diff --git a/make/data/hotspot-symbols/symbols-unix b/make/data/hotspot-symbols/symbols-unix
index fbb82a11fac..0ce1483f890 100644
--- a/make/data/hotspot-symbols/symbols-unix
+++ b/make/data/hotspot-symbols/symbols-unix
@@ -224,6 +224,7 @@ JVM_VirtualThreadMount
 JVM_VirtualThreadUnmount
 JVM_VirtualThreadHideFrames
 JVM_VirtualThreadDisableSuspend
+JVM_VirtualThreadWaitForPendingList
 
 # Scoped values
 JVM_EnsureMaterializedForStackWalk_func
diff --git a/src/hotspot/share/include/jvm.h b/src/hotspot/share/include/jvm.h
index 5d6ab27a3a1..b534dc36582 100644
--- a/src/hotspot/share/include/jvm.h
+++ b/src/hotspot/share/include/jvm.h
@@ -1157,6 +1157,9 @@ JVM_VirtualThreadHideFrames(JNIEnv* env, jobject vthread, jboolean hide);
 JNIEXPORT void JNICALL
 JVM_VirtualThreadDisableSuspend(JNIEnv* env, jobject vthread, jboolean enter);
 
+JNIEXPORT jobject JNICALL
+JVM_VirtualThreadWaitForPendingList(JNIEnv* env);
+
 /*
  * Core reflection support.
  */
diff --git a/src/java.base/share/classes/java/lang/VirtualThread.java b/src/java.base/share/classes/java/lang/VirtualThread.java
index 19635db8bbd..4df3b32670c 100644
--- a/src/java.base/share/classes/java/lang/VirtualThread.java
+++ b/src/java.base/share/classes/java/lang/VirtualThread.java
@@ -81,6 +81,7 @@ final class VirtualThread extends BaseVirtualThread {
     private static final long PARK_PERMIT = U.objectFieldOffset(VirtualThread.class, "parkPermit");
     private static final long CARRIER_THREAD = U.objectFieldOffset(VirtualThread.class, "carrierThread");
     private static final long TERMINATION = U.objectFieldOffset(VirtualThread.class, "termination");
+    private static final long ON_WAITING_LIST = U.objectFieldOffset(VirtualThread.class, "onWaitingList");
 
     // scheduler and continuation
     private final Executor scheduler;
@@ -132,6 +133,9 @@ final class VirtualThread extends BaseVirtualThread {
     // Thread.yield
     private static final int YIELDING = 10;
     private static final int YIELDED  = 11;         // unmounted but runnable
+    // monitor enter
+    private static final int BLOCKING   = 12;
+    private static final int BLOCKED    = 13;
 
     private static final int TERMINATED = 99;  // final state
 
@@ -141,12 +145,20 @@ final class VirtualThread extends BaseVirtualThread {
     // parking permit
     private volatile boolean parkPermit;
 
+
+    // unblocked
+    private volatile boolean unblocked;
+
     // carrier thread when mounted, accessed by VM
     private volatile Thread carrierThread;
 
     // termination object when joining, created lazily if needed
     private volatile CountDownLatch termination;
 
+   // Next waiting vthread to unpark()
+    private VirtualThread next;
+    private byte onWaitingList;
+
     /**
      * Returns the continuation scope used for virtual threads.
      */
@@ -499,6 +511,16 @@ private void afterYield() {
             return;
         }
 
+        // blocking on monitorenter
+        if (s == BLOCKING) {
+            setState(BLOCKED);
+            if (unblocked && compareAndSetState(BLOCKED, UNPARKED)) {
+                unblocked = false;
+                submitRunContinuation();
+            }
+            return;
+        }
+
         assert false;
     }
 
