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Tell people about the new requirements for custom user signatures
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Event Timeline

Quick update: The software change has been "live" for about two weeks, and the plain-fancy-sig error at enwiki (the wiki with the most errors) has declined from 1000+ to ~850 since then. Since our lists are only people who have made an edit during the preceding 30 days, I think this is largely new editors rolling through the system. I'm therefore going to postpone individual messages until the software has been in place for a minimum of 30 days, so that we can minimize the number of messages being sent (and therefore reduce the risk of flooding anyone's watchlist).

Update: I asked @AntiCompositeNumber to extend the timeframe in We're working with a rolling period of 90 days, which meant 1,618 editors with plain-fancy-sig late last week. I've sent directions to all of those people. We're hoping to find out what kind of response rate we get from MassMessages before trying to replicate that process at other wikis.