diff --git a/winforms/src/toga_winforms/app.py b/winforms/src/toga_winforms/app.py
index 8c98fefa36..0bdddd9f5a 100644
--- a/winforms/src/toga_winforms/app.py
+++ b/winforms/src/toga_winforms/app.py
@@ -364,6 +364,8 @@ def hide_cursor(self):
     def winforms_DisplaySettingsChanged(self, sender, event):
         for window in self.interface.windows:
             window._impl.update_scale()
+            if window._impl.toolbar_native is not None:
+                window._impl.update_toolbar_font_scale()
             if isinstance(window._impl, MainWindow):
                 window._impl.update_menubar_font_scale()
             for widget in window.widgets:
diff --git a/winforms/src/toga_winforms/window.py b/winforms/src/toga_winforms/window.py
index 2fda2d151e..4d9f7422c4 100644
--- a/winforms/src/toga_winforms/window.py
+++ b/winforms/src/toga_winforms/window.py
@@ -1,5 +1,5 @@
 import System.Windows.Forms as WinForms
-from System.Drawing import Bitmap, Graphics, Point, Size
+from System.Drawing import Bitmap, Font as WinFont, Graphics, Point, Size
 from System.Drawing.Imaging import ImageFormat
 from System.IO import MemoryStream
 
@@ -72,13 +72,21 @@ def create_toolbar(self):
                     item.Click += WeakrefCallable(cmd._impl.winforms_handler)
                     cmd._impl.native.append(item)
                 self.toolbar_native.Items.Add(item)
-
+            self.original_toolbar_font = self.toolbar_native.Font
         elif self.toolbar_native:
             self.native.Controls.Remove(self.toolbar_native)
             self.toolbar_native = None
 
         self.resize_content()
 
+    def update_toolbar_font_scale(self):
+        if self.toolbar_native is not None:
+            self.toolbar_native.Font = WinFont(
+                self.original_toolbar_font.FontFamily,
+                self.scale_font(self.original_toolbar_font.Size),
+                self.original_toolbar_font.Style,
+            )
+
     def get_position(self):
         location = self.native.Location
         return tuple(map(self.scale_out, (location.X, location.Y)))