diff --git a/src/System.Windows.Forms/System/Windows/Forms/Controls/Buttons/CheckBox.cs b/src/System.Windows.Forms/System/Windows/Forms/Controls/Buttons/CheckBox.cs
index da9e1353c2b..57526b2644b 100644
--- a/src/System.Windows.Forms/System/Windows/Forms/Controls/Buttons/CheckBox.cs
+++ b/src/System.Windows.Forms/System/Windows/Forms/Controls/Buttons/CheckBox.cs
@@ -75,6 +75,13 @@ public Appearance Appearance
             using (LayoutTransaction.CreateTransactionIf(AutoSize, ParentInternal, this, PropertyNames.Appearance))
             {
                 _appearance = value;
+
+                // UpdateOwnerDraw synchronizes control styles with the OwnerDraw state and recreates
+                // the handle if they differ. Since we hijack FlatStyle.Standard for DarkMode, the transition
+                // between Normal and Button appearance is critical for updating the OwnerDraw flag.
+                UpdateOwnerDraw();
+
+                // If handle wasn't recreated (OwnerDraw state didn't change), refresh the appearance.
                 if (OwnerDraw)
                 {
                     Refresh();
@@ -82,11 +89,6 @@ public Appearance Appearance
                 else
                 {
                     UpdateStyles();
-
-                    // UpdateStyles should also update the UserDraw flag, but it doesn't.
-                    // Since we hijack FlatStyle.Standard for DarkMode and let that SystemRender,
-                    // the threshold from Normal to Button is important to update the OwnerDraw flag.
-                    UpdateOwnerDraw();
                 }
 
                 OnAppearanceChanged(EventArgs.Empty);
diff --git a/src/System.Windows.Forms/System/Windows/Forms/Controls/Buttons/RadioButton.cs b/src/System.Windows.Forms/System/Windows/Forms/Controls/Buttons/RadioButton.cs
index 1b04ac32b52..a6674f1ea69 100644
--- a/src/System.Windows.Forms/System/Windows/Forms/Controls/Buttons/RadioButton.cs
+++ b/src/System.Windows.Forms/System/Windows/Forms/Controls/Buttons/RadioButton.cs
@@ -89,6 +89,11 @@ public Appearance Appearance
                 using (LayoutTransaction.CreateTransactionIf(AutoSize, ParentInternal, this, PropertyNames.Appearance))
                 {
                     _appearance = value;
+
+                    // UpdateOwnerDraw checks if OwnerDraw state changed and calls RecreateHandle if needed.
+                    UpdateOwnerDraw();
+
+                    // If handle wasn't recreated (OwnerDraw state didn't change), refresh the appearance.
                     if (OwnerDraw)
                     {
                         Refresh();
@@ -96,9 +101,6 @@ public Appearance Appearance
                     else
                     {
                         UpdateStyles();
-
-                        // UpdateStyles should also update the UserDraw flag, but it doesn't.
-                        UpdateOwnerDraw();
                     }
 
                     OnAppearanceChanged(EventArgs.Empty);