diff --git a/android/tests_backend/widgets/base.py b/android/tests_backend/widgets/base.py
index fae94f78b7..ac82ef521b 100644
--- a/android/tests_backend/widgets/base.py
+++ b/android/tests_backend/widgets/base.py
@@ -16,9 +16,15 @@ def assert_container(self, container):
         else:
             raise AssertionError(f"cannot find {self.native} in {container_native}")
 
+    def alignment_equivalent(self, actual, expected):
+        assert actual == expected
+        return True
+
     async def redraw(self):
         """Request a redraw of the app, waiting until that redraw has completed."""
-        # Refresh the layout
+        # TODO: Travertino/Pack doesn't force a layout refresh
+        # when properties such as flex or width are altered.
+        # For now, do a manual refresh.
         self.widget.window.content.refresh()
 
     @property
diff --git a/cocoa/src/toga_cocoa/constraints.py b/cocoa/src/toga_cocoa/constraints.py
index 8cfa10beb0..dcf5b2ac0f 100644
--- a/cocoa/src/toga_cocoa/constraints.py
+++ b/cocoa/src/toga_cocoa/constraints.py
@@ -31,6 +31,7 @@ def container(self):
     @container.setter
     def container(self, value):
         if value is None and self.container:
+            # print("Remove constraints for", self.widget, 'in', self.container)
             self.container.native.removeConstraint(self.width_constraint)
             self.container.native.removeConstraint(self.height_constraint)
             self.container.native.removeConstraint(self.left_constraint)
@@ -84,9 +85,8 @@ def container(self, value):
             self.container.native.addConstraint(self.height_constraint)
 
     def update(self, x, y, width, height):
-        # print("UPDATE", self.widget, 'in', self.container, 'to', x, y, width, height)
         if self.container:
-            # print("IN CONTAINER")
+            # print("UPDATE", self.widget, 'in', self.container, 'to', x, y, width, height)
             self.left_constraint.constant = x
             self.top_constraint.constant = y
 
diff --git a/cocoa/tests_backend/widgets/base.py b/cocoa/tests_backend/widgets/base.py
index b4efbbfabb..572a2804b4 100644
--- a/cocoa/tests_backend/widgets/base.py
+++ b/cocoa/tests_backend/widgets/base.py
@@ -12,10 +12,17 @@ def assert_container(self, container):
         else:
             raise ValueError(f"cannot find {self.native} in {container_native}")
 
+    def alignment_equivalent(self, actual, expected):
+        assert actual == expected
+        return True
+
     async def redraw(self):
         """Request a redraw of the app, waiting until that redraw has completed."""
-        # Refresh the layout
+        # TODO: Travertino/Pack doesn't force a layout refresh
+        # when properties such as flex or width are altered.
+        # For now, do a manual refresh.
         self.widget.window.content.refresh()
+
         # Force a repaint
         self.widget.window.content._impl.native.displayIfNeeded()
 
diff --git a/cocoa/tests_backend/widgets/properties.py b/cocoa/tests_backend/widgets/properties.py
index a6a4206cc1..99b701ec0c 100644
--- a/cocoa/tests_backend/widgets/properties.py
+++ b/cocoa/tests_backend/widgets/properties.py
@@ -1,4 +1,4 @@
-from dataclasses import dataclass
+from travertino.fonts import Font
 
 from toga.colors import rgba
 from toga.fonts import FANTASY, NORMAL, SYSTEM
@@ -23,15 +23,6 @@ def toga_color(color):
         return None
 
 
-@dataclass
-class Font:
-    family: str
-    size: int
-    style: str = NORMAL
-    variant: str = NORMAL
-    weight: str = NORMAL
-
-
 def toga_font(font):
     return Font(
         family={
@@ -39,6 +30,9 @@ def toga_font(font):
             "Papyrus": FANTASY,
         }.get(str(font.familyName), str(font.familyName)),
         size=font.pointSize,
+        style=NORMAL,  # TODO: ITALIC if..., SMALL_CAPS if ...
+        variant=NORMAL,
+        weight=NORMAL,  # TODO: BOLD if ...
     )
 
 
diff --git a/core/src/toga/style/applicator.py b/core/src/toga/style/applicator.py
index f45418d648..e2b820f2ad 100644
--- a/core/src/toga/style/applicator.py
+++ b/core/src/toga/style/applicator.py
@@ -9,7 +9,7 @@ def refresh(self):
         self.widget.refresh()
 
