As far as I know, (and tested) Ruby versions < 2.4 requires libssl1.0, while >2.4 libssl1.1+. The two libssl packages conflict with each other, so you can't have both of them, so I had to juggle the libs in order to install the required ruby version. To make things even funnier (or more complicated), Ruby <2.4 tends to require gcc-6 instead of the current upstream version (which is 7). So, usually it looks like that:
for ruby <2.4
apt install libssl1.0-dev
rbenv install `version`for ruby >2.4
apt install libssl-dev
rbenv install `version`
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