diff --git a/src/StaticWebAssetsSdk/Tasks/GenerateStaticWebAssetsManifest.cs b/src/StaticWebAssetsSdk/Tasks/GenerateStaticWebAssetsManifest.cs
index 1bf04ed48714..af3d46ff6caf 100644
--- a/src/StaticWebAssetsSdk/Tasks/GenerateStaticWebAssetsManifest.cs
+++ b/src/StaticWebAssetsSdk/Tasks/GenerateStaticWebAssetsManifest.cs
@@ -158,7 +158,7 @@ private void PersistManifest(StaticWebAssetsManifest manifest)
 
         foreach (var asset in assets)
         {
-            var targetPath = asset.ComputeTargetPath("", '/');
+            var targetPath = asset.ComputeTargetPath("", '/', StaticWebAssetTokenResolver.Instance);
 
             if (result.TryGetValue(targetPath, out var existing))
             {
diff --git a/test/Microsoft.NET.Sdk.StaticWebAssets.Tests/StaticWebAssets/StaticWebAssetTest.cs b/test/Microsoft.NET.Sdk.StaticWebAssets.Tests/StaticWebAssets/StaticWebAssetTest.cs
new file mode 100644
index 000000000000..83f5d3bb163a
--- /dev/null
+++ b/test/Microsoft.NET.Sdk.StaticWebAssets.Tests/StaticWebAssets/StaticWebAssetTest.cs
@@ -0,0 +1,187 @@
+// Licensed to the .NET Foundation under one or more agreements.
+// The .NET Foundation licenses this file to you under the MIT license.
+
+#nullable disable
+
+using Microsoft.AspNetCore.StaticWebAssets.Tasks;
+
+namespace Microsoft.NET.Sdk.StaticWebAssets.Tests.StaticWebAssets;
+
+public class StaticWebAssetTest
+{
+    [Fact]
+    public void ValidateAssetGroup_SingleAsset_ReturnsTrue()
+    {
+        var asset = CreateAsset("wwwroot/app.js", "app.js", "All", "All");
+        var group = (asset, (StaticWebAsset)null, (IReadOnlyList<StaticWebAsset>)null);
+
+        var result = StaticWebAsset.ValidateAssetGroup("app.js", group, out var reason);
+
+        Assert.True(result);
+        Assert.Null(reason);
+    }
+
+    [Fact]
+    public void ValidateAssetGroup_TwoAssetsFromDifferentProjects_ReturnsFalse()
+    {
+        var asset1 = CreateAsset("wwwroot/app.js", "app.js", "All", "All", sourceId: "Project1");
+        var asset2 = CreateAsset("wwwroot/app.js", "app.js", "All", "All", sourceId: "Project2");
+        var group = (asset1, asset2, (IReadOnlyList<StaticWebAsset>)null);
+
+        var result = StaticWebAsset.ValidateAssetGroup("app.js", group, out var reason);
+
+        Assert.False(result);
+        Assert.Contains("different projects", reason);
+    }
+
+    [Fact]
+    public void ValidateAssetGroup_TwoAllAssetsFromSameProject_ReturnsFalse()
+    {
+        var asset1 = CreateAsset("wwwroot/app.js", "app.js", "All", "All");
+        var asset2 = CreateAsset("obj/app.js", "app.js", "All", "All");
+        var group = (asset1, asset2, (IReadOnlyList<StaticWebAsset>)null);
+
+        var result = StaticWebAsset.ValidateAssetGroup("app.js", group, out var reason);
+
+        Assert.False(result);
+        Assert.Contains("'All' assets", reason);
+    }
+
+    [Fact]
+    public void ValidateAssetGroup_BuildAndPublishAssetsFromSameProject_ReturnsTrue()
+    {
+        var buildAsset = CreateAsset("wwwroot/app.js", "app.js", "Build", "All");
+        var publishAsset = CreateAsset("obj/app.js", "app.js", "Publish", "All");
+        var group = (buildAsset, publishAsset, (IReadOnlyList<StaticWebAsset>)null);
+
+        var result = StaticWebAsset.ValidateAssetGroup("app.js", group, out var reason);
+
+        Assert.True(result);
+        Assert.Null(reason);
+    }
+
+    [Fact]
+    public void ComputeTargetPath_WithoutTokenResolver_KeepsTokensInPath()
+    {
+        var asset = CreateAsset(
+            "wwwroot/MyApp.styles.css",
+            "MyApp.styles#[.{fingerprint}]?.css",
+            "All",
+            "All");
+        asset.Fingerprint = "abc123";
+
+        var targetPath = asset.ComputeTargetPath("", '/');
+
+        Assert.Equal("MyApp.styles#[.{fingerprint}]?.css", targetPath);
+    }
+
+    [Fact]
+    public void ComputeTargetPath_WithTokenResolver_ReplacesOptionalTokens()
+    {
