diff --git a/src/System.Windows.Forms/src/System/Windows/Forms/LinkLabel.cs b/src/System.Windows.Forms/src/System/Windows/Forms/LinkLabel.cs
index 123873bc7fe..c83cced2d6a 100644
--- a/src/System.Windows.Forms/src/System/Windows/Forms/LinkLabel.cs
+++ b/src/System.Windows.Forms/src/System/Windows/Forms/LinkLabel.cs
@@ -1506,7 +1506,12 @@ protected override void OnTextAlignChanged(EventArgs e)
                             font,
                             clientRectWithPadding,
                             brushColor,
-                            CreateTextFormatFlags(clientRectWithPadding.Size));
+                            CreateTextFormatFlags(clientRectWithPadding.Size)
+#if DEBUG
+                            // Skip the asserts in TextRenderer because the DC has been modified
+                            | TextRenderer.SkipAssertFlag
+#endif
+                            );
                     }
 
                     if (Focused && ShowFocusCues && FocusLink == link)
diff --git a/src/System.Windows.Forms/src/System/Windows/Forms/TextFormatFlags.cs b/src/System.Windows.Forms/src/System/Windows/Forms/TextFormatFlags.cs
index eca377acecf..2bbed8686ec 100644
--- a/src/System.Windows.Forms/src/System/Windows/Forms/TextFormatFlags.cs
+++ b/src/System.Windows.Forms/src/System/Windows/Forms/TextFormatFlags.cs
@@ -15,59 +15,58 @@ namespace System.Windows.Forms
     [Flags]
     public enum TextFormatFlags
     {
-        Bottom = (int)User32.DT.BOTTOM,
-        EndEllipsis = (int)User32.DT.END_ELLIPSIS,
-        ExpandTabs = (int)User32.DT.EXPANDTABS,
-        ExternalLeading = (int)User32.DT.EXTERNALLEADING,
-        Default = (int)User32.DT.DEFAULT,
-        HidePrefix = (int)User32.DT.HIDEPREFIX,
-        HorizontalCenter = (int)User32.DT.CENTER,
-        Internal = (int)User32.DT.INTERNAL,
+        Bottom                              = (int)User32.DT.BOTTOM,
+        EndEllipsis                         = (int)User32.DT.END_ELLIPSIS,
+        ExpandTabs                          = (int)User32.DT.EXPANDTABS,
+        ExternalLeading                     = (int)User32.DT.EXTERNALLEADING,
+        Default                             = (int)User32.DT.DEFAULT,
+        HidePrefix                          = (int)User32.DT.HIDEPREFIX,
+        HorizontalCenter                    = (int)User32.DT.CENTER,
+        Internal                            = (int)User32.DT.INTERNAL,
 
         /// <remarks>
         ///  This is the default.
         /// </remarks>
-        Left = (int)User32.DT.LEFT,
+        Left                                = (int)User32.DT.LEFT,
 
         [Obsolete("ModifyString mutates strings and should be avoided. It will be blocked in a future release.")]
-        ModifyString = (int)User32.DT.MODIFYSTRING,
-        NoClipping = (int)User32.DT.NOCLIP,
-        NoPrefix = (int)User32.DT.NOPREFIX,
-        NoFullWidthCharacterBreak = (int)User32.DT.NOFULLWIDTHCHARBREAK,
-        PathEllipsis = (int)User32.DT.PATH_ELLIPSIS,
-        PrefixOnly = (int)User32.DT.PREFIXONLY,
-        Right = (int)User32.DT.RIGHT,
-        RightToLeft = (int)User32.DT.RTLREADING,
-        SingleLine = (int)User32.DT.SINGLELINE,
-        TextBoxControl = (int)User32.DT.EDITCONTROL,
+        ModifyString                        = (int)User32.DT.MODIFYSTRING,
+        NoClipping                          = (int)User32.DT.NOCLIP,
+        NoPrefix                            = (int)User32.DT.NOPREFIX,
+        NoFullWidthCharacterBreak           = (int)User32.DT.NOFULLWIDTHCHARBREAK,
+        PathEllipsis                        = (int)User32.DT.PATH_ELLIPSIS,
+        PrefixOnly                          = (int)User32.DT.PREFIXONLY,
+        Right                               = (int)User32.DT.RIGHT,
+        RightToLeft                         = (int)User32.DT.RTLREADING,
+        SingleLine                          = (int)User32.DT.SINGLELINE,
+        TextBoxControl                      = (int)User32.DT.EDITCONTROL,
 
