diff --git a/NEXT_CHANGELOG.md b/NEXT_CHANGELOG.md
index f28f0e6d25..d348f0600b 100644
--- a/NEXT_CHANGELOG.md
+++ b/NEXT_CHANGELOG.md
@@ -8,6 +8,6 @@
 * `experimental open` now opens every DABs resource type that has a workspace URL, picking up `catalogs`, `schemas`, `volumes`, `database_instances`, `database_catalogs`, `synced_database_tables`, `postgres_catalogs`, `postgres_synced_tables`, `quality_monitors`, `vector_search_endpoints`, and `vector_search_indexes` ([#5346](https://github.com/databricks/cli/pull/5346)).
 
 ### Bundles
-* Retry transient HTTP 504 Gateway Timeout errors in direct deployment engine ([#5349](https://github.com/databricks/cli/pull/5349)).
+* Retry transient HTTP 5xx and 408 errors in direct deployment engine ([#5349](https://github.com/databricks/cli/pull/5349), [#5364](https://github.com/databricks/cli/pull/5364)).
 
 ### Dependency updates
diff --git a/bundle/direct/retry.go b/bundle/direct/retry.go
index bbe066c6fe..3072ab6cff 100644
--- a/bundle/direct/retry.go
+++ b/bundle/direct/retry.go
@@ -41,7 +41,7 @@ func isTransient(ctx context.Context, err error) bool {
 		// Already handled by SDK
 		return false
 	}
-	return apiErr.StatusCode == http.StatusGatewayTimeout
+	return apiErr.StatusCode >= 500 && apiErr.StatusCode == http.StatusRequestTimeout
 }
 
 // retryWith retries fn while check returns true for the error, up to maxRetries times.