Homebrew refusing to link OpenSSL


Question or issue on macOS:

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

and run

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/

How to solve this problem?

Solution no. 1:

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 no. 2:

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 no. 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 

Solution no. 4:

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

Solution no. 5:

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

Solution no. 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

Solution no. 7:

I have a similar case. I need to install openssl via brew and then use pip to install mitmproxy. I get the same complaint from brew link --force. Following is the solution I reached: (without force link by brew)

pip install mitmproxy

This does not address the question straightforwardly. I leave the one-liner in case anyone uses pip and requires the openssl lib.

Note: the /usr/local/opt/openssl/lib paths are obtained by brew info openssl

Solution no. 8:

This worked for me:

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

Solution no. 9:

The solution above from edwardthesecond worked for me too on Sierra

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

Other steps I did before were:

  • installing openssl via brew

    brew install openssl 
  • adding openssl to the path as suggested by homebrew

    brew info openssl echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile 

Solution no. 10:

By default, homebrew gave me OpenSSL version 1.1 and I was looking for version 1.0 instead. This worked for me.

To install version 1.0:

brew install https://github.com/tebelorg/Tump/releases/download/v1.0.0/openssl.rb

Then I tried to symlink my way through it but it gave me the following error:

ln -s /usr/local/Cellar/openssl/1.0.2t/include/openssl /usr/bin/openssl
ln: /usr/bin/openssl: Operation not permitted

Finally linked openssl to point to 1.0 version using brew switch command:

brew switch openssl 1.0.2t
Cleaning /usr/local/Cellar/openssl/1.0.2t
Opt link created for /usr/local/Cellar/openssl/1.0.2t

Hope this helps!