diff --git a/src/Core/src/Fonts/FontManager.Windows.cs b/src/Core/src/Fonts/FontManager.Windows.cs
index 6973f61ea17e..5090dd7b0863 100644
--- a/src/Core/src/Fonts/FontManager.Windows.cs
+++ b/src/Core/src/Fonts/FontManager.Windows.cs
@@ -5,6 +5,8 @@
 using System.IO;
 using Microsoft.Extensions.Logging;
 using Microsoft.Graphics.Canvas.Text;
+using Microsoft.Maui.ApplicationModel;
+using Microsoft.Maui.Storage;
 using Microsoft.UI.Xaml.Media;
 
 namespace Microsoft.Maui
@@ -146,16 +148,20 @@ IEnumerable<string> GetAllFontPossibilities(string fontFamily)
 			{
 				var fontUri = new Uri(fontFile, UriKind.RelativeOrAbsolute);
 
-				// CanvasFontSet only supports ms-appx:// and ms-appdata:// font URIs
-				if (fontUri.IsAbsoluteUri && (fontUri.Scheme == "ms-appx" || fontUri.Scheme == "ms-appdata"))
+				// unpackaged apps can't load files using packaged schemes
+				if (!AppInfoUtils.IsPackagedApp)
 				{
-					using (var fontSet = new CanvasFontSet(fontUri))
+					var path = fontUri.AbsolutePath.TrimStart('/');
+					if (FileSystemUtils.TryGetAppPackageFileUri(path, out var uri))
+						fontUri = new Uri(uri, UriKind.RelativeOrAbsolute);
+				}
+
+				using (var fontSet = new CanvasFontSet(fontUri))
+				{
+					if (fontSet.Fonts.Count != 0)
 					{
-						if (fontSet.Fonts.Count != 0)
-						{
-							var props = fontSet.GetPropertyValues(CanvasFontPropertyIdentifier.FamilyName);
-							return props.Length == 0 ? null : props[0].Value;
-						}
+						var props = fontSet.GetPropertyValues(CanvasFontPropertyIdentifier.FamilyName);
+						return props.Length == 0 ? null : props[0].Value;
 					}
 				}
 
diff --git a/src/Core/tests/DeviceTests/Core.DeviceTests.csproj b/src/Core/tests/DeviceTests/Core.DeviceTests.csproj
index 38b4ce0f3b8a..f9609cc3b58f 100644
--- a/src/Core/tests/DeviceTests/Core.DeviceTests.csproj
+++ b/src/Core/tests/DeviceTests/Core.DeviceTests.csproj
@@ -17,6 +17,15 @@
     <ApplicationVersion>1</ApplicationVersion>
   </PropertyGroup>
 
