diff --git a/src/app/dev/DevToys.Core/AppHelper.cs b/src/app/dev/DevToys.Core/AppHelper.cs
index 6d3146daee..f64fa9d812 100644
--- a/src/app/dev/DevToys.Core/AppHelper.cs
+++ b/src/app/dev/DevToys.Core/AppHelper.cs
@@ -109,14 +109,14 @@ var assemblyInformationalVersion
                             .GetExecutingAssembly()
                             .GetCustomAttribute(typeof(AssemblyInformationalVersionAttribute))!;
 
-                    string currentVersion
+                    string currentVersionString
                         = assemblyInformationalVersion.InformationalVersion
                             .TrimStart('v')
                             .Replace("-alpha", string.Empty)
                             .Replace("-beta", string.Empty)
                             .Replace("-preview", string.Empty)
                             .Replace("-pre", string.Empty);
-                    string? releaseVersion
+                    string? gitHubVersionString
                         = potentialRelease.Name?
                             .TrimStart('v')
                             .Replace("-alpha", string.Empty)
@@ -124,9 +124,14 @@ string currentVersion
                             .Replace("-preview", string.Empty)
                             .Replace("-pre", string.Empty);
 
-                    if (!string.IsNullOrEmpty(releaseVersion) && !string.IsNullOrEmpty(currentVersion))
+                    if (!string.IsNullOrEmpty(gitHubVersionString) && !string.IsNullOrEmpty(currentVersionString))
                     {
-                        if (new System.Version(releaseVersion) > new System.Version(currentVersion))
+                        var gitHubReleaseVersion = new System.Version(gitHubVersionString);
+                        var currentVersion = new System.Version(currentVersionString);
+
+                        if (gitHubReleaseVersion.Major > currentVersion.Major
+                            || (gitHubReleaseVersion.Major == currentVersion.Major && gitHubReleaseVersion.Minor > currentVersion.Minor)
+                            || (gitHubReleaseVersion.Major == currentVersion.Major && gitHubReleaseVersion.Minor == currentVersion.Minor && gitHubReleaseVersion.Build > currentVersion.Build))
                         {
                             return true;
                         }
diff --git a/src/app/tests/DevToys.UnitTests/Core/AppHelperTests.cs b/src/app/tests/DevToys.UnitTests/Core/AppHelperTests.cs
index 159a6188be..38c2ddbfee 100644
--- a/src/app/tests/DevToys.UnitTests/Core/AppHelperTests.cs
+++ b/src/app/tests/DevToys.UnitTests/Core/AppHelperTests.cs
@@ -102,6 +102,34 @@ GitHubRelease[] releases
         result.Should().BeFalse();
     }
 
+    [Fact]
+    public async Task CheckForUpdate_Preview_NoUpdate2_Async()
+    {
+        GitHubRelease[] releases
+            = [
+                new GitHubRelease
+                {
+                    Draft = false,
+                    PreRelease = true,
+                    Name = "v0.0.0"
+                },
+              ];
+        string releasesJson = JsonSerializer.Serialize(releases);
+
+        var mockWebClientService = new Mock<IWebClientService>();
+        mockWebClientService
+            .Setup(service => service.SafeGetStringAsync(It.IsAny<Uri>(), CancellationToken.None))
+            .ReturnsAsync(releasesJson);
+
+        var mockVersionService = new Mock<IVersionService>();
+        mockVersionService
+            .Setup(service => service.IsPreviewVersion())
+            .Returns(true);
+
+        bool result = await AppHelper.CheckForUpdateAsync(mockWebClientService.Object, mockVersionService.Object, CancellationToken.None);
+        result.Should().BeFalse();
+    }
+
     [Fact]
     public async Task CheckForUpdate_StableAsync()
     {