diff --git a/src/cocoa/toga_cocoa/widgets/icon.py b/src/cocoa/toga_cocoa/widgets/icon.py
index 0cf222373a..d7ef5985e3 100644
--- a/src/cocoa/toga_cocoa/widgets/icon.py
+++ b/src/cocoa/toga_cocoa/widgets/icon.py
@@ -1,8 +1,30 @@
+import os
+
+from toga import Icon as toga_Icon
 from toga_cocoa.libs import NSImage
 
 
 class Icon:
     def __init__(self, interface):
         self.interface = interface
-        interface.__impl = self
-        self.native = NSImage.alloc().initWithContentsOfFile(interface.filename)
+        self.interface._impl = self
+        file_path, file_extension = os.path.splitext(self.interface.filename)
+        valid_icon_extensions = ('.png', '.bmp', '.ico')
+
+        if file_extension == '.icns':
+            self.native = NSImage.alloc().initWithContentsOfFile(self.interface.filename)
+        elif os.path.isfile(file_path + '.icns'):
+            self.native = NSImage.alloc().initWithContentsOfFile(file_path + '.icns')
+        elif file_extension in valid_icon_extensions:
+            self.native = NSImage.alloc().initWithContentsOfFile(self.interface.filename)
+        elif os.path.isfile(file_path + '.png'):
+            self.native = NSImage.alloc().initWithContentsOfFile(file_path + '.png')
+        elif os.path.isfile(file_path + '.bmp'):
+            self.native = NSImage.alloc().initWithContentsOfFile(file_path + '.bmp')
+        else:
+            print("[Cocoa] No valid icon format available for {}; "
+                  "fall back on Tiberius instead".format(
+                self.interface.filename))
+            tiberius_file = toga_Icon.TIBERIUS_ICON.filename + '.icns'
+            self.interface.icon = toga_Icon.TIBERIUS_ICON
+            self.native = NSImage.alloc().initWithContentsOfFile(tiberius_file)
diff --git a/src/core/tests/test_app.py b/src/core/tests/test_app.py
index 8fa72c84df..9a97871537 100644
--- a/src/core/tests/test_app.py
+++ b/src/core/tests/test_app.py
@@ -34,7 +34,7 @@ def test_app_icon(self):
         self.assertEqual(self.app.icon, self.app.default_icon)
 
         # Set the icon to a different resource
-        self.app.icon = "other"
+        self.app.icon = "other.icns"
         self.assertEqual(self.app.icon.path, "other.icns")
 
     def test_app_app_id(self):
diff --git a/src/core/toga/command.py b/src/core/toga/command.py
index bbaccb0935..88216ddc4f 100644
--- a/src/core/toga/command.py
+++ b/src/core/toga/command.py
@@ -76,6 +76,8 @@ def enabled(self, value):
         self._enabled = value
         for widget in self._widgets:
             widget.enabled = value
+        if self._impl is not None:
+            self._impl.enabled = value
 
 
 GROUP_BREAK = object()
diff --git a/src/core/toga/resources/tiberius.ico b/src/core/toga/resources/tiberius.ico
new file mode 100644
index 0000000000..aa3492f61b
Binary files /dev/null and b/src/core/toga/resources/tiberius.ico differ
diff --git a/src/core/toga/widgets/icon.py b/src/core/toga/widgets/icon.py
index 81de7af6b2..72c63dfa16 100644
--- a/src/core/toga/widgets/icon.py
+++ b/src/core/toga/widgets/icon.py
@@ -26,10 +26,7 @@ class Icon:
     """
 
     def __init__(self, path, system=False):
-        if os.path.splitext(path)[1] in ('.png', '.icns', '.bmp'):
-            self.path = path
-        else:
-            self.path = path + '.icns'
+        self.path = path
 
         self.system = system
 
diff --git a/src/winforms/toga_winforms/app.py b/src/winforms/toga_winforms/app.py
index d8663659de..bb89f65204 100644
--- a/src/winforms/toga_winforms/app.py
+++ b/src/winforms/toga_winforms/app.py
@@ -1,4 +1,8 @@
-from .libs import Threading, WinForms
+import sys
+
+import toga
+
+from .libs import Threading, WinForms, add_handler
 from .window import Window
 
 
@@ -17,21 +21,55 @@ def __init__(self, interface):
     def create(self):
         self.native = WinForms.Application
 
