diff --git a/src/System.Private.Windows.Core/src/System/Private/Windows/Ole/ClipboardConstants.cs b/src/System.Private.Windows.Core/src/System/Private/Windows/Ole/ClipboardConstants.cs
new file mode 100644
index 00000000000..81c5c4aea44
--- /dev/null
+++ b/src/System.Private.Windows.Core/src/System/Private/Windows/Ole/ClipboardConstants.cs
@@ -0,0 +1,17 @@
+// Licensed to the .NET Foundation under one or more agreements.
+// The .NET Foundation licenses this file to you under the MIT license.
+
+namespace System.Private.Windows.Ole;
+
+internal static class ClipboardConstants
+{
+    /// <summary>
+    ///  The number of times to retry OLE clipboard operations.
+    /// </summary>
+    internal const int OleRetryCount = 10;
+
+    /// <summary>
+    ///  The amount of time in milliseconds to sleep between retrying OLE clipboard operations.
+    /// </summary>
+    internal const int OleRetryDelay = 100;
+}
diff --git a/src/System.Private.Windows.Core/src/System/Private/Windows/Ole/ClipboardCore.cs b/src/System.Private.Windows.Core/src/System/Private/Windows/Ole/ClipboardCore.cs
index 994bbc07597..96018bcb342 100644
--- a/src/System.Private.Windows.Core/src/System/Private/Windows/Ole/ClipboardCore.cs
+++ b/src/System.Private.Windows.Core/src/System/Private/Windows/Ole/ClipboardCore.cs
@@ -12,23 +12,13 @@ namespace System.Private.Windows.Ole;
 internal static unsafe class ClipboardCore<TOleServices>
     where TOleServices : IOleServices
 {
-    /// <summary>
-    ///  The number of times to retry OLE clipboard operations.
-    /// </summary>
-    private const int OleRetryCount = 10;
-
-    /// <summary>
-    ///  The amount of time in milliseconds to sleep between retrying OLE clipboard operations.
-    /// </summary>
-    private const int OleRetryDelay = 100;
-
     /// <summary>
     ///  Removes all data from the Clipboard.
     /// </summary>
     /// <returns>An <see cref="HRESULT"/> indicating the success or failure of the operation.</returns>
     internal static HRESULT Clear(
-        int retryTimes = OleRetryCount,
-        int retryDelay = OleRetryDelay)
+        int retryTimes = ClipboardConstants.OleRetryCount,
+        int retryDelay = ClipboardConstants.OleRetryDelay)
     {
         TOleServices.EnsureThreadState();
 
@@ -53,8 +43,8 @@ internal static HRESULT Clear(
     /// </summary>
     /// <returns>An <see cref="HRESULT"/> indicating the success or failure of the operation.</returns>
     internal static HRESULT Flush(
-        int retryTimes = OleRetryCount,
-        int retryDelay = OleRetryDelay)
+        int retryTimes = ClipboardConstants.OleRetryCount,
+        int retryDelay = ClipboardConstants.OleRetryDelay)
     {
         TOleServices.EnsureThreadState();
 
@@ -85,8 +75,8 @@ internal static HRESULT Flush(
     internal static HRESULT SetData(
         IComVisibleDataObject dataObject,
         bool copy,
-        int retryTimes = OleRetryCount,
-        int retryDelay = OleRetryDelay)
+        int retryTimes = ClipboardConstants.OleRetryCount,
+        int retryDelay = ClipboardConstants.OleRetryDelay)
     {
         TOleServices.EnsureThreadState();
 
@@ -134,8 +124,8 @@ internal static HRESULT SetData(
     internal static HRESULT TryGetData(
         out ComScope<IDataObject> proxyDataObject,
         out object? originalObject,
-        int retryTimes = OleRetryCount,
-        int retryDelay = OleRetryDelay)
+        int retryTimes = ClipboardConstants.OleRetryCount,
+        int retryDelay = ClipboardConstants.OleRetryDelay)
     {
         TOleServices.EnsureThreadState();
 
