Proxied vs DNS only: only loads when DNS only is set

You need a valid certificate on your server, it does not necessarily have to be an Origin certificate. It has to cover all required hostnames, however, and your current certificate does not, hence it cannot work. You need to make sure it does.

As mentioned, pause Cloudflare and make sure it actually loads fine on HTTPS. Then it won’t be an issue on Cloudflare either.

I do have an Origin Certificate from cloudflare. Do I need another as well? Is there a way to get a certificate that covers all *.prkr.computer or do I need a different one for each subdomain?

I have paused cloudflare, and checked that it loads on HTTPS. It does not, I’m trying to figure out why/how to fix it.

There currently is no Origin certificate. And yes, what you described is a regular wildcard certificate.

Keep Cloudflare paused until it loads fine on HTTPS. Only exception, should you be using an Origin certificate, you’ll still get a warning because it’s not trusted by browsers, but that’s not an issue for the proxies. However, the certificate still needs to cover all hostnames (also as part of a wildcard).

Shows there being an origin certificate?

You may have issued a certificate, but that certificate is not configured with your server.

Thank you for the help! I had installed some letsencrypt certificates on the server and had not installed the certificate from cloudflare.

That was the issue. Thanks so much for your patient help!

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