When I earn an achievement, is that recorded in my account or stored locally in the OctoPrint instance? I'm wondering because if I have multiple instances, do I have to earn the achievement for each installation, or will it automatically show that it is earned from another instance.
It's stored per instance.
As I suspected. Oh well. Guess I just have to print more! 
Thank you sir!
For the record, each instance of OctoPrint only ever knows about what's going on on its own instance. There's no shared account, cloud component or anything like that here, at least not as part of the core (whatever various cloud based plugins do here is out of my control). OctoPrint instance A has no knowledge of accounts, files, etc on instance B.
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Thanks for the clarification, Gina!