How can I configure it to send an email to the administrator when a new version is available for update? Instead of the administrator logging in to the background to check if there are updates?
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I don’t seem to have received any similar emails. Do I need to configure it somewhere?
The setting should be enabled by default.
What could be the case here is that You’re checking for updates in /admin/upgrade too frequently.
Discourse will only send an email when there is a new “release” is available but updates are available in docker manager whenever a commit hits the tests-passed branch.
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Well, yes, but it still might be worth a check to see if it’s been accidentally disabled. 
Also, it’s for the contact_email address, and isn’t configurable to send to a different/specific admin. But hopefully the contact email is still monitored. 
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5 posts were split to a new topic: Change sending New Version email to developer email (or configurable group)