So as a followup to my previous post, I realized that I have been using Cloudflare as my DNS provider (i.e. the IP address for my server is specified on Cloudflare).
As far as I can tell I therefore need to specify the -le and --dns="dns_cf flags to obtain the necessary letsencrypt certificate for my site. So I ran the following command:
wo site update examplesite.com -le --dns=dns_cf
and obtained the following output:
Certificate type : domain
Validation mode : DNS mode with dns_cf
Issuing SSL cert with acme.sh [OK]
Deploying SSL cert [OK]
Securing WordOps backend with current cert
Adding HTTPS redirection [OK]
Updating site url with https [OK]
Testing Nginx configuration [OK]
Reloading Nginx [OK]
Congratulations! Successfully Configured SSL on https://wildcatwellness.org
Your cert will expire within 89 days.
Cloudflare shows my SSL/TLS encryption mode as "flexible" however I still get an ERROR 522 - Connection Timed Out error when I try to access my site using https://www.examplesite.com/wp-admin.
Can anyone help?