-        # self.native.setApplicationIconImage_(self.icon.native)
-
-        # Set the menu for the app.
-        # self.native.setMainMenu_(self.menu)
+        self.interface.commands.add(
+            toga.Command(None, 'About ' + self.interface.name, group=toga.Group.HELP),
+            toga.Command(None, 'Preferences', group=toga.Group.FILE),
+            # Quit should always be the last item, in a section on it's own
+            toga.Command(lambda s: self.exit(), 'Exit ' + self.interface.name, shortcut='q', group=toga.Group.FILE,
+                         section=sys.maxsize),
+            toga.Command(None, 'Visit homepage', group=toga.Group.HELP)
+        )
 
         # Call user code to populate the main window
         self.interface.startup()
+        self._menu_items = {}
+        self.create_menus()
+        self.interface.main_window._impl.native.Icon = \
+            self.interface.icon.bind(self.interface.factory).native
+
+    def create_menus(self):
+        toga.Group.FILE.order = 0
+        # Only create the menu if the menu item index has been created.
+        if hasattr(self, '_menu_items'):
+            menubar = WinForms.MenuStrip()
+            submenu = None
+            for cmd in self.interface.commands:
+                if cmd == toga.GROUP_BREAK:
+                    menubar.Items.Add(submenu)
+                    submenu = None
+                elif cmd == toga.SECTION_BREAK:
+                    submenu.DropDownItems.Add('-')
+                else:
+                    if submenu is None:
+                        submenu = WinForms.ToolStripMenuItem(cmd.group.label)
+                    item = WinForms.ToolStripMenuItem(cmd.label)
+                    if cmd.action:
+                        item.Click += add_handler(cmd)
+                    else:
+                        item.Enabled = False
+                    cmd._widgets.append(item)
+                    self._menu_items[item] = cmd
+                    submenu.DropDownItems.Add(item)
+            if submenu:
+                menubar.Items.Add(submenu)
+            self.interface.main_window._impl.native.Controls.Add(menubar)
+            self.interface.main_window._impl.native.MainMenuStrip = menubar
+        self.interface.main_window.content.refresh()
 
     def open_document(self, fileURL):
         '''Add a new document to this app.'''
         print("STUB: If you want to handle opening documents, implement App.open_document(fileURL)")
 
-    def create_menus(self):
-        self.interface.factory.not_implemented('App.create_menus()')
-
     def run_app(self):
         self.create()
         self.native.Run(self.interface.main_window._impl.native)
@@ -43,4 +81,4 @@ def main_loop(self):
         thread.Join()
 
     def exit(self):
-        self.interface.factory.not_implemented('App.exit()')
+        self.native.Exit()
diff --git a/src/winforms/toga_winforms/command.py b/src/winforms/toga_winforms/command.py
index 3bbbe7d62c..4fd4d2c588 100644
--- a/src/winforms/toga_winforms/command.py
+++ b/src/winforms/toga_winforms/command.py
@@ -1,10 +1,14 @@
-#from .widgets.icon import Icon
+from toga.widgets.icon import Icon as CoreIcon
 
 class Command:
     def __init__(self, interface):
         self.interface = interface
-
-        # if self.interface.icon_id:
-        #     self.icon = Icon.load(self.interface.icon_id)
-        # else:
-        #     self.icon = None
+        self.native = None
+        if self.interface.icon_id:
+            # If icon_id is an icon, not a filepath
+            if type(self.interface.icon_id) is not str:
+                self.interface.icon = self.interface.icon_id
+            else:
+                self.interface.icon = CoreIcon(self.interface.icon_id)
+        else:
+            self.interface.icon = None
diff --git a/src/winforms/toga_winforms/libs.py b/src/winforms/toga_winforms/libs.py
index f1bdd2721d..fe71ffa4de 100644
--- a/src/winforms/toga_winforms/libs.py
+++ b/src/winforms/toga_winforms/libs.py
@@ -8,7 +8,8 @@
 from System import Convert
 from System import Threading
 from System import Uri
-from System.Drawing import Size, Point, Color, ContentAlignment
+from System.Drawing import Size, Point, Color, ContentAlignment, Bitmap
+from System.Drawing import Icon as WinIcon
 
 
 def TextAlignment(value):
@@ -18,3 +19,10 @@ def TextAlignment(value):
         CENTER: ContentAlignment.MiddleCenter,
         JUSTIFY: ContentAlignment.MiddleLeft,
     }[value]
+
+
+def add_handler(cmd):
+    action = cmd.action
+    def handler(sender, event):
+        return action(None)
+    return handler
diff --git a/src/winforms/toga_winforms/widgets/icon.py b/src/winforms/toga_winforms/widgets/icon.py
index bce10585bf..5c5f8bff26 100644
--- a/src/winforms/toga_winforms/widgets/icon.py
+++ b/src/winforms/toga_winforms/widgets/icon.py
@@ -1,8 +1,41 @@
-# from ..libs import NSImage
+import os
+
+from toga import Icon as toga_Icon
+from toga_winforms.libs import Bitmap, WinIcon
 
