diff --git a/src/hotspot/os/windows/attachListener_windows.cpp b/src/hotspot/os/windows/attachListener_windows.cpp
index da3b6c56739f0..7e455cf0a49f2 100644
--- a/src/hotspot/os/windows/attachListener_windows.cpp
+++ b/src/hotspot/os/windows/attachListener_windows.cpp
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2005, 2023, Oracle and/or its affiliates. All rights reserved.
+ * Copyright (c) 2005, 2024, 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
@@ -248,10 +248,13 @@ Win32AttachOperation* Win32AttachListener::dequeue() {
     DWORD res = ::WaitForSingleObject(enqueued_ops_semaphore(), INFINITE);
     // returning from WaitForSingleObject will have decreased
     // the current count of the semaphore by 1.
-    guarantee(res == WAIT_OBJECT_0, "wait failed");
+    guarantee(res != WAIT_FAILED,   "WaitForSingleObject failed with error code: %lu", GetLastError());
+    guarantee(res == WAIT_OBJECT_0, "WaitForSingleObject failed with return value: %lu", res);
 
     res = ::WaitForSingleObject(mutex(), INFINITE);
-    guarantee(res == WAIT_OBJECT_0, "wait failed");
+    guarantee(res != WAIT_FAILED,   "WaitForSingleObject failed with error code: %lu", GetLastError());
+    guarantee(res == WAIT_OBJECT_0, "WaitForSingleObject failed with return value: %lu", res);
+
 
     Win32AttachOperation* op = head();
     if (op != nullptr) {
@@ -338,6 +341,9 @@ void Win32AttachOperation::complete(jint result, bufferedStream* result_stream)
   }
 
   DWORD res = ::WaitForSingleObject(Win32AttachListener::mutex(), INFINITE);
+  assert(res != WAIT_FAILED,   "WaitForSingleObject failed with error code: %lu", GetLastError());
+  assert(res == WAIT_OBJECT_0, "WaitForSingleObject failed with return value: %lu", res);
+
   if (res == WAIT_OBJECT_0) {
 
     // put the operation back on the available list
diff --git a/src/hotspot/os/windows/os_windows.cpp b/src/hotspot/os/windows/os_windows.cpp
index 1b5c7850bf23f..1d1c30405262e 100644
--- a/src/hotspot/os/windows/os_windows.cpp
+++ b/src/hotspot/os/windows/os_windows.cpp
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 1997, 2023, Oracle and/or its affiliates. All rights reserved.
+ * Copyright (c) 1997, 2024, 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
@@ -5354,7 +5354,8 @@ int PlatformEvent::park(jlong Millis) {
       phri = new HighResolutionInterval(prd);
     }
     rv = ::WaitForSingleObject(_ParkHandle, prd);
-    assert(rv == WAIT_OBJECT_0 || rv == WAIT_TIMEOUT, "WaitForSingleObject failed");
+    assert(rv != WAIT_FAILED,   "WaitForSingleObject failed with error code: %lu", GetLastError());
+    assert(rv == WAIT_OBJECT_0 || rv == WAIT_TIMEOUT, "WaitForSingleObject failed with return value: %lu", rv);
     if (rv == WAIT_TIMEOUT) {
       Millis -= prd;
     }
@@ -5393,7 +5394,8 @@ void PlatformEvent::park() {
   // spin attempts by this thread.
   while (_Event < 0) {
     DWORD rv = ::WaitForSingleObject(_ParkHandle, INFINITE);
-    assert(rv == WAIT_OBJECT_0, "WaitForSingleObject failed");
+    assert(rv != WAIT_FAILED,   "WaitForSingleObject failed with error code: %lu", GetLastError());
+    assert(rv == WAIT_OBJECT_0, "WaitForSingleObject failed with return value: %lu", rv);
   }
 
   // Usually we'll find _Event == 0 at this point, but as
@@ -5456,16 +5458,25 @@ void Parker::park(bool isAbsolute, jlong time) {
   JavaThread* thread = JavaThread::current();
 
   // Don't wait if interrupted or already triggered
-  if (thread->is_interrupted(false) ||
-      WaitForSingleObject(_ParkHandle, 0) == WAIT_OBJECT_0) {
+  if (thread->is_interrupted(false)) {
     ResetEvent(_ParkHandle);
     return;
   } else {
-    ThreadBlockInVM tbivm(thread);
-    OSThreadWaitState osts(thread->osthread(), false /* not Object.wait() */);
+    DWORD rv = WaitForSingleObject(_ParkHandle, 0);
+    assert(rv != WAIT_FAILED,   "WaitForSingleObject failed with error code: %lu", GetLastError());
+    assert(rv == WAIT_OBJECT_0 || rv == WAIT_TIMEOUT, "WaitForSingleObject failed with return value: %lu", rv);
+    if (rv == WAIT_OBJECT_0) {
+      ResetEvent(_ParkHandle);
+      return;
+    } else {
+      ThreadBlockInVM tbivm(thread);
+      OSThreadWaitState osts(thread->osthread(), false /* not Object.wait() */);
 
-    WaitForSingleObject(_ParkHandle, time);
-    ResetEvent(_ParkHandle);
+      rv = WaitForSingleObject(_ParkHandle, time);
+      assert(rv != WAIT_FAILED,   "WaitForSingleObject failed with error code: %lu", GetLastError());
+      assert(rv == WAIT_OBJECT_0 || rv == WAIT_TIMEOUT, "WaitForSingleObject failed with return value: %lu", rv);
+      ResetEvent(_ParkHandle);
+    }
   }
 }
 
@@ -5541,7 +5552,9 @@ int os::fork_and_exec(const char* cmd) {
 
   if (rslt) {
     // Wait until child process exits.
-    WaitForSingleObject(pi.hProcess, INFINITE);
+    DWORD rv = WaitForSingleObject(pi.hProcess, INFINITE);
+    assert(rv != WAIT_FAILED,   "WaitForSingleObject failed with error code: %lu", GetLastError());
+    assert(rv == WAIT_OBJECT_0, "WaitForSingleObject failed with return value: %lu", rv);
 
     GetExitCodeProcess(pi.hProcess, &exit_code);
 
diff --git a/src/hotspot/os/windows/threadCritical_windows.cpp b/src/hotspot/os/windows/threadCritical_windows.cpp
index f781a4224849b..c85143f80930d 100644
--- a/src/hotspot/os/windows/threadCritical_windows.cpp
+++ b/src/hotspot/os/windows/threadCritical_windows.cpp
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2001, 2023, Oracle and/or its affiliates. All rights reserved.
+ * Copyright (c) 2001, 2024, 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
@@ -64,7 +64,8 @@ ThreadCritical::ThreadCritical() {
   if (lock_owner != current_thread) {
     // Grab the lock before doing anything.
     DWORD ret = WaitForSingleObject(lock_event,  INFINITE);
-    assert(ret == WAIT_OBJECT_0, "unexpected return value from WaitForSingleObject");
+    assert(ret != WAIT_FAILED,   "WaitForSingleObject failed with error code: %lu", GetLastError());
+    assert(ret == WAIT_OBJECT_0, "WaitForSingleObject failed with return value: %lu", ret);
     lock_owner = current_thread;
   }
   // Atomicity isn't required. Bump the recursion count.