Homebrew refusing to link OpenSSL

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've upgraded/installed the latest version of openssl:

> brew install openssl
==> Downloading https://homebrew.bintray.com/bottles/openssl-1.0.2h_1.el_capitan.bottle.tar.gz
Already downloaded: /Users/administrator/Library/Caches/Homebrew/openssl-1.0.2h_1.el_capitan.bottle.tar.gz
==> Pouring openssl-1.0.2h_1.el_capitan.bottle.tar.gz
==> Caveats
A CA file has been bootstrapped using certificates from the system
keychain. To add additional certificates, place .pem files in
  /usr/local/etc/openssl/certs

and run
  /usr/local/opt/openssl/bin/c_rehash

This formula is keg-only, which means it was not symlinked into /usr/local.

Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries

Generally there are no consequences of this for you. If you build your
own software and it requires this formula, you'll need to add to your
build variables:

    LDFLAGS:  -L/usr/local/opt/openssl/lib
    CPPFLAGS: -I/usr/local/opt/openssl/include

But when I try to link openssl I continue to run into this linking error:

> brew link --force openssl
Warning: Refusing to link: openssl
Linking keg-only OpenSSL means you may end up linking against the insecure,
deprecated system version while using the headers from the Homebrew version.
Instead, pass the full include/library paths to your compiler e.g.:
  -I/usr/local/opt/openssl/include -L/usr/local/opt/openssl/lib

The option to include compiler flags doesn't make sense to me, since I'm not compiling these libraries that I'm dependent on.

EDIT dotnetcore has updated their instructions:

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/

Solution 1:

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.

Solution 2:

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).

Solution 3:

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