Updating ruby os x
The openssl extension of Ruby version before 2.4 is not compatible with Open SSL 1.1.x.
At the moment, most Linux distributions that come with Open SSL 1.1.0 have a separate package for Open SSL 1.0.x.
I provide instructions for compiling Ruby 1.9 for rbenv here. I have used this technique with easy success on Snow Leopard, Lion, and Mountain Lion.
Dan Benjamin’s Hivelogic article Installing Ruby, Ruby Gems, and Rails on Snow Leopard is the recommended place to go although the article is for 1.8, so here’s a Ruby 1.9-specific install on Snow Leopard. either go all 64-bit ‘fat’ (as is – for example – Apache on OS X, which can cause problems with 32-bit libraries) or check any gems you’re likely to use to make sure they’re okay for 64-bit.
On Debian 9 (stretch), it is Ruby 1.8.7 patchlevel 302 (and below, possibly above, including ruby enterprise edition) have a known compiler bug, however compiling Ruby will finish without errors.
The bug will cause a segmentation fault whenever an SSL connection is opened, like .../timeout.rb:60: [BUG] Segmentation fault.
Try setting the following flags and recompiling Ruby: If you can, try upgrading to Ruby 2.1.2 where this issue seems to be fixed.
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By Christopher Haupt The following instructions for installing Ruby have been tested on Mac OS X Yosemite (10.10.4).
It displays a warning about using sudo and then asks you for your password to finish the installation.