diff --git a/src/WingetCreateCLI/Commands/UpdateCommand.cs b/src/WingetCreateCLI/Commands/UpdateCommand.cs
index da0377a2..a9961457 100644
--- a/src/WingetCreateCLI/Commands/UpdateCommand.cs
+++ b/src/WingetCreateCLI/Commands/UpdateCommand.cs
@@ -239,6 +239,20 @@ await this.UpdateManifestsInteractively(initialManifests) :
                         return false;
                     }
 
+                    if (!this.Replace)
+                    {
+                        // Updated manifests will always be in multi-manifest format so no need to check for singleton manifest.
+                        string updatedVersion = updatedManifests.VersionManifest.PackageVersion;
+                        string originalVersion = originalManifests.VersionManifest != null ? originalManifests.VersionManifest.PackageVersion : originalManifests.SingletonManifest.PackageVersion;
+
+                        if (WinGetUtil.CompareVersions(updatedVersion, originalVersion) != 0 && AreInstallerUrlsVanityUrls(originalManifests, updatedManifests))
+                        {
+                            Logger.InfoLocalized(nameof(Resources.AutoReplacingPreviousVersion_Message));
+                            Console.WriteLine();
+                            this.Replace = true;
+                        }
+                    }
+
                     return await this.LoadGitHubClient(true)
                         ? (commandEvent.IsSuccessful = await this.GitHubSubmitManifests(
                             updatedManifests,
@@ -638,6 +652,27 @@ private static void DisplayManifestsAsMenuSelection(Manifests manifests)
             }
         }
 
+        private static bool AreInstallerUrlsVanityUrls(Manifests baseManifest, Manifests newManifest)
+        {
+            List<Installer> newInstallers = newManifest.InstallerManifest.Installers;
+
+            // All installer URLs in the new manifest must have a matching installer URL in the base manifest.
+            foreach (Installer installer in newInstallers)
+            {
+                if (baseManifest.InstallerManifest != null && !baseManifest.InstallerManifest.Installers.Any(i => i.InstallerUrl == installer.InstallerUrl))
+                {
+                    return false;
+                }
+
+                if (baseManifest.SingletonManifest != null && !baseManifest.SingletonManifest.Installers.Any(i => i.InstallerUrl == installer.InstallerUrl))
+                {
+                    return false;
+                }
+            }
+
+            return true;
+        }
+
         private string ObtainMatchingRelativeFilePath(string oldRelativeFilePath, string directory, string archiveName)
         {
             string fileName = Path.GetFileName(oldRelativeFilePath);
diff --git a/src/WingetCreateCLI/Properties/Resources.Designer.cs b/src/WingetCreateCLI/Properties/Resources.Designer.cs
index 4e7edc46..f64b9da0 100644
--- a/src/WingetCreateCLI/Properties/Resources.Designer.cs
+++ b/src/WingetCreateCLI/Properties/Resources.Designer.cs
@@ -222,6 +222,15 @@ public static string Author_KeywordDescription {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Vanity URL detected. The submission will automatically replace the previous version..
+        /// </summary>
+        public static string AutoReplacingPreviousVersion_Message {
+            get {
+                return ResourceManager.GetString("AutoReplacingPreviousVersion_Message", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to BACK.
         /// </summary>
diff --git a/src/WingetCreateCLI/Properties/Resources.resx b/src/WingetCreateCLI/Properties/Resources.resx
index b923f1fc..0631b7fe 100644
--- a/src/WingetCreateCLI/Properties/Resources.resx
+++ b/src/WingetCreateCLI/Properties/Resources.resx
@@ -1118,4 +1118,7 @@
   <data name="UseOverrides_ErrorMessage" xml:space="preserve">
     <value>Try using the architecture and/or scope overrides to uniquely match new URLs to existing installer nodes in the manifest.</value>
   </data>
+  <data name="AutoReplacingPreviousVersion_Message" xml:space="preserve">
+    <value>Vanity URL detected. The submission will automatically replace the previous version.</value>
+  </data>
 </root>
\ No newline at end of file