DNS Lookup of A and AAAA Records on DigitalOcean Failed

Sounds curious. If you have (or not have) DNSSEC, that has nothing to do with Letsencrypt.

But if you use DNSSEC, there are two things: The DS in the parent zone and your own valid DNSSEC-configuration (DNSKEY and signed answers). And if that doesn't work, then it's critical lto create a Letsencrypt certificate.

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