+  <PropertyGroup>
+    <!--
+      Uncomment the below to enabled unpackaged apps and change the
+      value of the "commandName" in the Properties\launchSettings.json
+      from "MsixPackage" to "Project".
+    -->
+    <!-- <WindowsPackageType>None</WindowsPackageType> -->
+  </PropertyGroup>
+
   <ItemGroup>
     <MauiIcon Include="Resources\appicon.svg" ForegroundFile="Resources\appiconfg.svg" Color="#512BD4" />
     <MauiSplashScreen Include="Resources\appiconfg.svg" Color="#512BD4" BaseSize="128,128" />
@@ -45,10 +54,10 @@
     <None Include="@(Compile)" />
   </ItemGroup>
   <ItemGroup Condition="$(TargetFramework.Contains('-windows'))">
-    <Compile Remove="Handlers\Fonts\*.cs" />
     <Compile Remove="Handlers\Image\*.cs" />
     <Compile Remove="Handlers\ImageButton\*.cs" />
     <Compile Remove="Handlers\ShapeView\*.cs" />
+    <Content Include="Platforms\Windows\Assets\**" Link="Assets\%(RecursiveDir)%(Filename)%(Extension)" CopyToOutputDirectory="PreserveNewest" />
   </ItemGroup>
   <ItemGroup Condition="!$(TargetFramework.Contains('-android'))">
     <Compile Remove="**\*.Android.cs" />
diff --git a/src/Core/tests/DeviceTests/Platforms/Windows/Assets/Fonts/insubfolder.ttf b/src/Core/tests/DeviceTests/Platforms/Windows/Assets/Fonts/insubfolder.ttf
new file mode 100644
index 000000000000..051a88fe379a
Binary files /dev/null and b/src/Core/tests/DeviceTests/Platforms/Windows/Assets/Fonts/insubfolder.ttf differ
diff --git a/src/Core/tests/DeviceTests/Services/FontManagerTests.Windows.cs b/src/Core/tests/DeviceTests/Services/FontManagerTests.Windows.cs
new file mode 100644
index 000000000000..75d75650c1a8
--- /dev/null
+++ b/src/Core/tests/DeviceTests/Services/FontManagerTests.Windows.cs
@@ -0,0 +1,40 @@
+using System;
+using System.Threading.Tasks;
+using Xunit;
+
+namespace Microsoft.Maui.DeviceTests;
+
+public partial class FontManagerTests : TestBase
+{
+	[Theory]
+	[InlineData("dokdo_regular", "ms-appx:///dokdo_regular.ttf#Dokdo")]
+	[InlineData("dokdo_regular.ttf", "ms-appx:///dokdo_regular.ttf#Dokdo")]
+	[InlineData("dokdo_regular#dokdo", "ms-appx:///dokdo_regular.ttf#Dokdo")]
+	[InlineData("dokdo_regular.ttf#dokdo", "ms-appx:///dokdo_regular.ttf#Dokdo")]
+	[InlineData("myalias", "ms-appx:///dokdo_regular.ttf#Dokdo")]
+	public Task CanLoadFonts(string fontName, string actualFontFamily) =>
+		InvokeOnMainThreadAsync(() =>
+		{
+			var registrar = new FontRegistrar(fontLoader: null);
+			registrar.Register("dokdo_regular.ttf", "myalias");
+			var manager = new FontManager(registrar);
+
+			var actual = manager.GetFontFamily(Font.OfSize(fontName, 12, FontWeight.Regular));
+
+			Assert.Equal(actualFontFamily, actual.Source);
+		});
+
+	// TODO: this is not going to work in unpackaged
+	[Fact]
+	public Task CanLoadEmbeddedFont() =>
+		InvokeOnMainThreadAsync(() =>
+		{
+			var registrar = new FontRegistrar(new EmbeddedFontLoader());
+			registrar.Register("dokdo_regular.ttf", "myalias", GetType().Assembly);
+			var manager = new FontManager(registrar);
+
+			var actual = manager.GetFontFamily(Font.OfSize("myalias", 12, FontWeight.Regular));
+
+			Assert.Equal("ms-appdata:///local/fonts/dokdo_regular.ttf#Dokdo", actual.Source);
+		});
+}
diff --git a/src/Essentials/src/FileSystem/FileSystem.uwp.cs b/src/Essentials/src/FileSystem/FileSystem.uwp.cs
index 9719ed661fef..9146e54fa71d 100644
--- a/src/Essentials/src/FileSystem/FileSystem.uwp.cs
+++ b/src/Essentials/src/FileSystem/FileSystem.uwp.cs
@@ -50,31 +50,6 @@ Task<bool> PlatformAppPackageFileExistsAsync(string filename)
 		}
 	}
 
-	static partial class FileSystemUtils
-	{
-		public static bool AppPackageFileExists(string filename)
-		{
-			var file = PlatformGetFullAppPackageFilePath(filename);
-			return File.Exists(file);
-		}
-
-		public static string PlatformGetFullAppPackageFilePath(string filename)
-		{
-			if (filename == null)
-				throw new ArgumentNullException(nameof(filename));
-
-			filename = NormalizePath(filename);
-
-			string root;
-			if (AppInfoUtils.IsPackagedApp)
-				root = Package.Current.InstalledLocation.Path;
-			else
-				root = AppContext.BaseDirectory;
-
-			return Path.Combine(root, filename);
-		}
-	}
-
 	public partial class FileBase
 	{
 		internal FileBase(IStorageFile file)
diff --git a/src/Essentials/src/FileSystem/FileSystemUtils.uwp.cs b/src/Essentials/src/FileSystem/FileSystemUtils.uwp.cs
new file mode 100644
index 000000000000..9d2cd968f76d
--- /dev/null
+++ b/src/Essentials/src/FileSystem/FileSystemUtils.uwp.cs
@@ -0,0 +1,52 @@
+#nullable enable
+using System;
+using System.Diagnostics.CodeAnalysis;
+using System.IO;
+using Microsoft.Maui.ApplicationModel;
+using Package = Windows.ApplicationModel.Package;
+
+namespace Microsoft.Maui.Storage
+{
+	static partial class FileSystemUtils
+	{
+		public static bool AppPackageFileExists(string filename)
+		{
+			var file = PlatformGetFullAppPackageFilePath(filename);
+			return File.Exists(file);
+		}
+
+		public static string PlatformGetFullAppPackageFilePath(string filename)
+		{
+			if (filename is null)
+				throw new ArgumentNullException(nameof(filename));
+
+			filename = NormalizePath(filename);
+
+			string root;
+			if (AppInfoUtils.IsPackagedApp)
+				root = Package.Current.InstalledLocation.Path;
+			else
+				root = AppContext.BaseDirectory;
+
+			return Path.Combine(root, filename);
+		}
+
+		public static bool TryGetAppPackageFileUri(string filename, [NotNullWhen(true)] out string? uri)
+		{
+			var path = PlatformGetFullAppPackageFilePath(filename);
+
+			if (File.Exists(path))
+			{
+				if (AppInfoUtils.IsPackagedApp)
+					uri = $"ms-appx:///{filename.Replace('\\', '/')}";
+				else
+					uri = $"file:///{path.Replace('\\', '/')}";
+
+				return true;
+			}
+
+			uri = null;
+			return false;
+		}
+	}
+}