diff --git a/src/System.Windows.Forms/System/Windows/Forms/Controls/ToolStrips/ToolStripRenderer.cs b/src/System.Windows.Forms/System/Windows/Forms/Controls/ToolStrips/ToolStripRenderer.cs
index 5ce502caaaf..b62c48db870 100644
--- a/src/System.Windows.Forms/System/Windows/Forms/Controls/ToolStrips/ToolStripRenderer.cs
+++ b/src/System.Windows.Forms/System/Windows/Forms/Controls/ToolStrips/ToolStripRenderer.cs
@@ -856,27 +856,50 @@ protected virtual void OnRenderItemCheck(ToolStripItemImageRenderEventArgs e)
             return;
         }
 
+        // Track images we allocate so they can be disposed after drawing.
+        Image? disabledImage = null;
+        Image? invertedImage = null;
+
         if (e.Item is not null)
         {
             if (!e.Item.Enabled)
             {
-                image = CreateDisabledImage(image, e.ImageAttributes);
+                disabledImage = CreateDisabledImage(image, e.ImageAttributes);
+                image = disabledImage;
             }
 
-            if (SystemInformation.HighContrast && image is Bitmap bitmap)
+            if (image is Bitmap bitmap)
             {
-                Color backgroundColor = e.Item.Selected ? SystemColors.Highlight : e.Item.BackColor;
+                if (SystemInformation.HighContrast)
+                {
+                    Color backgroundColor = e.Item.Selected ? SystemColors.Highlight : e.Item.BackColor;
 
-                if (ControlPaint.IsDark(backgroundColor))
+                    if (ControlPaint.IsDark(backgroundColor))
+                    {
+                        invertedImage = ControlPaint.CreateBitmapWithInvertedForeColor(bitmap, backgroundColor);
+                        image = invertedImage;
+                    }
+                }
+                else if (Application.IsDarkModeEnabled)
                 {
-                    Image invertedImage = ControlPaint.CreateBitmapWithInvertedForeColor(bitmap, e.Item.BackColor);
-                    image = invertedImage;
+                    Color backgroundColor = e.Item.Selected ? SystemColors.Highlight : e.Item.BackColor;
+
+                    if (ControlPaint.IsDark(backgroundColor))
+                    {
+                        // In dark mode, the check mark icons are dark glyphs designed for light
+                        // backgrounds. Invert the foreground color so they are visible on dark backgrounds.
+                        invertedImage = ControlPaint.CreateBitmapWithInvertedForeColor(bitmap, backgroundColor);
+                        image = invertedImage;
+                    }
                 }
             }
         }
 
         e.Graphics.DrawImage(image, imageRect, 0, 0, imageRect.Width,
         imageRect.Height, GraphicsUnit.Pixel, e.ImageAttributes);
+
+        disabledImage?.Dispose();
+        invertedImage?.Dispose();
     }
 
     /// <summary>