     def set_bounds(self):
-        # print("APPLY LAYOUT", self.widget, self.widget.layout)
+        # print("  APPLY LAYOUT", self.widget, self.widget.layout)
         self.widget._impl.set_bounds(
             self.widget.layout.absolute_content_left,
             self.widget.layout.absolute_content_top,
@@ -27,8 +27,11 @@ def set_hidden(self, hidden):
         self.widget._impl.set_hidden(hidden)
 
     def set_font(self, font):
+        # Changing the font of a widget can make the widget change size,
+        # which in turn means we need to do a re-layout
         self.widget._impl.set_font(font)
         self.widget._impl.rehint()
+        self.widget.refresh()
 
     def set_color(self, color):
         self.widget._impl.set_color(color)
diff --git a/core/src/toga/widgets/button.py b/core/src/toga/widgets/button.py
index 026aebd04a..97a0b7b3d1 100644
--- a/core/src/toga/widgets/button.py
+++ b/core/src/toga/widgets/button.py
@@ -47,7 +47,10 @@ def text(self, value):
         else:
             value = str(value)
         self._impl.set_text(value)
+        # Changing the text will probably cause the size of the button to change
+        # so we need to rehint, then recompute layout.
         self._impl.rehint()
+        self.refresh()
 
     @property
     def on_press(self):
diff --git a/core/src/toga/widgets/label.py b/core/src/toga/widgets/label.py
index 1c9603380e..22ad648fd9 100644
--- a/core/src/toga/widgets/label.py
+++ b/core/src/toga/widgets/label.py
@@ -50,4 +50,7 @@ def text(self, value):
         else:
             self._text = str(value)
         self._impl.set_text(value)
+        # Changing the text will probably cause the size of the label to change
+        # so we need to rehint, then recompute layout.
         self._impl.rehint()
+        self.refresh()
diff --git a/core/src/toga/widgets/switch.py b/core/src/toga/widgets/switch.py
index 85fd8aea75..3875575bb4 100644
--- a/core/src/toga/widgets/switch.py
+++ b/core/src/toga/widgets/switch.py
@@ -140,7 +140,10 @@ def text(self, value):
         else:
             self._text = str(value)
         self._impl.set_text(value)
+        # Changing the text will probably cause the size of the switch to change
+        # so we need to rehint, then recompute layout.
         self._impl.rehint()
+        self.refresh()
 
     @property
     def on_change(self):
diff --git a/docs/reference/api/widgets/label.rst b/docs/reference/api/widgets/label.rst
index cf684b94c1..5ee8be3440 100644
--- a/docs/reference/api/widgets/label.rst
+++ b/docs/reference/api/widgets/label.rst
@@ -22,6 +22,12 @@ Usage
 
     label = toga.Label('Hello world')
 
+Notes
+-----
+
+* Winforms does not support an alignment value of ``JUSTIFIED``. If this
+  alignment value is used, the label will default left alignment.
+
 Reference
 ---------
 
diff --git a/gtk/tests_backend/widgets/base.py b/gtk/tests_backend/widgets/base.py
index 8554bd76e3..f975e6a86a 100644
--- a/gtk/tests_backend/widgets/base.py
+++ b/gtk/tests_backend/widgets/base.py
@@ -18,6 +18,10 @@ def assert_container(self, container):
         else:
             raise ValueError(f"cannot find {self.native} in {container_native}")
 
+    def alignment_equivalent(self, actual, expected):
+        assert actual == expected
+        return True
+
     async def redraw(self):
         """Request a redraw of the app, waiting until that redraw has completed."""
         # Force a repaint
diff --git a/iOS/tests_backend/widgets/base.py b/iOS/tests_backend/widgets/base.py
index 4de90e3dd3..a903079157 100644
--- a/iOS/tests_backend/widgets/base.py
+++ b/iOS/tests_backend/widgets/base.py
@@ -40,12 +40,18 @@ def assert_container(self, container):
         else:
             raise ValueError(f"cannot find {self.native} in {container_native}")
 
