diff --git a/src/WingetCreateCLI/Commands/BaseCommand.cs b/src/WingetCreateCLI/Commands/BaseCommand.cs
index 6dc9b2aa..1e547cac 100644
--- a/src/WingetCreateCLI/Commands/BaseCommand.cs
+++ b/src/WingetCreateCLI/Commands/BaseCommand.cs
@@ -503,9 +503,11 @@ protected async Task<bool> GitHubSubmitManifests(Manifests manifests)
                     Logger.ErrorLocalized(nameof(Resources.Error_Prefix), e.Message);
                     return false;
                 }
-                else if (e is NonFastForwardException nonFastForwardException)
+                else if (e is Octokit.NotFoundException)
                 {
-                    Logger.ErrorLocalized(nameof(Resources.FastForwardUpdateFailed_Message), nonFastForwardException.CommitsAheadBy);
+                    // This exception can occur if the client is unable to create a reference due to being behind by too many commits.
+                    // The user will need to manually update their master branch of their winget-pkgs fork.
+                    Logger.ErrorLocalized(nameof(Resources.SyncForkWithUpstream_Message));
                     return false;
                 }
                 else
diff --git a/src/WingetCreateCLI/Properties/Resources.Designer.cs b/src/WingetCreateCLI/Properties/Resources.Designer.cs
index facb9e64..48315012 100644
--- a/src/WingetCreateCLI/Properties/Resources.Designer.cs
+++ b/src/WingetCreateCLI/Properties/Resources.Designer.cs
@@ -744,15 +744,6 @@ public static string ExternalDependencies_KeywordDescription {
             }
         }
         
-        /// <summary>
-        ///   Looks up a localized string similar to Failed to update fork because the default branch is ahead by {0} commit(s). .
-        /// </summary>
-        public static string FastForwardUpdateFailed_Message {
-            get {
-                return ResourceManager.GetString("FastForwardUpdateFailed_Message", resourceCulture);
-            }
-        }
-        
         /// <summary>
         ///   Looks up a localized string similar to [{0}] value is.
         /// </summary>
@@ -2031,6 +2022,15 @@ public static string Switches_KeywordDescription {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Unable to create a reference to the forked repository. This can be caused when the forked repository is behind by too many commits. Sync your fork and try again..
+        /// </summary>
+        public static string SyncForkWithUpstream_Message {
+            get {
+                return ResourceManager.GetString("SyncForkWithUpstream_Message", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to List of additional package search terms.
         /// </summary>
diff --git a/src/WingetCreateCLI/Properties/Resources.resx b/src/WingetCreateCLI/Properties/Resources.resx
index 9543ca13..dc1ae034 100644
--- a/src/WingetCreateCLI/Properties/Resources.resx
+++ b/src/WingetCreateCLI/Properties/Resources.resx
@@ -890,10 +890,6 @@
   <data name="UpgradeCode_KeywordDescription" xml:space="preserve">
     <value>UpgradeCode used for correlation of packages across sources</value>
   </data>
-  <data name="FastForwardUpdateFailed_Message" xml:space="preserve">
-    <value>Failed to update fork because the default branch is ahead by {0} commit(s). </value>
-    <comment>{0} - represents the number of commits the default branch is ahead by</comment>
-  </data>
   <data name="DisplayInstallWarnings_KeywordDescription" xml:space="preserve">
     <value>Indicates whether winget should display a warning message if the install or upgrade is known to interfere with running applications</value>
   </data>
@@ -919,4 +915,7 @@
     <value>List of winget arguments the installer does not support</value>
     <comment>"winget" is the proper name of the tool</comment>
   </data>
+  <data name="SyncForkWithUpstream_Message" xml:space="preserve">
+    <value>Unable to create a reference to the forked repository. This can be caused when the forked repository is behind by too many commits. Sync your fork and try again.</value>
+  </data>
 </root>
\ No newline at end of file
diff --git a/src/WingetCreateCore/Common/GitHub.cs b/src/WingetCreateCore/Common/GitHub.cs
index 5cadb25c..d2c229fd 100644
--- a/src/WingetCreateCore/Common/GitHub.cs
+++ b/src/WingetCreateCore/Common/GitHub.cs
@@ -307,22 +307,30 @@ private async Task<PullRequest> SubmitPRAsync(string packageId, string version,
             var upstreamMasterSha = upstreamMaster.Object.Sha;
 
             Reference newBranch = null;
+            bool forkSyncAttempted = false;
 
             try
             {
-                var retryPolicy = Policy.Handle<ApiException>().WaitAndRetryAsync(3, i => TimeSpan.FromSeconds(i));
+                var retryPolicy = Policy
+                    .Handle<ApiException>()
+                    .Or<NonFastForwardException>()
+                    .WaitAndRetryAsync(3, i => TimeSpan.FromSeconds(i));
+
                 await retryPolicy.ExecuteAsync(async () =>
                 {
-                    try
+                    // Related issue: https://github.com/microsoft/winget-create/issues/282
+                    // There is a known issue where a reference is unable to be created if the fork is behind by too many commits.
+                    // Always attempt to sync fork during first execution in order to mitigate the possibility of this scenario occurring.
+                    // If the fork is behind by too many commits, syncing will also fail with a NotFoundException.
+                    // Updating the fork can fail if it is a non-fast forward update, but this should not be blocking as pull request submission can still proceed.
+                    // If creating a reference fails, that means syncing the fork also failed, therefore the user will need to manually sync their repo regardless.
+                    if (!forkSyncAttempted && submitToFork)
                     {
-                        await this.github.Git.Reference.Create(repo.Id, new NewReference($"refs/{newBranchNameHeads}", upstreamMasterSha));
-                    }
-                    catch (Octokit.NotFoundException)
-                    {
-                        // Creating a reference can sometimes fail with a NotFoundException if the fork is not up to date with the upstream repository.
+                        forkSyncAttempted = true;
                         await this.UpdateForkedRepoWithUpstreamCommits(repo);
-                        throw;
                     }
+
+                    await this.github.Git.Reference.Create(repo.Id, new NewReference($"refs/{newBranchNameHeads}", upstreamMasterSha));
                 });
 
                 // Update from upstream branch master