdvancedTest.kt
index 423b7e7..cb77b58 100644
--- a/src/test/kotlin/AdvancedTest.kt
+++ b/src/test/kotlin/AdvancedTest.kt
@@ -5,6 +5,7 @@ import com.yhs0602.vm.RegisterValue
 import com.yhs0602.vm.executeMethod
 import java.io.File
 import java.io.PrintStream
+import java.io.Serializable
 import java.nio.file.Paths
 import kotlin.jvm.internal.Intrinsics
 import kotlin.test.BeforeTest
@@ -87,6 +88,26 @@ class AdvancedTest {
         )
     }
 
+    @Test
+    fun TestHardInstanceOf() {
+        testInterpreter(
+            "src/test/resources/advanced/",
+            "com.example.sample",
+            "InstanceOfTestKt",
+            "advancedInstanceOfTest",
+            listOf(
+                GeneralMockedClass(StringBuilder::class.java),
+                GeneralMockedClass(System::class.java),
+                GeneralMockedClass(Intrinsics::class.java),
+                GeneralMockedClass(Object::class.java),
+                GeneralMockedClass(PrintStream::class.java),
+                GeneralMockedClass(File::class.java),
+                GeneralMockedClass(Serializable::class.java),
+                GeneralMockedClass(Comparable::class.java),
+            )
+        )
+    }
+
     @Test
     fun TestStatic() {
         testInterpreter(
diff --git a/src/test/resources/advanced/classes4.dex b/src/test/resources/advanced/classes4.dex
index f74682e..d25f1ed 100644
Binary files a/src/test/resources/advanced/classes4.dex and b/src/test/resources/advanced/classes4.dex differ
diff --git a/src/test/resources/advanced/instanceoftest.kt b/src/test/resources/advanced/instanceoftest.kt
index c86bc48..f12a26a 100644
--- a/src/test/resources/advanced/instanceoftest.kt
+++ b/src/test/resources/advanced/instanceoftest.kt
@@ -1,5 +1,8 @@
 package com.example.sample
 
+import java.io.File
+import java.io.Serializable
+
 open class B
 
 open class C: B()
@@ -78,5 +81,48 @@ fun testInstanceOf() {
     assert((f5 as Any) !is I1)
     assert(f6 is I1)
 
+    println("All tests passed!")
+}
+
+open class HardA: File("")
+
+open class HardB: Serializable
+
+open class HardC: Comparable<HardC> {
+    override fun compareTo(other: HardC): Int {
+        return 0
+    }
+}
+
+class HardD: HardA()
+
+class HardE: HardB()
+
+class HardF: HardC(), Serializable
+
+fun advancedInstanceOfTest() {
+    val a = HardA()
+    val b = HardB()
+    val c = HardC()
+    val d = HardD()
+    val e = HardE()
+    val f = HardF()
+
+    assert(a is File)
+    assert(b is Serializable)
+    assert(c is Comparable<HardC>)
+
+    assert(d is HardA)
+    assert(d is File)
+    assert(d is Serializable)
+    assert(d is Comparable<*>)
+
+    assert(e is Serializable)
+    assert(e is HardB)
+
+    assert(f is Serializable)
+    assert(f is Comparable<HardC>)
+    assert(f is HardC)
+
     println("All tests passed!")
 }
\ No newline at end of file