+    def alignment_equivalent(self, actual, expected):
+        assert actual == expected
+        return True
+
     async def redraw(self):
         """Request a redraw of the app, waiting until that redraw has completed."""
-        # Refresh the layout
+        # TODO: Travertino/Pack doesn't force a layout refresh
+        # when properties such as flex or width are altered.
+        # For now, do a manual refresh.
         self.widget.window.content.refresh()
+
         # Force a repaint
-        #        self.widget.window.content._impl.native.layer.setNeedsDisplay_(True)
         self.widget.window.content._impl.native.layer.displayIfNeeded()
 
     @property
diff --git a/testbed/tests/widgets/properties.py b/testbed/tests/widgets/properties.py
index 640b060fe2..e2ca5e8556 100644
--- a/testbed/tests/widgets/properties.py
+++ b/testbed/tests/widgets/properties.py
@@ -73,7 +73,7 @@ async def test_color(widget, probe):
 
 
 @mark.skipif(
-    current_platform in {"android", "windows"},
+    current_platform in {"android"},
     reason="color resets don't work",
 )
 async def test_color_reset(widget, probe):
@@ -111,10 +111,7 @@ async def test_background_color_reset(widget, probe):
     assert_color(probe.background_color, original)
 
 
-@mark.skipif(
-    current_platform == "windows",
-    reason="TRANSPARENT not implemented",
-)
 async def test_background_color_transparent(widget, probe):
+    "Background transparency is treated as a color reset"
     widget.style.background_color = TRANSPARENT
     assert_color(probe.background_color, TRANSPARENT)
diff --git a/testbed/tests/widgets/test_button.py b/testbed/tests/widgets/test_button.py
index 3cb46fac46..3bf9555c5a 100644
--- a/testbed/tests/widgets/test_button.py
+++ b/testbed/tests/widgets/test_button.py
@@ -18,6 +18,12 @@
     test_text_width_change,
 )
 
+
+@fixture
+async def widget():
+    return toga.Button("Hello")
+
+
 test_font = mark.skipif(
     current_platform in {"iOS"},
     reason="font changes don't alter size",
@@ -28,12 +34,6 @@
     reason="round trip empty strings don't work",
 )(test_text)
 
-
-@fixture
-async def widget():
-    return toga.Button("Hello")
-
-
 test_text_width_change = mark.skipif(
     current_platform in {"linux"},
     reason="resizes not applying correctly",
@@ -54,10 +54,6 @@ async def test_press(widget, probe):
     handler.assert_called_once_with(widget)
 
 
-@mark.skipif(
-    current_platform in {"windows"},
-    reason="color reset on transparent not implemented",
-)
 async def test_background_color_transparent(widget, probe):
     "Buttons treat background transparency as a color reset."
     widget.style.background_color = TRANSPARENT
@@ -75,10 +71,10 @@ async def test_background_color_transparent(widget, probe):
 async def test_button_size(widget, probe):
     "Check that the button resizes"
     # Container is initially a non-flex row box.
-    # Initial button size is small, based on content size.
+    # Initial button size is small (but non-zero), based on content size.
     await probe.redraw()
-    assert 50 <= probe.width <= 100
-    assert probe.height <= 50
+    assert 10 <= probe.width <= 100
+    assert 10 <= probe.height <= 50
 
     # Make the button flexible; it will expand to fill horizontal space
     widget.style.flex = 1
diff --git a/testbed/tests/widgets/test_label.py b/testbed/tests/widgets/test_label.py
index c034af1320..2893132b5a 100644
--- a/testbed/tests/widgets/test_label.py
+++ b/testbed/tests/widgets/test_label.py
@@ -51,14 +51,14 @@ def make_lines(n):
 
 
 async def test_alignment(widget, probe):
-    # Initial alignment is LEFT
+    # Initial alignment is LEFT, initial direction is LTR
     widget.parent.style.direction = COLUMN
     assert probe.alignment == LEFT
 
     for alignment in [RIGHT, CENTER, JUSTIFY]:
         widget.style.text_align = alignment
         await probe.redraw()
-        assert probe.alignment == alignment
+        assert probe.alignment_equivalent(probe.alignment, alignment)
 
