diff --git a/src/libraries/Common/src/Interop/Windows/Kernel32/Interop.Threading.cs b/src/libraries/Common/src/Interop/Windows/Kernel32/Interop.Threading.cs
index 14863bf1e4f749..b323cacc6bcaee 100644
--- a/src/libraries/Common/src/Interop/Windows/Kernel32/Interop.Threading.cs
+++ b/src/libraries/Common/src/Interop/Windows/Kernel32/Interop.Threading.cs
@@ -10,6 +10,7 @@ internal static partial class Interop
     internal static partial class Kernel32
     {
         internal const int WAIT_FAILED = unchecked((int)0xFFFFFFFF);
+        internal const int WAIT_IO_COMPLETION = 0x000000C0;
 
         [LibraryImport(Libraries.Kernel32)]
         internal static partial uint WaitForMultipleObjectsEx(uint nCount, IntPtr lpHandles, BOOL bWaitAll, uint dwMilliseconds, BOOL bAlertable);
@@ -17,6 +18,9 @@ internal static partial class Kernel32
         [LibraryImport(Libraries.Kernel32)]
         internal static partial uint WaitForSingleObject(IntPtr hHandle, uint dwMilliseconds);
 
+        [LibraryImport(Libraries.Kernel32)]
+        internal static partial uint WaitForSingleObjectEx(IntPtr hHandle, uint dwMilliseconds, BOOL bAlertable);
+
         [LibraryImport(Libraries.Kernel32)]
         internal static partial uint SignalObjectAndWait(IntPtr hObjectToSignal, IntPtr hObjectToWaitOn, uint dwMilliseconds, BOOL bAlertable);
 
diff --git a/src/libraries/System.Private.CoreLib/src/System/Threading/WaitHandle.Windows.cs b/src/libraries/System.Private.CoreLib/src/System/Threading/WaitHandle.Windows.cs
index d4d01971437637..26ab6b4278b2bf 100644
--- a/src/libraries/System.Private.CoreLib/src/System/Threading/WaitHandle.Windows.cs
+++ b/src/libraries/System.Private.CoreLib/src/System/Threading/WaitHandle.Windows.cs
@@ -49,20 +49,46 @@ private static unsafe int WaitForMultipleObjectsIgnoringSyncContext(IntPtr* pHan
             Thread currentThread = Thread.CurrentThread;
             currentThread.SetWaitSleepJoinState();
 
-#if NATIVEAOT
-            int result;
-            if (reentrantWait)
+            long startTime = 0;
+            if (millisecondsTimeout != -1)
             {
-                Debug.Assert(!waitAll);
-                result = RuntimeImports.RhCompatibleReentrantWaitAny(false, millisecondsTimeout, numHandles, pHandles);
+                startTime = Environment.TickCount64;
             }
-            else
+
+            int result;
+            while (true)
             {
-                result = (int)Interop.Kernel32.WaitForMultipleObjectsEx((uint)numHandles, (IntPtr)pHandles, waitAll ? Interop.BOOL.TRUE : Interop.BOOL.FALSE, (uint)millisecondsTimeout, Interop.BOOL.FALSE);
-            }
+#if NATIVEAOT
+                if (reentrantWait)
+                {
+                    Debug.Assert(!waitAll);
+                    result = RuntimeImports.RhCompatibleReentrantWaitAny(true, millisecondsTimeout, numHandles, pHandles);
+                }
+                else
+                {
+                    result = (int)Interop.Kernel32.WaitForMultipleObjectsEx((uint)numHandles, (IntPtr)pHandles, waitAll ? Interop.BOOL.TRUE : Interop.BOOL.FALSE, (uint)millisecondsTimeout, Interop.BOOL.TRUE);
+                }
 #else
-            int result = (int)Interop.Kernel32.WaitForMultipleObjectsEx((uint)numHandles, (IntPtr)pHandles, waitAll ? Interop.BOOL.TRUE : Interop.BOOL.FALSE, (uint)millisecondsTimeout, Interop.BOOL.FALSE);
+                result = (int)Interop.Kernel32.WaitForMultipleObjectsEx((uint)numHandles, (IntPtr)pHandles, waitAll ? Interop.BOOL.TRUE : Interop.BOOL.FALSE, (uint)millisecondsTimeout, Interop.BOOL.TRUE);
 #endif
+
+                if (result != Interop.Kernel32.WAIT_IO_COMPLETION)
+                    break;
+
+                // Handle APC completion by adjusting timeout and retrying
+                if (millisecondsTimeout != -1)
+                {
+                    long currentTime = Environment.TickCount64;
+                    long elapsed = currentTime - startTime;
+                    if (elapsed >= millisecondsTimeout)
+                    {
+                        result = Interop.Kernel32.WAIT_TIMEOUT;
+                        break;
+                    }
+                    millisecondsTimeout -= (int)elapsed;
+                    startTime = currentTime;
+                }
+            }
             currentThread.ClearWaitSleepJoinState();
 
