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\'
I had the same problem while trying to install newer version of ruby 2.6.5 https://github.com/kelaberetiv/TagUI/issues/86 helps me to solve the problem. This if for macOS catalina Version 10.15.1
Basically, I did update and upgrade
homebrew and install openssl and install ruby.
brew update && brew upgrade
brew install openssl
Then create these 2 symlinks
ln -s /usr/local/opt/openssl/lib/libcrypto.1.0.0.dylib /usr/local/lib/
ln -s /usr/local/opt/openssl/lib/libssl.1.0.0.dylib /usr/local/lib/
then installed ruby 2.6.5