+        var asset = CreateAsset(
+            "wwwroot/MyApp.styles.css",
+            "MyApp.styles#[.{fingerprint}]?.css",
+            "All",
+            "All");
+        asset.Fingerprint = "abc123";
+
+        var targetPath = asset.ComputeTargetPath("", '/', StaticWebAssetTokenResolver.Instance);
+
+        Assert.Equal("MyApp.styles.css", targetPath);
+    }
+
+    [Fact]
+    public void TwoAssetsWithDifferentPatternsResolveToSameTargetPath_AfterTokenReplacement()
+    {
+        var discoveredAsset = CreateAsset(
+            "wwwroot/MyApp.styles.css",
+            "MyApp.styles#[.{fingerprint}]?.css",
+            "All",
+            "All");
+        discoveredAsset.Fingerprint = "abc123";
+
+        var computedAsset = CreateAsset(
+            "obj/scopedcss/bundle/MyApp.styles.css",
+            "MyApp#[.{fingerprint}]?.styles.css",
+            "All",
+            "CurrentProject");
+        computedAsset.Fingerprint = "xyz789";
+
+        var path1WithTokens = discoveredAsset.ComputeTargetPath("", '/');
+        var path2WithTokens = computedAsset.ComputeTargetPath("", '/');
+
+        Assert.NotEqual(path1WithTokens, path2WithTokens);
+        Assert.Equal("MyApp.styles#[.{fingerprint}]?.css", path1WithTokens);
+        Assert.Equal("MyApp#[.{fingerprint}]?.styles.css", path2WithTokens);
+
+        var path1Resolved = discoveredAsset.ComputeTargetPath("", '/', StaticWebAssetTokenResolver.Instance);
+        var path2Resolved = computedAsset.ComputeTargetPath("", '/', StaticWebAssetTokenResolver.Instance);
+
+        Assert.Equal("MyApp.styles.css", path1Resolved);
+        Assert.Equal("MyApp.styles.css", path2Resolved);
+        Assert.Equal(path1Resolved, path2Resolved);
+    }
+
+    [Fact]
+    public void ValidateAssetGroup_DetectsConflict_WhenAssetsHaveDifferentPatterns_ButSameResolvedPath()
+    {
+        var discoveredAsset = CreateAsset(
+            "wwwroot/MyApp.styles.css",
+            "MyApp.styles#[.{fingerprint}]?.css",
+            "All",
+            "All");
+        discoveredAsset.Fingerprint = "abc123";
+
+        var computedAsset = CreateAsset(
+            "obj/scopedcss/bundle/MyApp.styles.css",
+            "MyApp#[.{fingerprint}]?.styles.css",
+            "All",
+            "CurrentProject");
+        computedAsset.Fingerprint = "xyz789";
+
+        var group = (discoveredAsset, computedAsset, (IReadOnlyList<StaticWebAsset>)null);
+        var result = StaticWebAsset.ValidateAssetGroup("MyApp.styles.css", group, out var reason);
+
+        Assert.False(result);
+        Assert.Contains("'All' assets", reason);
+    }
+
+    private static StaticWebAsset CreateAsset(
+        string itemSpec,
+        string relativePath,
+        string assetKind,
+        string assetMode,
+        string sourceId = "MyProject",
+        string sourceType = "Computed")
+    {
+        var result = new StaticWebAsset
+        {
+            Identity = Path.GetFullPath(itemSpec),
+            SourceId = sourceId,
+            SourceType = sourceType,
+            ContentRoot = Directory.GetCurrentDirectory(),
+            BasePath = "base",
+            RelativePath = relativePath,
+            AssetKind = assetKind,
+            AssetMode = assetMode,
+            AssetRole = "Primary",
+            AssetMergeBehavior = StaticWebAsset.MergeBehaviors.PreferTarget,
+            AssetMergeSource = "",
+            RelatedAsset = "",
+            AssetTraitName = "",
+            AssetTraitValue = "",
+            CopyToOutputDirectory = "Never",
+            CopyToPublishDirectory = "PreserveNewest",
+            OriginalItemSpec = itemSpec,
+            Integrity = "integrity",
+            Fingerprint = "fingerprint",
+            LastWriteTime = new DateTimeOffset(2023, 10, 1, 0, 0, 0, TimeSpan.Zero),
+            FileLength = 10,
+        };
+
+        result.ApplyDefaults();
+        result.Normalize();
+
+        return result;
+    }
+}