You'd need a plugin that reacts to a URL request, so probably component plugin, and checks the database for those not logged in recently then sends an email to them. You'd need to secure it with some sort of unique code added to the URL that only you know. You'd then need to setup CRON to that URL every few days or so.
The alternative is a plugin that fires after a user logs in that checks for users who haven't logged in recently and sends out emails, but this isn't exactly as reliable or performance safe as the CRON usage. This would only fire if someone logged in to trigger it and it'd fire on every login unless you implemented some sort of timer feature so it only happens once a day, etc..
Either way it's going to take custom development.
Kyle (Krileon)
Community Builder Team Member
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krileon
