In that case, it’s easier. If you’re using Ubuntu, than you can crontab the certificate renewal with certbot. You only need to maintain the certificate for the web adaptors. ArcGIS magically ignores that internal services certificates.

On Ubuntu you can deploy the web adaptors on tomcat and configure it to point to the certificate you need. It can also be done with Apache but I’m less experienced with that.

Also, thanks for the tip about the disconnected environment! We’re not using AWS but still good to know!