Trouble with SSL after lots of rebuilds

[Remah (Just another happy Discourse user)]

@Queth

Does it request a LE certificate at each rebuild?

No. AFAIK, it checks the renewal date and renews when needed.

Apparently you can get five certificates in seven days:

Cloudflare with Discourse

There’s no reason you’d need a different IP. There may be other problems, but this will be a definite blocker. …which is your problem. Let’s Encrypt will only issue five certs for a given set of FQDNs within a week. You exhausted that limit within 45 minutes. Once you did that, any further attempt at installation was guaranteed to fail.