diff --git a/src/System.Windows.Forms/System/Windows/Forms/Controls/TreeView/TreeView.cs b/src/System.Windows.Forms/System/Windows/Forms/Controls/TreeView/TreeView.cs
index 4d6a3c53602..91c61491aee 100644
--- a/src/System.Windows.Forms/System/Windows/Forms/Controls/TreeView/TreeView.cs
+++ b/src/System.Windows.Forms/System/Windows/Forms/Controls/TreeView/TreeView.cs
@@ -2782,12 +2782,16 @@ private unsafe void CustomDraw(ref Message m)
                 if (renderinfo is not null && renderinfo.Font is not null)
                 {
                     // Mess with the DC directly...
-                    PInvokeCore.SelectObject(nmtvcd->nmcd.hdc, renderinfo.FontHandle);
+                    Debug.Assert(node._propBag is not null);
+                    if (node._propBag is not null && node._propBag.Font is not null)
+                    {
+                        PInvokeCore.SelectObject(nmtvcd->nmcd.hdc, node._propBag.FontHandle);
 
-                    // There is a problem in winctl that clips node fonts if the fontSize
-                    // is larger than the treeView font size. The behavior is much better in comctl 5 and above.
-                    m.ResultInternal = (LRESULT)(nint)PInvoke.CDRF_NEWFONT;
-                    return;
+                        // There is a problem in winctl that clips node fonts if the fontSize
+                        // is larger than the treeView font size. The behavior is much better in comctl 5 and above.
+                        m.ResultInternal = (LRESULT)(nint)PInvoke.CDRF_NEWFONT;
+                        return;
+                    }
                 }
 
                 // fall through and do the default drawing work
diff --git a/src/System.Windows.Forms/System/Windows/Forms/OwnerDrawPropertyBag.cs b/src/System.Windows.Forms/System/Windows/Forms/OwnerDrawPropertyBag.cs
index a5e39cb6475..c78c4232e50 100644
--- a/src/System.Windows.Forms/System/Windows/Forms/OwnerDrawPropertyBag.cs
+++ b/src/System.Windows.Forms/System/Windows/Forms/OwnerDrawPropertyBag.cs
@@ -12,6 +12,7 @@ namespace System.Windows.Forms;
 [Serializable] // This class is participating in resx serialization scenarios for listview/treeview items.
 public class OwnerDrawPropertyBag : MarshalByRefObject, ISerializable
 {
+    private Font? _font;
     private Control.FontHandleWrapper? _fontWrapper;
     private static readonly Lock s_internalSyncObject = new();
 
@@ -38,7 +39,19 @@ internal OwnerDrawPropertyBag()
     {
     }
 
-    public Font? Font { get; set; }
+    public Font? Font
+    {
+        get => _font;
+        set
+        {
+            if (!ReferenceEquals(_font, value))
+            {
+                _font = value;
+                _fontWrapper?.Dispose();
+                _fontWrapper = null;
+            }
+        }
+    }
 
     public Color ForeColor { get; set; }
 
diff --git a/src/test/unit/System.Windows.Forms/System/Windows/Forms/OwnerDrawPropertyBagTests.cs b/src/test/unit/System.Windows.Forms/System/Windows/Forms/OwnerDrawPropertyBagTests.cs
index b95c33e3378..650d207037c 100644
--- a/src/test/unit/System.Windows.Forms/System/Windows/Forms/OwnerDrawPropertyBagTests.cs
+++ b/src/test/unit/System.Windows.Forms/System/Windows/Forms/OwnerDrawPropertyBagTests.cs
@@ -4,6 +4,7 @@
 #nullable disable
 
 using System.Drawing;
+using System.Reflection;
 using System.Runtime.Serialization.Formatters.Binary;
 using System.Windows.Forms.TestUtilities;
 
@@ -56,6 +57,24 @@ public void OwnerDrawPropertyBag_Font_Set_GetReturnsExpected(Font value)
         Assert.Equal(value is null, bag.IsEmpty());
     }
 
+    [WinFormsFact]
+    public void OwnerDrawPropertyBag_Font_SetDifferentValue_ResetsCachedFontWrapper()
+    {
+        using SubTreeView treeView = new();
+        OwnerDrawPropertyBag bag = treeView.GetItemRenderStyles(null, 0);
+        using Font firstFont = new(SystemFonts.MenuFont, FontStyle.Regular);
+        using Font secondFont = new(SystemFonts.MenuFont, FontStyle.Bold);
+
+        bag.Font = firstFont;
+        _ = bag.GetType().GetProperty("FontHandle", BindingFlags.Instance | BindingFlags.NonPublic)!.GetValue(bag);
+
+        FieldInfo fontWrapperField = bag.GetType().GetField("_fontWrapper", BindingFlags.Instance | BindingFlags.NonPublic)!;
+        Assert.NotNull(fontWrapperField.GetValue(bag));
+
+        bag.Font = secondFont;
+        Assert.Null(fontWrapperField.GetValue(bag));
+    }
+
     [WinFormsTheory]
     [CommonMemberData(typeof(CommonTestHelper), nameof(CommonTestHelper.GetColorWithEmptyTheoryData))]
     public void OwnerDrawPropertyBag_ForeColor_Set_GetReturnsExpected(Color value)