@@ -184,8 +174,8 @@ internal static HRESULT TryGetData(
     /// <inheritdoc cref="SetData(IComVisibleDataObject, bool, int, int)"/>
     internal static bool IsObjectOnClipboard(
         object @object,
-        int retryTimes = OleRetryCount,
-        int retryDelay = OleRetryDelay)
+        int retryTimes = ClipboardConstants.OleRetryCount,
+        int retryDelay = ClipboardConstants.OleRetryDelay)
     {
         if (@object is null)
         {
@@ -210,8 +200,8 @@ internal static bool IsObjectOnClipboard(
     /// </summary>
     internal static HRESULT GetDataObject<TDataObject, TIDataObject>(
         out TIDataObject? dataObject,
-        int retryTimes = OleRetryCount,
-        int retryDelay = OleRetryDelay)
+        int retryTimes = ClipboardConstants.OleRetryCount,
+        int retryDelay = ClipboardConstants.OleRetryDelay)
         where TDataObject : class, IDataObjectInternal<TDataObject, TIDataObject>, TIDataObject
         where TIDataObject : class
     {
diff --git a/src/System.Private.Windows.Core/src/System/Private/Windows/Ole/Composition.NativeToManagedAdapter.cs b/src/System.Private.Windows.Core/src/System/Private/Windows/Ole/Composition.NativeToManagedAdapter.cs
index 115809900a6..4b1e6d3baba 100644
--- a/src/System.Private.Windows.Core/src/System/Private/Windows/Ole/Composition.NativeToManagedAdapter.cs
+++ b/src/System.Private.Windows.Core/src/System/Private/Windows/Ole/Composition.NativeToManagedAdapter.cs
@@ -359,12 +359,27 @@ private static bool TryGetHGLOBALData<T>(
                 tymed = (uint)Com.TYMED.TYMED_HGLOBAL
             };
 
-            if (dataObject->QueryGetData(formatetc).Failed)
+            HRESULT hr = HRESULT.S_OK;
+
+            Utilities.ExecuteWithRetry(() =>
+            {
+                hr = dataObject->QueryGetData(formatetc);
+                return hr == HRESULT.CLIPBRD_E_CANT_OPEN;
+            });
+
+            if (hr.Failed)
             {
                 return false;
             }
 
-            HRESULT hr = dataObject->GetData(formatetc, out Com.STGMEDIUM medium);
+            Com.STGMEDIUM medium = default;
+            hr = HRESULT.S_OK;
+
+            Utilities.ExecuteWithRetry(() =>
+            {
+                hr = dataObject->GetData(formatetc, out medium);
+                return hr == HRESULT.CLIPBRD_E_CANT_OPEN;
+            });
 
             // One of the ways this can happen is when we attempt to put binary formatted data onto the
             // clipboard, which will succeed as Windows ignores all errors when putting data on the clipboard.
@@ -376,6 +391,7 @@ private static bool TryGetHGLOBALData<T>(
             Debug.WriteLineIf(hr == HRESULT.E_UNEXPECTED, "E_UNEXPECTED returned when trying to get clipboard data.");
             Debug.WriteLineIf(hr == HRESULT.COR_E_SERIALIZATION,
                 "COR_E_SERIALIZATION returned when trying to get clipboard data, for example, BinaryFormatter threw SerializationException.");
+            Debug.WriteLineIf(hr == HRESULT.CLIPBRD_E_CANT_OPEN, "CLIPBRD_E_CANT_OPEN returned when clipboard was in locked state.");
 
             // If GetData failed, don't try to read from the medium - it may contain uninitialized data.
             // (This can easily happen when the clipboard content changes between QueryGetData and GetData calls.)
@@ -424,9 +440,30 @@ private static bool TryGetIStreamData<T>(
                 tymed = (uint)Com.TYMED.TYMED_ISTREAM
             };
 