     # Clearing the alignment reverts to default alignment of LEFT
     widget.style.text_align = None
diff --git a/winforms/src/toga_winforms/libs/__init__.py b/winforms/src/toga_winforms/libs/__init__.py
index b0d3166c37..029ef9b4f4 100644
--- a/winforms/src/toga_winforms/libs/__init__.py
+++ b/winforms/src/toga_winforms/libs/__init__.py
@@ -8,6 +8,7 @@
     Action,
     Bitmap,
     Color,
+    ContentAlignment,
     Convert,
     CultureInfo,
     Drawing2D,
@@ -32,6 +33,7 @@
     String,
     StringFormat,
     SystemColors,
+    SystemFonts,
     Task,
     TaskScheduler,
     Threading,
diff --git a/winforms/src/toga_winforms/widgets/base.py b/winforms/src/toga_winforms/widgets/base.py
index 3f9eb3454d..92466b9b0b 100644
--- a/winforms/src/toga_winforms/widgets/base.py
+++ b/winforms/src/toga_winforms/widgets/base.py
@@ -1,4 +1,5 @@
-from toga_winforms.libs import Point, Size
+from toga_winforms.colors import native_color
+from toga_winforms.libs import Point, Size, SystemColors
 
 
 class Widget:
@@ -100,12 +101,16 @@ def set_font(self, font):
         pass
 
     def set_color(self, color):
-        # By default, color can't be changed
-        pass
+        if color is None:
+            self.native.ForeColor = SystemColors.WindowText
+        else:
+            self.native.ForeColor = native_color(color)
 
     def set_background_color(self, color):
-        # By default, background color can't be changed.
-        pass
+        if color is None:
+            self.native.BackColor = SystemColors.Control
+        else:
+            self.native.BackColor = native_color(color)
 
     # INTERFACE
 
diff --git a/winforms/src/toga_winforms/widgets/box.py b/winforms/src/toga_winforms/widgets/box.py
index 71a2a4604c..3c84b98516 100644
--- a/winforms/src/toga_winforms/widgets/box.py
+++ b/winforms/src/toga_winforms/widgets/box.py
@@ -1,6 +1,3 @@
-from travertino.constants import TRANSPARENT
-
-from toga_winforms.colors import native_color
 from toga_winforms.libs import Point, Size, WinForms
 
 from .base import Widget
@@ -19,6 +16,9 @@ def set_bounds(self, x, y, width, height):
                 vertical_shift = (
                     self.frame.vertical_shift - self.interface.style.padding_top
                 )
+                # The outermost widget assumes the size of the viewport
+                width = self.viewport.width
+                height = self.viewport.height
             except AttributeError:
                 vertical_shift = self.interface.style.padding_top
             horizontal_shift = self.interface.style.padding_left
@@ -30,9 +30,3 @@ def set_bounds(self, x, y, width, height):
                 width + horizontal_size_adjustment, height + vertical_size_adjustment
             )
             self.native.Location = Point(x - horizontal_shift, y + vertical_shift)
-
-    def set_background_color(self, value):
-        if value:
-            self.native.BackColor = native_color(value)
-        else:
-            self.native.BackColor = native_color(TRANSPARENT)
diff --git a/winforms/src/toga_winforms/widgets/button.py b/winforms/src/toga_winforms/widgets/button.py
index 92578d4502..1c57a4ea0f 100644
--- a/winforms/src/toga_winforms/widgets/button.py
+++ b/winforms/src/toga_winforms/widgets/button.py
@@ -1,8 +1,8 @@
-from travertino.constants import TRANSPARENT
 from travertino.size import at_least
 
+from toga.colors import TRANSPARENT
 from toga_winforms.colors import native_color
-from toga_winforms.libs import WinForms
+from toga_winforms.libs import SystemColors, WinForms
 
 from .base import Widget
 
@@ -10,6 +10,7 @@
 class Button(Widget):
     def create(self):
         self.native = WinForms.Button()
+        self.native.AutoSizeMode = WinForms.AutoSizeMode.GrowAndShrink
         self.native.Click += self.winforms_click
         self.set_enabled(self.interface._enabled)
 
@@ -22,11 +23,16 @@ def get_text(self):
 
     def set_text(self, text):
         self.native.Text = text
-        self.rehint()
 
     def set_font(self, font):
         self.native.Font = font._impl.native
 
+    def set_background_color(self, color):
+        if color is None or color == TRANSPARENT:
+            self.native.BackColor = SystemColors.Control
+        else:
+            self.native.BackColor = native_color(color)
+
     def set_enabled(self, value):
         self.native.Enabled = self.interface._enabled
 
