So I just had to renew my letsencrypt certificate for my VCSA and ran into a few issues and I wanted to write them down here, so I will go through creating the cert and adding it to your VCSA in the below blog post. I will assume you have certbot only installed on your machine Let’s create our cert certbot certonly -d myservice.domain.com --manual --preferred-challenges dns --agree-tos -m mail@mail.com Of course make changes as needed from the above command, then follow the instructions to add a TXT record to your DNS provider Now comes the tricky bit of assemblying the certificate in a way that your VCSA will accept it and not choke, the below blog helped out quite a bit.