At my previous employer, we were running self-hosted Airflow in AWS, which really was a nightmare. The engineer that set it up didn't account for any kind of scaling and all the code was a mess. We would also get issues like logs not syncing correctly in our environment or transient networking issues that somehow didn't fail the given Airflow task. Eventually, we did a dual migration: temporarily switching to AWS managed Airflow (their Amazon Managed Workflows for Apache Airflow product) while also rewriting the DAGs in Dagster.

Dagster was a great solution for us. Their notion of software defined assets allowed us to track metadata of the Redshift and Snowflake tables we were working with. Working with re-runs and partitioned data was a breeze. It did take a while to onboard the whole team and get things working smoothly, which was a bit difficult because Dagster is still young and they were often making changes to how parts of the system worked (although nothing that was immediately backwards incompatible).

We also enjoyed some of the out of the box features like resources and unit testing jobs. Overall, I think it made our team focus more on our data and what we wanted to do with it rather than feeling like we had to wrangle with Airflow just to get things running.