Since upgrading to version 4.1 applying retention policies fails on every run.
I have since installed 4.2, however I just noticed the failures in the task log and they started ~ 30 minutes after I downloaded & installed the 4.1 update (going by the installer create date/time).
Sorry about the experience on this one, you’ve run into this issue. We have a fix ready to go and it should ship in Octopus 2019.4.3 which is due to go out today (so in the next few hours).
Please let me know if there is anything else that I can help with.
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