@@ -772,6 +794,19 @@ void unpark() {
         }
     }
 
+    /**
+     * Re-enables this virtual thread for scheduling after blocking on monitor enter.
+     * @throws RejectedExecutionException if the scheduler cannot accept a task
+     */
+    private void unblock() {
+        assert !Thread.currentThread().isVirtual();
+        unblocked = true;
+        if (state() == BLOCKED && compareAndSetState(BLOCKED, UNPARKED)) {
+            unblocked = false;
+            submitRunContinuation();
+        }
+    }
+
     /**
      * Attempts to yield the current virtual thread (Thread.yield).
      */
@@ -924,6 +959,7 @@ Thread.State threadState() {
                 }
             case UNPARKED:
             case YIELDED:
+            case BLOCKING:
                 // runnable, not mounted
                 return Thread.State.RUNNABLE;
             case RUNNING:
@@ -952,6 +988,8 @@ Thread.State threadState() {
             case TIMED_PARKED:
             case TIMED_PINNED:
                 return State.TIMED_WAITING;
+            case BLOCKED:
+                return State.BLOCKED;
             case TERMINATED:
                 return Thread.State.TERMINATED;
             default:
@@ -997,7 +1035,7 @@ private StackTraceElement[] tryGetStackTrace() {
             case RUNNING, PINNED, TIMED_PINNED -> {
                 return null;   // mounted
             }
-            case PARKED, TIMED_PARKED -> {
+            case PARKED, BLOCKED, TIMED_PARKED -> {
                 // unmounted, not runnable
             }
             case UNPARKED, YIELDED -> {
@@ -1028,9 +1066,9 @@ private StackTraceElement[] tryGetStackTrace() {
                 // resubmit as task may have run while suspended
                 yield true;
             }
-            case PARKED, TIMED_PARKED -> {
+            case PARKED, BLOCKED, TIMED_PARKED -> {
                 // resubmit if unparked while suspended
-                yield parkPermit && compareAndSetState(initialState, UNPARKED);
+                yield (parkPermit || unblocked) && compareAndSetState(initialState, UNPARKED);
             }
             default -> throw new InternalError();
         };
@@ -1119,6 +1157,16 @@ private void setState(int newValue) {
         state = newValue;  // volatile write
     }
 
+    private VirtualThread next() {
+        return next;
+    }
+
+    private void removeFromWaitingList() {
+        next = null;
+        boolean res = U.compareAndSetByte(this, ON_WAITING_LIST, (byte)0x01, (byte)0x00);
+        assert res;
+    }
+
     private boolean compareAndSetState(int expectedValue, int newValue) {
         return U.compareAndSetInt(this, STATE, expectedValue, newValue);
     }
@@ -1244,4 +1292,28 @@ private static int tracePinningMode() {
         }
         return 0;
     }
+
+    /**
+     * Unblock virtual threads that are ready to scheduled again.
+     */
+    private static void processPendingList() {
+        while (true) {
+            VirtualThread currentWaitingVThread = waitForPendingList();
+            VirtualThread nextWaitingVThread = null;
+            while (currentWaitingVThread != null) {
+                nextWaitingVThread = currentWaitingVThread.next();
+                currentWaitingVThread.removeFromWaitingList();
+                currentWaitingVThread.unpark();
+                currentWaitingVThread = nextWaitingVThread;
+            }
+        }
+    }
+
+    private static native VirtualThread waitForPendingList();
+
+    static {
+        var unblocker = InnocuousThread.newThread("VirtualThread-unblocker",
+                VirtualThread::processPendingList);
+        unblocker.start();
+    }
 }
diff --git a/src/java.base/share/native/libjava/VirtualThread.c b/src/java.base/share/native/libjava/VirtualThread.c
index 94dbe0b7e37..1ef29270ddd 100644
--- a/src/java.base/share/native/libjava/VirtualThread.c
+++ b/src/java.base/share/native/libjava/VirtualThread.c
@@ -38,6 +38,7 @@ static JNINativeMethod methods[] = {
     { "notifyJvmtiUnmount",        "(Z)V", (void *)&JVM_VirtualThreadUnmount },
     { "notifyJvmtiHideFrames",     "(Z)V", (void *)&JVM_VirtualThreadHideFrames },
     { "notifyJvmtiDisableSuspend", "(Z)V", (void *)&JVM_VirtualThreadDisableSuspend },
+    { "waitForPendingList",      "()" VIRTUAL_THREAD, (void *)&JVM_VirtualThreadWaitForPendingList },
 };
 
