How often should you test your backup generator?

Grumpty's answer
Every month
Why bother
An untested generator won't start in the outage. Standard upkeep. Dull and cheap, and a lot less dull than whatever it's quietly preventing.
When to start thinking about it
No notice needed, really. Grumpty mentions it the day it comes due and that's that. Mark it done and Grumpty sets the next one, every month, so you can go back to forgetting it exists.
Let Grumpty remember it for you
Add it once. Grumpty tracks the date, grumbles when it's due, and rolls it forward the moment you mark it done. No spreadsheets, no sticky notes, no forgetting.
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