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Yes mixed segment granularity like this should work. What are your early/late message rejection settings for your ingestion tasks? Can you check to see if you are actively ingesting data and creating segments in all of these time chunks, and that your compaction job isn't colliding with one of them? Also, what version of Druid are you on?

25.0.0. I don't have any early / late rejection settings at the moment, as I'm still just testing things out. The time chunk that was errant was 2023-02-21, so basically, the current day. When I changed the ingestion to 'month' suddenly it started working. But I had marked as unused and then killed everything from 2023-02-01 on, and double checked there was nothing stray in s3 for that time range. Is it possible the coordinator thought it knew something it didn't and I should have restarted it?

Ingesting into time chunks where there is already an existing segment with partially or fully overlapping that time chunk, shouldn't matter ... the ingestion just starts a new segment in the time chunk you specified, and later on you compact them together. If your issue was that ingestion was not working, unfortunately I don't know enough about process communications here to be of much help. If you changed ingestion segment granularity though that means you must have restarted the supervisor, so that could have reset something and hte change in granularity not needed.

Okay well I'll experiment with it some more. I'm sure it is something simple, I just wish the error message it gave back was more explicit.