Homebrew refusing to link OpenSSL

Question

I\'m on: OSX 10.11.6, Homebrew version 0.9.9m OpenSSL 0.9.8zg 14 July 2015

I\'m trying to play with with dotnetcore and by following their instructions,

I\'

Answer 1

The solution might be updating some tools.

Here's my scenario from 2020 with Ruby and Python:

I needed to install Python 3 on Mac and things escalated. In the end, updating homebrew, node and python lead to the problem with openssl. I did not have openssl 1.0 anymore, so I couldn't "brew switch" to it.
So what was still trying to use that old 1.0 version?

It tuned out it was Ruby 2.5.5.
So I just installed Ruby 2.5.8 and removed the old one.

Other things you can try if this is not enough: Use rbenv and pyenv. Clean up gems and formulas. Update homebrew, node, yarn. Upgrade bundler. Make sure your .bash_profile (or equivalent) is set up according to each tool's instructions. Reopen the terminal.