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

This worked for me:

 brew install openssl
 cd /usr/local/include 
 ln -s ../opt/openssl/include/openssl .

Answer 2

Note: this no longer works due to https://github.com/Homebrew/brew/pull/612

I had the same problem today. I uninstalled (unbrewed??) openssl 1.0.2 and installed 1.0.1 also with homebrew. Dotnet new/restore/run then worked fine.

Install openssl 101:
brew install homebrew/versions/openssl101
Linking:
brew link --force homebrew/versions/openssl101

Answer 3

This is what worked for me:

brew update
brew install openssl
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/
ln -s /usr/local/Cellar/openssl/1.0.2j/bin/openssl /usr/local/bin/openssl

Thanks to @dorlandode on this thread https://github.com/Homebrew/brew/pull/597

NB: I only used this as a temporary fix until I could spend time correctly installing Openssl again from scratch. As I remember I spent best part of a day debugging and having issues before I realised the best way was to manually install the certs I needed one by one. Please read the link in @bouke's comment before attempting this.

Answer 4

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.

Answer 5

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

Answer 6

After trying everything I could find and nothing worked, I just tried this:

touch ~/.bash_profile; open ~/.bash_profile

Inside the file added this line.

export PATH="$PATH:/usr/local/Cellar/openssl/1.0.2j/bin/openssl"

now it works :)

Jorns-iMac:~ jorn$ openssl version -a
OpenSSL 1.0.2j  26 Sep 2016
built on: reproducible build, date unspecified
//blah blah
OPENSSLDIR: "/usr/local/etc/openssl"

Jorns-iMac:~ jorn$ which openssl
/usr/local/opt/openssl/bin/openssl