There is trouble brewing, or: Openssl issues on Ruby with Homebrew

This post is to describe an issue I’ve run into using < 2.3 versions of Ruby on OSX with rvm and brew.

Don’t even get me started on working with older versions of Ruby — we have some maintenance projects running in ruby-1.8.3! Even modern Rubies may give you a hard time, however, and this is one of the times. Actually, I am writing this post as a reminder for me because I ran into the same problem twice now, and what is worse, the second time it took me nearly the same amount of fruitless googling to solve it as it took the first. And the solution was the same! So, let us proceed with order.

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