 JNIEXPORT void JNICALL
diff --git a/test/jdk/java/lang/Thread/virtual/MonitorsTest.java b/test/jdk/java/lang/Thread/virtual/MonitorsTest.java
new file mode 100644
index 00000000000..23391a3918c
--- /dev/null
+++ b/test/jdk/java/lang/Thread/virtual/MonitorsTest.java
@@ -0,0 +1,408 @@
+/*
+ * Copyright (c) 2023, Oracle and/or its affiliates. All rights reserved.
+ * DO NOT ALTER OR REMOVE COPYRIGHT NOTICES OR THIS FILE HEADER.
+ *
+ * This code is free software; you can redistribute it and/or modify it
+ * under the terms of the GNU General Public License version 2 only, as
+ * published by the Free Software Foundation.
+ *
+ * This code is distributed in the hope that it will be useful, but WITHOUT
+ * ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or
+ * FITNESS FOR A PARTICULAR PURPOSE.  See the GNU General Public License
+ * version 2 for more details (a copy is included in the LICENSE file that
+ * accompanied this code).
+ *
+ * You should have received a copy of the GNU General Public License version
+ * 2 along with this work; if not, write to the Free Software Foundation,
+ * Inc., 51 Franklin St, Fifth Floor, Boston, MA 02110-1301 USA.
+ *
+ * Please contact Oracle, 500 Oracle Parkway, Redwood Shores, CA 94065 USA
+ * or visit www.oracle.com if you need additional information or have any
+ * questions.
+ */
+
+/**
+ * @test
+ * @summary Test virtual threads using synchronized
+ * @library /test/lib
+ * @modules java.base/java.lang:+open
+ *
+ * @run junit/othervm/timeout=10 -Xint MonitorsTest
+ * @run junit/othervm/timeout=50 -Xcomp MonitorsTest
+ * @run junit/othervm/timeout=50 MonitorsTest
+ * @run junit/othervm/timeout=50 -XX:+FullGCALot -XX:FullGCALotInterval=1000 MonitorsTest
+ */
+
+import java.util.concurrent.atomic.AtomicInteger;
+import java.util.concurrent.*;
+
+import org.junit.jupiter.api.Test;
+import static org.junit.jupiter.api.Assertions.*;
+
+class MonitorsTest {
+    final int CARRIER_COUNT = 8;
+    ExecutorService scheduler = Executors.newFixedThreadPool(CARRIER_COUNT);
+
+    static final Object globalLock = new Object();
+    static volatile boolean finish = false;
+    static volatile int counter = 0;
+
+    /////////////////////////////////////////////////////////////////////
+    //////////////////////////// BASIC TESTS ////////////////////////////
+    /////////////////////////////////////////////////////////////////////
+
+    static final Runnable FOO = () -> {
+        Object lock = new Object();
+        synchronized(lock) {
+            while(!finish) {
+                Thread.yield();
+            }
+        }
+        System.out.println("Exiting FOO from thread " + Thread.currentThread().getName());
+    };
+
+    static final Runnable BAR = () -> {
+        synchronized(globalLock) {
+            counter++;
+        }
+        System.out.println("Exiting BAR from thread " + Thread.currentThread().getName());
+    };
+
+    /**
+     *  Test yield while holding monitor.
+     */
+    @Test
+    void testBasic() throws Exception {
+        final int VT_COUNT = CARRIER_COUNT;
+
+        // Create first batch of VT threads.
+        Thread firstBatch[] = new Thread[VT_COUNT];
+        for (int i = 0; i < VT_COUNT; i++) {
+            firstBatch[i] = ThreadBuilders.virtualThreadBuilder(scheduler).name("FirstBatchVT-" + i).start(FOO);
+        }
+
+        // Give time for all threads to reach Thread.yield
+        Thread.sleep(1000);
+
+        // Create second batch of VT threads.
+        Thread secondBatch[] = new Thread[VT_COUNT];
+        for (int i = 0; i < VT_COUNT; i++) {
+            secondBatch[i] = ThreadBuilders.virtualThreadBuilder(scheduler).name("SecondBatchVT-" + i).start(BAR);
+        }
+
+        while(counter != VT_COUNT) {}
+
+        finish = true;
+
+        for (int i = 0; i < VT_COUNT; i++) {
+            firstBatch[i].join();
+        }
+        for (int i = 0; i < VT_COUNT; i++) {
+            secondBatch[i].join();
+        }
+    }
+
+    static final Runnable BAR2 = () -> {
+        synchronized(globalLock) {
+            counter++;
+        }
+        recursive2(10);
+        System.out.println("Exiting BAR2 from thread " + Thread.currentThread().getName() + "with counter=" + counter);
+    };
+
+    static void recursive2(int count) {
+        synchronized(Thread.currentThread()) {
+            if (count > 0) {
+                recursive2(count - 1);
+            } else {
+                synchronized(globalLock) {
+                    counter++;
+                    Thread.yield();
+                }
+            }
+        }
+    }
+
+    /**
