I was just trying to delete outright, haven’t seen any duplicate issues.

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It's most likely a relay issue, deletion requests I've tested are all working and I haven't made changes to the deletion code recently. What relays are you connected to in settings?

Yeah, those are the defaults. With the sendit relay it should be publishing the deletion requests properly, so it might actually be a caching issue. I'll look into it a bit more this weekend.