@@ -34,18 +40,6 @@ def set_on_press(self, handler):
         # No special handling required
         pass
 
-    def set_color(self, value):
-        if value:
-            self.native.ForeColor = native_color(value)
-        else:
-            self.native.ForeColor = native_color(TRANSPARENT)
-
-    def set_background_color(self, value):
-        if value:
-            self.native.BackColor = native_color(value)
-        else:
-            self.native.BackColor = native_color(TRANSPARENT)
-
     def rehint(self):
         # self.native.Size = Size(0, 0)
         # print("REHINT Button", self, self.native.PreferredSize)
diff --git a/winforms/src/toga_winforms/widgets/label.py b/winforms/src/toga_winforms/widgets/label.py
index 0272c502cc..85aafee14b 100644
--- a/winforms/src/toga_winforms/widgets/label.py
+++ b/winforms/src/toga_winforms/widgets/label.py
@@ -1,7 +1,5 @@
-from travertino.constants import TRANSPARENT
 from travertino.size import at_least
 
-from toga_winforms.colors import native_color
 from toga_winforms.libs import TextAlignment, WinForms
 
 from .base import Widget
@@ -10,6 +8,7 @@
 class Label(Widget):
     def create(self):
         self.native = WinForms.Label()
+        self.native.AutoSizeMode = WinForms.AutoSizeMode.GrowAndShrink
 
     def set_alignment(self, value):
         self.native.TextAlign = TextAlignment(value)
@@ -18,20 +17,7 @@ def set_text(self, value):
         self.native.Text = self.interface._text
 
     def set_font(self, font):
-        if font:
-            self.native.Font = font._impl.native
-
-    def set_color(self, value):
-        if value:
-            self.native.ForeColor = native_color(value)
-        else:
-            self.native.ForeColor = native_color(TRANSPARENT)
-
-    def set_background_color(self, value):
-        if value:
-            self.native.BackColor = native_color(value)
-        else:
-            self.native.BackColor = native_color(TRANSPARENT)
+        self.native.Font = font._impl.native
 
     def rehint(self):
         # Width & height of a label is known and fixed.
diff --git a/winforms/src/toga_winforms/window.py b/winforms/src/toga_winforms/window.py
index e3dc446020..126e11fd35 100644
--- a/winforms/src/toga_winforms/window.py
+++ b/winforms/src/toga_winforms/window.py
@@ -18,6 +18,7 @@ def width(self):
 
     @property
     def height(self):
+        # Treat `native=None` as a 0x0 viewport
         if self.native is None:
             return 0
         # Subtract any vertical shift of the frame. This is to allow
diff --git a/winforms/tests_backend/widgets/base.py b/winforms/tests_backend/widgets/base.py
index 909715a5c6..bbd7a10dab 100644
--- a/winforms/tests_backend/widgets/base.py
+++ b/winforms/tests_backend/widgets/base.py
@@ -1,6 +1,10 @@
 from System import EventArgs, Object
+from System.Drawing import SystemColors
 
-from .properties import toga_color
+from toga.colors import TRANSPARENT
+from toga.style.pack import JUSTIFY, LEFT
+
+from .properties import toga_color, toga_font
 
 
 class SimpleProbe:
@@ -17,22 +21,42 @@ def assert_container(self, container):
         else:
             raise ValueError(f"cannot find {self.native} in {container_native}")
 
+    def alignment_equivalent(self, actual, expected):
+        # Winforms doesn't have a "Justified" alignment; it falls back to LEFT
+        if expected == JUSTIFY:
+            assert actual == LEFT
+        else:
+            assert actual == expected
+        return True
+
     async def redraw(self):
         """Request a redraw of the app, waiting until that redraw has completed."""
-        # Refresh the layout
+        # TODO: Travertino/Pack doesn't force a layout refresh
+        # when properties such as flex or width are altered.
+        # For now, do a manual refresh.
         self.widget.window.content.refresh()
 
     @property
     def enabled(self):
         return self.native.Enabled
 
+    @property
+    def color(self):
+        if self.native.ForeColor == SystemColors.WindowText:
+            return None
+        else:
+            return toga_color(self.native.ForeColor)
+
     @property
     def background_color(self):
-        return toga_color(self.native.BackColor)
+        if self.native.BackColor == SystemColors.Control:
+            return TRANSPARENT
+        else:
+            return toga_color(self.native.BackColor)
 
