Drawpile
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Reminding for update (in chat) at interval
This feature is pretty self-explanatory. Once every 3 hours, a new system chat message will appear to notify the user if their client is out of date. This message will only be visible to the out-of-date user, and should include a link to the Drawpile website or GH releases.
The previous idea was to have a pop-up, but that may be too annoying.
Here's another possibility that would probably annoy more than a muted chat message.