My web server is (include version): Apache/2.4.10 (Raspbian) and Python 2.7.9
The operating system my web server runs on is (include version): Debian (raspbian) Jessie
I can login to a root shell on my machine (yes or no, or I don’t know): yes
I have previously used CERTBOT on another Debian (Raspbian) Jessie system without any issues, This is a newly created system and I was following the commands at https://certbot.eff.org/#debianjessie-apache
xxx@goosegate:~ $ certbot --apache
I went through a lot of debugging with the other user but I originally didn't realize what @Patches ended up telling us, which was that there are two versions of the ARM architecture that Raspbian doesn't distinguish between properly. Thus, it's willing to install library packages that aren't applicable to the actual ARM hardware that you have on your Pi. That leads to these illegal instruction errors.
I'm not sure that I understood in the other thread what people are recommended to do about this situation.
@philpugh You are using a Raspberry Pi 1, not the later models, correct? Debian Backports isn’t compatible with the ARMv6 processor used in the Raspberry Pi 1 and this leads to illegal instruction errors. (Officially, it isn’t compatible with the later versions either, because it is built against Debian proper and not the Raspbian rebuild, but it typically works fine.)
You could use certbot-auto, which has no dependencies on backports for Jessie and should be fine. You must remove all packages you installed from backports first, however, as even one dependency would get picked up and cause crashes.
Or you could upgrade to Raspbian Stretch, where certbot is included in the release and would be built properly for the Pi 1.