I’m new to Dagster, but concepts and terminology are similar to others tools, mainly Airflow. You may want to read about
sensors, which may or may not work similarly--I have no direct experience with them in Dagster. There are still open questions about your architecture, such as whether or not the remote service can call back, etc. If it could you could not “retry or check regularly” and instead let it simply trigger a new job asynchronously. Again, just thinking out loud, but sensors would be the first thing I’d look into.