Homebrew refusing to link OpenSSL

Question

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.

As the update to the other answer suggests, the workaround of installing the old openssl101 brew will no longer work. For a right-now workaround, see this comment on dotnet/cli#3964.

The most relevant part of the issue copied here:

I looked into the other option that was suggested for setting the rpath on the library. I think the following is a better solution that will only effect this specific library.

sudo install_name_tool -add_rpath /usr/local/opt/openssl/lib /usr/local/share/dotnet/shared/Microsoft.NETCore.App/1.0.0/System.Security.Cryptography.Native.dylib

and/or if you have NETCore 1.0.1 installed perform the same command for 1.0.1 as well:

sudo install_name_tool -add_rpath /usr/local/opt/openssl/lib /usr/local/share/dotnet/shared/Microsoft.NETCore.App/1.0.1/System.Security.Cryptography.Native.dylib

In effect, rather than telling the operating system to always use the homebrew version of SSL and potentially causing something to break, we're telling dotnet how to find the correct library.

Also importantly, it looks like Microsoft are aware of the issue and and have both a) a somewhat immediate plan to mitigate as well as b) a long-term solution (probaby bundling OpenSSL with dotnet).

Another thing to note: /usr/local/opt/openssl/lib is where the brew is linked by default:

13:22 $ ls -l /usr/local/opt/openssl
lrwxr-xr-x  1 ben  admin  26 May 15 14:22 /usr/local/opt/openssl -> ../Cellar/openssl/1.0.2h_1

If for whatever reason you install the brew and link it in a different location, then that path is the one you should use as an rpath.

Once you've update the rpath of the System.Security.Cryptography.Native.dylib libray, you'll need to restart your interactive session (i.e., close your console and start another one).

None of these solutions worked for me on OS X El Capitan 10.11.6. Probably because OS X has a native version of openssl that it believes is superior, and as such, does not like tampering.

So, I took the high road and started fresh...

---

Manually install and symlink

cd /usr/local/src  

• If you're getting "No such file or directory", make it:

  cd /usr/local && mkdir src && cd src

Download openssl:

curl --remote-name https://www.openssl.org/source/openssl-1.0.2h.tar.gz

Extract and cd in:

tar -xzvf openssl-1.0.2h.tar.gz
cd openssl-1.0.2h

Compile and install:

./configure darwin64-x86_64-cc --prefix=/usr/local/openssl-1.0.2h shared
make depend
make
make install

Now symlink OS X's openssl to your new and updated openssl:

ln -s /usr/local/openssl-1.0.2h/bin/openssl /usr/local/bin/openssl

Close terminal, open a new session, and verify OS X is using your new openssl:

openssl version -a

Just execute brew info openssland read the information where it says:

If you need to have this software first in your PATH run: echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile

If migrating your mac breaks homebrew:

I migrated my mac, and it unlinked all my homebrew installs - including OpenSSL. This broke gem install, which is how I first noticed the problem and started trying to repair this.

After a million solutions (when migrating to OSX Sierra - 10.12.5), the solution ended up being comically simple:

brew reinstall ruby
brew reinstall openssl

Edit much later: as Gal Bracha noted in the comments, you ?might? need to delete /usr/local/opt/openssl before doing the reinstalls, just to be safe. I didn't need to at the time, but if you're still having trouble, give that a try.

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