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The available software to do the automatic 90 day cert renewals don't work on anything but the latest operating systems. Go back a handful of years and they just crap out.

Certbot supports Ubuntu 12.04+ (14.04+ for the apache plugin), CentOS/RHEL 6+, and Debian 7+. With the exception of CentOS/RHEL 5 (which was released in 2007!), all releases of those distributions that still receive security updates are supported.

What OS are you referring to?

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