         /// <remarks>
         ///  This is the default.
         /// </remarks>
-        Top = (int)User32.DT.TOP,
+        Top                                 = (int)User32.DT.TOP,
 
-        VerticalCenter = (int)User32.DT.VCENTER,
-        WordBreak = (int)User32.DT.WORDBREAK,
-        WordEllipsis = (int)User32.DT.WORD_ELLIPSIS,
+        VerticalCenter                      = (int)User32.DT.VCENTER,
+        WordBreak                           = (int)User32.DT.WORDBREAK,
+        WordEllipsis                        = (int)User32.DT.WORD_ELLIPSIS,
 
-        /// <summary>
         ///  The following flags are exclusive of TextRenderer (no Windows native flags)
         ///  and apply to methods receiving a Graphics as the IDeviceContext object, and
         ///  specify whether to reapply clipping and coordintate transformations to the hdc
         ///  obtained from the Graphics object, which returns a clean hdc.
-        /// </summary>
-        PreserveGraphicsClipping = 0x01000000,
-        PreserveGraphicsTranslateTransform = 0x02000000,
+        ///
+        ///  These get stripped off by TextExtensions before we call DrawText or MeasureText
+        ///  (see: GdiUnsupportedFlagMask).
+
+        PreserveGraphicsClipping            = 0x0100_0000,
+        PreserveGraphicsTranslateTransform  = 0x0200_0000,
 
         /// <summary>
         ///  Adds padding related to the drawing binding box, computed according to the font size.
         ///  Match the System.Internal.GDI.TextPaddingOptions.
         /// </summary>
-        /// <remarks>
-        ///  This is the default.
-        /// </remarks>
-        GlyphOverhangPadding = 0x00000000,
-        NoPadding = 0x10000000,
-        LeftAndRightPadding = 0x20000000
+        GlyphOverhangPadding                = 0x0000_0000,
+        NoPadding                           = 0x1000_0000,
+        LeftAndRightPadding                 = 0x2000_0000
     }
 }
diff --git a/src/System.Windows.Forms/src/System/Windows/Forms/TextRenderer.cs b/src/System.Windows.Forms/src/System/Windows/Forms/TextRenderer.cs
index 05272586f8a..377f4e8206c 100644
--- a/src/System.Windows.Forms/src/System/Windows/Forms/TextRenderer.cs
+++ b/src/System.Windows.Forms/src/System/Windows/Forms/TextRenderer.cs
@@ -14,6 +14,13 @@ namespace System.Windows.Forms
     /// </summary>
     public static class TextRenderer
     {
+#if DEBUG
+        // In various cases the DC may have already been modified, and we don't pass TextFormatFlags.PreserveGraphicsClipping
+        // or TextFormatFlags.PreserveGraphicsTranslateTransform flags, that set off the asserts in GetApplyStateFlags
+        // method. This flags allows us to skip those assert for the cases we know we don't need these flags.
+        internal static TextFormatFlags SkipAssertFlag = (TextFormatFlags)0x4000_0000;
+#endif
+
         internal static Gdi32.QUALITY DefaultQuality { get; } = GetDefaultFontQuality();
 
         internal static Size MaxSize { get; } = new Size(int.MaxValue, int.MaxValue);
@@ -620,15 +627,20 @@ private static ApplyGraphicsProperties GetApplyStateFlags(IDeviceContext deviceC
                 apply |= ApplyGraphicsProperties.TranslateTransform;
             }
 
-            Debug.Assert(apply.HasFlag(ApplyGraphicsProperties.Clipping)
-                || graphics.Clip is null
-                || graphics.Clip.GetHrgn(graphics) == IntPtr.Zero,
-                "Must preserve Graphics clipping region!");
-
-            Debug.Assert(apply.HasFlag(ApplyGraphicsProperties.TranslateTransform)
-                || graphics.Transform is null
-                || graphics.Transform.IsIdentity,
-                "Must preserve Graphics transformation!");
+#if DEBUG
+            if ((textFormatFlags & SkipAssertFlag) == 0)
+            {
+                Debug.Assert(apply.HasFlag(ApplyGraphicsProperties.Clipping)
+                    || graphics.Clip is null
+                    || graphics.Clip.GetHrgn(graphics) == IntPtr.Zero,
+                    "Must preserve Graphics clipping region!");
+
+                Debug.Assert(apply.HasFlag(ApplyGraphicsProperties.TranslateTransform)
+                    || graphics.Transform is null
+                    || graphics.Transform.IsIdentity,
+                    "Must preserve Graphics transformation!");
+            }
+#endif
 
             return apply;
         }