diff --git a/pkg/cmd/repo/sync/http.go b/pkg/cmd/repo/sync/http.go
index 61a1c3317..3e193daeb 100644
--- a/pkg/cmd/repo/sync/http.go
+++ b/pkg/cmd/repo/sync/http.go
@@ -32,8 +32,6 @@ func latestCommit(client *api.Client, repo ghrepo.Interface, branch string) (com
 
 type upstreamMergeErr struct{ error }
 
-var upstreamMergeUnavailableErr = upstreamMergeErr{errors.New("upstream merge API is unavailable")}
-
 var missingWorkflowScopeRE = regexp.MustCompile("refusing to allow.*without `workflow` scope")
 var missingWorkflowScopeErr = errors.New("Upstream commits contain workflow changes, which require the `workflow` scope to merge. To request it, run: gh auth refresh -s workflow")
 
@@ -60,8 +58,6 @@ func triggerUpstreamMerge(client *api.Client, repo ghrepo.Interface, branch stri
 					return "", missingWorkflowScopeErr
 				}
 				return "", upstreamMergeErr{errors.New(httpErr.Message)}
-			case http.StatusNotFound:
-				return "", upstreamMergeUnavailableErr
 			}
 		}
 		return "", err
diff --git a/pkg/cmd/repo/sync/sync.go b/pkg/cmd/repo/sync/sync.go
index 1f734b543..dd52868d1 100644
--- a/pkg/cmd/repo/sync/sync.go
+++ b/pkg/cmd/repo/sync/sync.go
@@ -284,6 +284,13 @@ func executeLocalRepoSync(srcRepo ghrepo.Interface, remote string, opts *SyncOpt
 	return nil
 }
 
+// ExecuteRemoteRepoSync will take several steps to sync the source and destination repositories.
+// First it will try to use the merge-upstream API endpoint. If this fails due to merge conflicts
+// or unknown merge issues then it will fallback to using the low level git references API endpoint.
+// The reason the fallback is necessary is to better support these error cases. The git references API
+// endpoint allows us to sync repositories that are not fast-forward merge compatible. Additionally,
+// the git references API endpoint gives more detailed error responses as to why the sync failed.
+// Unless the --force flag is specified we will not perform non-fast-forward merges.
 func executeRemoteRepoSync(client *api.Client, destRepo, srcRepo ghrepo.Interface, opts *SyncOptions) (string, error) {
 	branchName := opts.Branch
 	if branchName == "" {
@@ -317,8 +324,9 @@ func executeRemoteRepoSync(client *api.Client, destRepo, srcRepo ghrepo.Interfac
 		return "", err
 	}
 
-	// This is not a great way to detect the error returned by the API
-	// Unfortunately API returns 422 for multiple reasons
+	// Using string comparison is a brittle way to determine the error returned by the API
+	// endpoint but unfortunately the API returns 422 for many reasons so we must
+	// interpret the message provide better error messaging for our users.
 	err = syncFork(client, destRepo, branchName, commit.Object.SHA, opts.Force)
 	var httpErr api.HTTPError
 	if err != nil {
diff --git a/pkg/cmd/repo/sync/sync_test.go b/pkg/cmd/repo/sync/sync_test.go
index a532f3992..eafc0835e 100644
--- a/pkg/cmd/repo/sync/sync_test.go
+++ b/pkg/cmd/repo/sync/sync_test.go
@@ -292,7 +292,7 @@ func Test_SyncRun(t *testing.T) {
 					httpmock.StringResponse(`{"data":{"repository":{"defaultBranchRef":{"name": "trunk"}}}}`))
 				reg.Register(
 					httpmock.REST("POST", "repos/FORKOWNER/REPO-FORK/merge-upstream"),
-					httpmock.StatusStringResponse(404, `{}`))
+					httpmock.StatusStringResponse(422, `{}`))
 				reg.Register(
 					httpmock.REST("GET", "repos/OWNER/REPO/git/refs/heads/trunk"),
 					httpmock.StringResponse(`{"object":{"sha":"0xDEADBEEF"}}`))