             if (result == Interop.Kernel32.WAIT_FAILED)
@@ -102,8 +128,35 @@ private static int SignalAndWaitCore(IntPtr handleToSignal, IntPtr handleToWaitO
         {
             Debug.Assert(millisecondsTimeout >= -1);
 
-            int ret = (int)Interop.Kernel32.SignalObjectAndWait(handleToSignal, handleToWaitOn, (uint)millisecondsTimeout, Interop.BOOL.FALSE);
+            long startTime = 0;
+            if (millisecondsTimeout != -1)
+            {
+                startTime = Environment.TickCount64;
+            }
+
+            // Signal the object and wait for the first time
+            int ret = (int)Interop.Kernel32.SignalObjectAndWait(handleToSignal, handleToWaitOn, (uint)millisecondsTimeout, Interop.BOOL.TRUE);
+
+            // Handle APC completion by retrying with WaitForSingleObjectEx (without signaling again)
+            while (ret == Interop.Kernel32.WAIT_IO_COMPLETION)
+            {
+                if (millisecondsTimeout != -1)
+                {
+                    long currentTime = Environment.TickCount64;
+                    long elapsed = currentTime - startTime;
 
+                    if (elapsed >= millisecondsTimeout)
+                    {
+                        ret = Interop.Kernel32.WAIT_TIMEOUT;
+                        break;
+                    }
+                    millisecondsTimeout -= (int)elapsed;
+                    startTime = currentTime;
+                }
+
+                // For retries, only wait on the handle (don't signal again)
+                ret = (int)Interop.Kernel32.WaitForSingleObjectEx(handleToWaitOn, (uint)millisecondsTimeout, Interop.BOOL.TRUE);
+            }
             if (ret == Interop.Kernel32.WAIT_FAILED)
             {
                 ThrowWaitFailedException(Interop.Kernel32.GetLastError());
diff --git a/src/tests/baseservices/threading/regressions/115178/115178.cs b/src/tests/baseservices/threading/regressions/115178/115178.cs
index 5a9fdd46265c4d..34aba004040a9d 100644
--- a/src/tests/baseservices/threading/regressions/115178/115178.cs
+++ b/src/tests/baseservices/threading/regressions/115178/115178.cs
@@ -284,12 +284,17 @@ private static void RunTestInterruptInfiniteWait()
     }
 
     [ConditionalFact(typeof(TestLibrary.Utilities), nameof(TestLibrary.Utilities.IsWindows))]
-    [ActiveIssue("https://github.com/dotnet/runtime/issues/118233", typeof(TestLibrary.Utilities), nameof(TestLibrary.Utilities.IsNativeAot))]
     public static int TestEntryPoint()
     {
         RunTestUsingInfiniteWait();
         RunTestUsingTimedWait();
-        RunTestInterruptInfiniteWait();
+
+        // Thread.Interrupt is not implemented on NativeAOT - https://github.com/dotnet/runtime/issues/69919
+        if (!TestLibrary.Utilities.IsNativeAot)
+        {
+            RunTestInterruptInfiniteWait();
+        }
+
         return result;
     }
 }