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Do note that I'm not sponsored by Directadmin (Hi John and crew) nor by Let's Encrypt. You need to login once via SSH to update Directadmin and enable Let's Encrypt.
I just like them a lot both, Directadmin for being a lightweight but very easy and functional controlpanel, and Let's Encrypt for their effort to secure the entire web for free. You can update Directadmin via the Administrator Settings - Update / Licensing page as well, but I like the custombuild method better. Because you can update the other parts of your server as well and that a general good thing to do.
They make it a breeze to set up TLS certificates for your web server. Let's Encrypt is supported by major players like Mozilla, Akamai, Cisco, the EFF, the Internet Security Research Group and others.
Let's Encrypt provides free, automatic and secure certificates so that every website can be secured with an SSL certificate.
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Also, you do need to login via SSH and execute a few other steps like enabling Let's Encrypt and rewriting the configuration files, so you might just as well login and update via Custombuild.
Direct Admin now supports Lets Encrypt natively since version 1.50, so no more ssh fiddling, just via the control panel, for all the users on the server.You can test with a subdomain as well, but make sure to add the subdomain as a new domain, not as a subdomain (So, Domain Administration, Add a domain, testsub.example.org).Actual subdomains don't support seperate SSL in Directadmin.Of course, you can, but it will take too much time to set everything up. Let's Encrypt is a new certificate authority, recognized by all major browsers.