 
 class Icon:
     def __init__(self, interface):
+
+        def create_icon_from_file(filename):
+            icon_bitmap = Bitmap(self.interface.filename)
+            icon_handle = icon_bitmap.GetHicon()
+            return WinIcon.FromHandle(icon_handle)
+
         self.interface = interface
-        interface._impl = self
-        # self.native = NSImage.alloc().initWithContentsOfFile(interface.filename)
+        self.interface._impl = self
+        valid_icon_extensions = ('.png', '.bmp', '.ico')
+        file_path, file_extension = os.path.splitext(self.interface.filename)
+
+        if file_extension == '.ico':
+            self.native = WinIcon(self.interface.filename)
+
+        elif os.path.isfile(file_path + '.ico'):
+            self.native = WinIcon(file_path + '.ico')
+
+        elif file_extension in valid_icon_extensions:
+            self.native = create_icon_from_file(self.interface.filename)
+
+        elif os.path.isfile(file_path + '.png'):
+            self.native = create_icon_from_file(file_path + '.png')
+
+        elif os.path.isfile(file_path + '.bmp'):
+            self.native = create_icon_from_file(file_path + '.bmp')
+
+        else:
+            print("[Winforms] No valid icon format available for {}; "
+                  "fall back on Tiberius instead".format(
+                self.interface.filename))
+            tiberius_file = toga_Icon.TIBERIUS_ICON.filename + '.ico'
+            self.interface.icon = toga_Icon.TIBERIUS_ICON
+            self.native = WinIcon(tiberius_file)
diff --git a/src/winforms/toga_winforms/widgets/webview.py b/src/winforms/toga_winforms/widgets/webview.py
index b139ec796b..e1253c0c50 100644
--- a/src/winforms/toga_winforms/widgets/webview.py
+++ b/src/winforms/toga_winforms/widgets/webview.py
@@ -1,6 +1,6 @@
 from travertino.size import at_least
 
-from toga_winforms.libs import WinForms
+from toga_winforms.libs import WinForms, Uri
 
 from .base import Widget
 
diff --git a/src/winforms/toga_winforms/window.py b/src/winforms/toga_winforms/window.py
index bcae2ac4a2..667d60966d 100644
--- a/src/winforms/toga_winforms/window.py
+++ b/src/winforms/toga_winforms/window.py
@@ -1,7 +1,7 @@
 from toga import GROUP_BREAK, SECTION_BREAK
 from travertino.layout import Viewport
 
-from .libs import WinForms, Size
+from .libs import WinForms, Size, add_handler
 
 
 class WinFormsViewport:
@@ -36,14 +36,21 @@ def create(self):
         self.toolbar_items = None
 
     def create_toolbar(self):
-        self.toolbar_native = WinForms.ToolStrip()
+        self.toolbar_native = WinForms.MenuStrip()
         for cmd in self.interface.toolbar:
             if cmd == GROUP_BREAK:
                 item = WinForms.ToolStripSeparator()
             elif cmd == SECTION_BREAK:
                 item = WinForms.ToolStripSeparator()
             else:
-                item = WinForms.ToolStripButton()
+                cmd.native = cmd.bind(self.interface.factory)
+                native_icon = cmd.icon.bind(self.interface.factory).native
+                if cmd.icon is not None:
+                    item = WinForms.ToolStripMenuItem(cmd.label, native_icon.ToBitmap())
+                else:
+                    item = WinForms.ToolStripMenuItem(cmd.label)
+
+                item.Click += add_handler(cmd)
             self.toolbar_native.Items.Add(item)
 
     def set_position(self, position):
@@ -58,15 +65,22 @@ def set_app(self, app):
     @property
     def vertical_shift(self):
         # vertical shift is the toolbar height or 0
+        result = 0
         try:
-            return self.native.interface._impl.toolbar_native.Height
+            result += self.native.interface._impl.toolbar_native.Height
         except AttributeError:
-            return 0
+            pass
+        try:
+            result += self.native.interface._impl.native.MainMenuStrip.Height
+        except AttributeError:
+            pass
+        return result
 
     def set_content(self, widget):
         if self.toolbar_native:
             self.native.Controls.Add(self.toolbar_native)
-
+            # Create the lookup table of menu items,
+            # then force the creation of the menus.
         self.native.Controls.Add(widget.native)
 
         # Set the widget's viewport to be based on the window's content.