Issuing cert seems stuck

I am attempting to issue a certificate for one of my applications and I keep seeing:

❯ flyctl certs check xxx.domain.com --config fly/production.toml
The certificate for xxx.domain.com has not been issued yet.
You are creating a certificate for xxx.domain.com
We are using Let's Encrypt for this certificate.

You can configure your DNS for xxx.domain.com by:

1: Adding an CNAME record to your DNS service which reads:

    CNAME xxx. app.fly.dev

I tried removing the cert and re-adding it but still no luck. Earlier today I issued a certificate no problems. This one was/is different because I issued the cert before I created the DNS entry but I’ve used the UI and CLI to “check” for updates but no changes so far. The DNS entry existed about 2 minutes after I created the cert for the first time.

Any help would be appreciated.