+            HRESULT result = HRESULT.S_OK;
+
+            Utilities.ExecuteWithRetry(() =>
+            {
+                result = dataObject->QueryGetData(formatEtc);
+                return result == HRESULT.CLIPBRD_E_CANT_OPEN;
+            });
+
+            if (result.Failed)
+            {
+                return false;
+            }
+
+            Com.STGMEDIUM medium = default;
+            result = HRESULT.S_OK;
+
+            Utilities.ExecuteWithRetry(() =>
+            {
+                result = dataObject->GetData(formatEtc, out medium);
+                return result == HRESULT.CLIPBRD_E_CANT_OPEN;
+            });
+
             // Limit the # of exceptions we may throw below.
-            if (dataObject->QueryGetData(formatEtc).Failed
-                || dataObject->GetData(formatEtc, out Com.STGMEDIUM medium).Failed)
+            if (result.Failed)
             {
                 return false;
             }
diff --git a/src/System.Private.Windows.Core/src/System/Private/Windows/Ole/Utilities.cs b/src/System.Private.Windows.Core/src/System/Private/Windows/Ole/Utilities.cs
new file mode 100644
index 00000000000..b115e0df8df
--- /dev/null
+++ b/src/System.Private.Windows.Core/src/System/Private/Windows/Ole/Utilities.cs
@@ -0,0 +1,34 @@
+// Licensed to the .NET Foundation under one or more agreements.
+// The .NET Foundation licenses this file to you under the MIT license.
+
+namespace System.Private.Windows.Ole;
+
+internal static class Utilities
+{
+    /// <summary>
+    ///  Executes the given action with retry logic for OLE operations.
+    /// </summary>
+    /// <param name="action">Execute the action which returns bool value indicating whether to continue retries or stop.</param>
+    /// <param name="retryCount">Number of retry attempts.</param>
+    /// <param name="retryDelay">Delay in milliseconds between retries.</param>
+    internal static void ExecuteWithRetry(
+        Func<bool> action,
+        int retryCount = ClipboardConstants.OleRetryCount,
+        int retryDelay = ClipboardConstants.OleRetryDelay)
+    {
+        int attempts = 0;
+
+        while (attempts < retryCount)
+        {
+            if (action())
+            {
+                attempts++;
+                Thread.Sleep(retryDelay);
+
+                continue;
+            }
+
+            break;
+        }
+    }
+}
diff --git a/src/System.Private.Windows.Core/tests/System.Private.Windows.Core.Tests/System/Private/Windows/Ole/UtilitiesTests.cs b/src/System.Private.Windows.Core/tests/System.Private.Windows.Core.Tests/System/Private/Windows/Ole/UtilitiesTests.cs
new file mode 100644
index 00000000000..9fc225c3847
--- /dev/null
+++ b/src/System.Private.Windows.Core/tests/System.Private.Windows.Core.Tests/System/Private/Windows/Ole/UtilitiesTests.cs
@@ -0,0 +1,58 @@
+// Licensed to the .NET Foundation under one or more agreements.
+// The .NET Foundation licenses this file to you under the MIT license.
+
+namespace System.Private.Windows.Ole;
+
+public class UtilitiesTests
+{
+    [Fact]
+    public void ExecuteWithRetry_ActionReturnsFalse_CallsOnce()
+    {
+        int calls = 0;
+
+        Utilities.ExecuteWithRetry(() =>
+        {
+            calls++;
+
+            return false;
+        },
+        retryCount: 3,
+        retryDelay: 0);
+
+        Assert.Equal(1, calls);
+    }
+
+    [Fact]
+    public void ExecuteWithRetry_ActionReturnsTrueThenFalse_RetriesUntilFalse()
+    {
+        int calls = 0;
+
+        Utilities.ExecuteWithRetry(() =>
+        {
+            calls++;
+
+            return calls < 3;
+        },
+        retryCount: 5,
+        retryDelay: 0);
+
+        Assert.Equal(3, calls);
+    }
+
+    [Fact]
+    public void ExecuteWithRetry_ActionAlwaysReturnsTrue_StopsAtRetryCount()
+    {
+        int calls = 0;
+
+        Utilities.ExecuteWithRetry(() =>
+        {
+            calls++;
+
+            return true;
+        },
+        retryCount: 3,
+        retryDelay: 0);
+
+        Assert.Equal(3, calls);
+    }
+}
diff --git a/src/System.Windows.Forms/System/Windows/Forms/OLE/WinFormsOleServices.cs b/src/System.Windows.Forms/System/Windows/Forms/OLE/WinFormsOleServices.cs
index 7bf810195bd..3e091d9558a 100644
--- a/src/System.Windows.Forms/System/Windows/Forms/OLE/WinFormsOleServices.cs
+++ b/src/System.Windows.Forms/System/Windows/Forms/OLE/WinFormsOleServices.cs
@@ -85,19 +85,34 @@ static unsafe bool TryGetBitmapData(Com.IDataObject* dataObject, [NotNullWhen(tr
                 tymed = (uint)TYMED.TYMED_GDI
             };
 
-            HRESULT result = dataObject->QueryGetData(formatEtc);
+            HRESULT result = HRESULT.S_OK;
+
+            Utilities.ExecuteWithRetry(() =>
+            {
+                result = dataObject->QueryGetData(formatEtc);
+                return result == HRESULT.CLIPBRD_E_CANT_OPEN;
+            });
+
             if (result.Failed)
             {
                 return false;
             }
 
-            result = dataObject->GetData(formatEtc, out STGMEDIUM medium);
+            result = HRESULT.S_OK;
+            STGMEDIUM medium = default;
+
+            Utilities.ExecuteWithRetry(() =>
+            {
+                result = dataObject->GetData(formatEtc, out medium);
+                return result == HRESULT.CLIPBRD_E_CANT_OPEN;
+            });
 
             // One of the ways this can happen is when we attempt to put binary formatted data onto the
             // clipboard, which will succeed as Windows ignores all errors when putting data on the clipboard.
             // The data state, however, is not good, and this error will be returned by Windows when asking to
             // get the data out.
             Debug.WriteLineIf(result == HRESULT.CLIPBRD_E_BAD_DATA, "CLIPBRD_E_BAD_DATA returned when trying to get clipboard data.");
+            Debug.WriteLineIf(result == HRESULT.CLIPBRD_E_CANT_OPEN, "CLIPBRD_E_CANT_OPEN returned when clipboard was in locked state.");
 
             try
             {