     @property
-    def color(self):
-        return toga_color(self.native.ForeColor)
+    def font(self):
+        return toga_font(self.native.Font)
 
     @property
     def hidden(self):
diff --git a/winforms/tests_backend/widgets/button.py b/winforms/tests_backend/widgets/button.py
index a1c6fe343a..507cb30f82 100644
--- a/winforms/tests_backend/widgets/button.py
+++ b/winforms/tests_backend/widgets/button.py
@@ -1,7 +1,8 @@
 import System.Windows.Forms
-from pytest import skip
+from System.Drawing import SystemColors
 
 from .base import SimpleProbe
+from .properties import toga_color
 
 
 class ButtonProbe(SimpleProbe):
@@ -12,5 +13,8 @@ def text(self):
         return self.native.Text
 
     @property
-    def font(self):
-        skip("Font probe not implemented")
+    def background_color(self):
+        if self.native.BackColor == SystemColors.Control:
+            return None
+        else:
+            return toga_color(self.native.BackColor)
diff --git a/winforms/tests_backend/widgets/label.py b/winforms/tests_backend/widgets/label.py
index 9ce8c70da6..e814c92311 100644
--- a/winforms/tests_backend/widgets/label.py
+++ b/winforms/tests_backend/widgets/label.py
@@ -1,7 +1,7 @@
 import System.Windows.Forms
-from pytest import skip
 
 from .base import SimpleProbe
+from .properties import toga_alignment
 
 
 class LabelProbe(SimpleProbe):
@@ -11,10 +11,6 @@ class LabelProbe(SimpleProbe):
     def text(self):
         return self.native.Text
 
-    @property
-    def font(self):
-        skip("Font probe not implemented")
-
     @property
     def alignment(self):
-        skip("Alignment probe not implemented")
+        return toga_alignment(self.native.TextAlign)
diff --git a/winforms/tests_backend/widgets/properties.py b/winforms/tests_backend/widgets/properties.py
index f0eba27506..5e85ec343f 100644
--- a/winforms/tests_backend/widgets/properties.py
+++ b/winforms/tests_backend/widgets/properties.py
@@ -1,5 +1,56 @@
-from toga.colors import rgba
+from System.Drawing import (
+    Color,
+    ContentAlignment,
+    FontFamily,
+    SystemColors,
+    SystemFonts,
+)
+from travertino.fonts import Font
+
+from toga.colors import TRANSPARENT, rgba
+from toga.fonts import (
+    BOLD,
+    CURSIVE,
+    FANTASY,
+    ITALIC,
+    MESSAGE,
+    MONOSPACE,
+    NORMAL,
+    SANS_SERIF,
+    SERIF,
+    SYSTEM,
+)
+from toga.style.pack import CENTER, LEFT, RIGHT
 
 
 def toga_color(color):
-    return rgba(color.R, color.G, color.B, color.A / 255)
+    if color in {Color.Empty, SystemColors.Control}:
+        return TRANSPARENT
+    else:
+        return rgba(color.R, color.G, color.B, color.A / 255)
+
+
+def toga_font(font):
+    return Font(
+        family={
+            SystemFonts.DefaultFont.FontFamily.Name: SYSTEM,
+            SystemFonts.MenuFont.FontFamily.Name: MESSAGE,
+            FontFamily.GenericSerif.Name: SERIF,
+            FontFamily.GenericSansSerif.Name: SANS_SERIF,
+            "Comic Sans MS": CURSIVE,
+            "Impact": FANTASY,
+            FontFamily.GenericMonospace.Name: MONOSPACE,
+        }.get(str(font.Name), str(font.Name)),
+        size=int(font.SizeInPoints),
+        style=ITALIC if font.Italic else NORMAL,
+        variant=NORMAL,
+        weight=BOLD if font.Bold else NORMAL,
+    )
+
+
+def toga_alignment(alignment):
+    return {
+        ContentAlignment.MiddleLeft: LEFT,
+        ContentAlignment.MiddleRight: RIGHT,
+        ContentAlignment.MiddleCenter: CENTER,
+    }[alignment]