+     *  Test yield while holding monitor with recursive locking.
+     */
+    @Test
+    void testRecursive() throws Exception {
+        final int VT_COUNT = CARRIER_COUNT;
+        counter = 0;
+        finish = false;
+
+        // Create first batch of VT threads.
+        Thread firstBatch[] = new Thread[VT_COUNT];
+        for (int i = 0; i < VT_COUNT; i++) {
+            firstBatch[i] = ThreadBuilders.virtualThreadBuilder(scheduler).name("FirstBatchVT-" + i).start(FOO);
+        }
+
+        // Give time for all threads to reach Thread.yield
+        Thread.sleep(1000);
+
+        // Create second batch of VT threads.
+        Thread secondBatch[] = new Thread[VT_COUNT];
+        for (int i = 0; i < VT_COUNT; i++) {
+            secondBatch[i] = ThreadBuilders.virtualThreadBuilder(scheduler).name("SecondBatchVT-" + i).start(BAR2);
+        }
+
+        while(counter != 2*VT_COUNT) {}
+
+        finish = true;
+
+        for (int i = 0; i < VT_COUNT; i++) {
+            firstBatch[i].join();
+        }
+        for (int i = 0; i < VT_COUNT; i++) {
+            secondBatch[i].join();
+        }
+    }
+
+    static final Runnable FOO3 = () -> {
+        synchronized(globalLock) {
+            while(!finish) {
+                Thread.yield();
+            }
+        }
+        System.out.println("Exiting FOO3 from thread " + Thread.currentThread().getName());
+    };
+
+    /**
+     *  Test contention on monitorenter.
+     */
+    @Test
+    void testContention() throws Exception {
+        final int VT_COUNT = CARRIER_COUNT * 8;
+        counter = 0;
+        finish = false;
+
+        // Create batch of VT threads.
+        Thread batch[] = new Thread[VT_COUNT];
+        for (int i = 0; i < VT_COUNT; i++) {
+            batch[i] = ThreadBuilders.virtualThreadBuilder(scheduler).name("BatchVT-" + i).start(FOO3);
+        }
+
+        // Give time for all threads to reach synchronized(globalLock)
+        Thread.sleep(2000);
+
+        finish = true;
+
+        for (int i = 0; i < VT_COUNT; i++) {
+            batch[i].join();
+        }
+    }
+
+    /////////////////////////////////////////////////////////////////////
+    //////////////////////////// MAIN TESTS /////////////////////////////
+    /////////////////////////////////////////////////////////////////////
+
+    static final int MONITORS_CNT = 12;
+    static Object[] globalLockArray;
+    static AtomicInteger workerCount = new AtomicInteger(0);
+
+    static void recursive4_1(int depth, int lockNumber) {
+        if (depth > 0) {
+            recursive4_1(depth - 1, lockNumber);
+        } else {
+            if (Math.random() < 0.5) {
+                Thread.yield();
+            }
+            recursive4_2(lockNumber);
+        }
+    }
+
+    static void recursive4_2(int lockNumber) {
+        if (lockNumber + 2 <= MONITORS_CNT - 1) {
+            lockNumber += 2;
+            synchronized(globalLockArray[lockNumber]) {
+                Thread.yield();
+                recursive4_2(lockNumber);
+            }
+        }
+    }
+
+    static final Runnable FOO4 = () -> {
+        while (!finish) {
+            int lockNumber = ThreadLocalRandom.current().nextInt(0, MONITORS_CNT - 1);
+            synchronized(globalLockArray[lockNumber]) {
+                recursive4_1(lockNumber, lockNumber);
+            }
+        }
+        workerCount.getAndIncrement();
+        System.out.println("Exiting FOO4 from thread " + Thread.currentThread().getName());
+    };
+
+    /**
+     *  Test contention on monitorenter with extra monitors on stack shared by all threads.
+     */
+    @Test
+    void testContentionMultipleMonitors() throws Exception {
+        final int VT_COUNT = CARRIER_COUNT * 8;
+        workerCount.getAndSet(0);
+        finish = false;
+
+        globalLockArray = new Object[MONITORS_CNT];
+        for (int i = 0; i < MONITORS_CNT; i++) {
+            globalLockArray[i] = new Object();
+        }
+
+        Thread batch[] = new Thread[VT_COUNT];
+        for (int i = 0; i < VT_COUNT; i++) {
+            batch[i] = ThreadBuilders.virtualThreadBuilder(scheduler).name("BatchVT-" + i).start(FOO4);
+        }
+
+        Thread.sleep(10000);
+        finish = true;
+
+        for (int i = 0; i < VT_COUNT; i++) {
+            batch[i].join();
+        }
+
+        if (workerCount.get() != VT_COUNT) {
+            throw new RuntimeException("testContentionMultipleMonitors2 failed. Expected " + VT_COUNT + "but found " + workerCount.get());
+        }
+    }
+
+
+    static void recursive5_1(int depth, int lockNumber, Object[] myLockArray) {
+        if (depth > 0) {
