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I've gone through their automatic setup and followed the youtube tutorial from Lawrence Systems. I entered all the required information for the setup correctly (apart from the email maybe). The tutor got his dashboard page hosted with https properly enabled with no additional configuration and I expected mine to work the same. I've tried to regenerate the certificates according to the official docs, but I still get the same result. I honestly don't know where else the problem could've arised. As much as I hate it, I think I'll have to go through the logs after all.
Selfhosting without checking the logs to hunt down errors? That's not going to be pretty.
The mail address is not the issue. You can enter any address you want there if you don't care about Let's Encrypt being able to reach you in case of problems (they won't).
Don't be afraid of the logs. You don't have to read or understand every line of them. You have an issue with your certificate? Search for certificate and read the lines above and below to get clues what might have gone wrong.
Thank you for your assist. I found the underlying issue to be with the DNS from the domain provider. I switched to Cloudflare DNS and now it works flawlessly.
for future reference there are a few ports that need to be open for let's encrypt to work, and it has a very small timeout (as you have found) so if the dns isn't great it fails. Cloudflare will cache your site/dns so usually works
Its just port 80. And letsencrypt provides a CIDR block so us paranoids who still restrict with firewalls can limit the exposure.