+            recursive5_1(depth - 1, lockNumber, myLockArray);
+        } else {
+            if (Math.random() < 0.5) {
+                Thread.yield();
+            }
+            recursive5_2(lockNumber, myLockArray);
+        }
+    }
+
+    static void recursive5_2(int lockNumber, Object[] myLockArray) {
+        if (lockNumber + 2 <= MONITORS_CNT - 1) {
+            lockNumber += 2;
+            synchronized (myLockArray[lockNumber]) {
+                if (Math.random() < 0.5) {
+                    Thread.yield();
+                }
+                synchronized (globalLockArray[lockNumber]) {
+                    Thread.yield();
+                    recursive5_2(lockNumber, myLockArray);
+                }
+            }
+        }
+    }
+
+    static final Runnable FOO5 = () -> {
+        Object[] myLockArray = new Object[MONITORS_CNT];
+        for (int i = 0; i < MONITORS_CNT; i++) {
+            myLockArray[i] = new Object();
+        }
+
+        while (!finish) {
+            int lockNumber = ThreadLocalRandom.current().nextInt(0, MONITORS_CNT - 1);
+            synchronized (myLockArray[lockNumber]) {
+                synchronized (globalLockArray[lockNumber]) {
+                    recursive5_1(lockNumber, lockNumber, myLockArray);
+                }
+            }
+        }
+        workerCount.getAndIncrement();
+        System.out.println("Exiting FOO5 from thread " + Thread.currentThread().getName());
+    };
+
+    /**
+     *  Test contention on monitorenter with extra monitors on stack both local only and shared by all threads.
+     */
+    @Test
+    void testContentionMultipleMonitors2() throws Exception {
+        final int VT_COUNT = CARRIER_COUNT * 8;
+        workerCount.getAndSet(0);
+        finish = false;
+
+        globalLockArray = new Object[MONITORS_CNT];
+        for (int i = 0; i < MONITORS_CNT; i++) {
+            globalLockArray[i] = new Object();
+        }
+
+        // Create batch of VT threads.
+        Thread batch[] = new Thread[VT_COUNT];
+        for (int i = 0; i < VT_COUNT; i++) {
+            //Thread.ofVirtual().name("FirstBatchVT-" + i).start(FOO);
+            batch[i] = ThreadBuilders.virtualThreadBuilder(scheduler).name("BatchVT-" + i).start(FOO5);
+        }
+
+        Thread.sleep(10000);
+
+        finish = true;
+
+        for (int i = 0; i < VT_COUNT; i++) {
+            batch[i].join();
+        }
+
+        if (workerCount.get() != VT_COUNT) {
+            throw new RuntimeException("testContentionMultipleMonitors2 failed. Expected " + VT_COUNT + "but found " + workerCount.get());
+        }
+    }
+
+    static synchronized void recursive6(int depth, Object myLock) {
+        if (depth > 0) {
+            recursive6(depth - 1, myLock);
+        } else {
+            if (Math.random() < 0.5) {
+                Thread.yield();
+            } else {
+                synchronized (myLock) {
+                    Thread.yield();
+                }
+            }
+        }
+    }
+
+    static final Runnable FOO6 = () -> {
+        Object myLock = new Object();
+
+        while (!finish) {
+            int lockNumber = ThreadLocalRandom.current().nextInt(0, MONITORS_CNT - 1);
+            synchronized (myLock) {
+                synchronized (globalLockArray[lockNumber]) {
+                    recursive6(lockNumber, myLock);
+                }
+            }
+        }
+        workerCount.getAndIncrement();
+        System.out.println("Exiting FOO5 from thread " + Thread.currentThread().getName());
+    };
+
+    /**
+     *  Test contention on monitorenter with synchronized methods.
+     */
+    @Test
+    void testContentionMultipleMonitors3() throws Exception {
+        final int VT_COUNT = CARRIER_COUNT * 8;
+        workerCount.getAndSet(0);
+        finish = false;
+
+
+        globalLockArray = new Object[MONITORS_CNT];
+        for (int i = 0; i < MONITORS_CNT; i++) {
+            globalLockArray[i] = new Object();
+        }
+
+        // Create batch of VT threads.
+        Thread batch[] = new Thread[VT_COUNT];
+        for (int i = 0; i < VT_COUNT; i++) {
+            batch[i] = ThreadBuilders.virtualThreadBuilder(scheduler).name("BatchVT-" + i).start(FOO6);
+        }
+
+        Thread.sleep(10000);
+
+        finish = true;
+
+        for (int i = 0; i < VT_COUNT; i++) {
+            batch[i].join();
+        }
+
+        if (workerCount.get() != VT_COUNT) {
+            throw new RuntimeException("testContentionMultipleMonitors2 failed. Expected " + VT_COUNT + "but found " + workerCount.get());
+        }
+    }
+}
\ No newline at end of file