Openssl, Rvm, Brew, Conflicting Error

macOS 10.12 brew install openssl issue

I managed to resolve it by editing formula (brew edit openssl)
and adding

-I/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk/usr/include

to args array in configure_args.

As below:

  def configure_args
    args = %W[
      --prefix=#{prefix}
      --openssldir=#{openssldir}
      no-ssl3
      no-ssl3-method
      no-zlib
      ##### add the line here ####
      -I/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk/usr/include
    ]
    on_linux do
      args += (ENV.cflags || "").split
      args += (ENV.cppflags || "").split
      args += (ENV.ldflags || "").split
      args << "enable-md2"
    end
    args
  end

Brew update breaks openssl

Thanks to help from the discourse page on brew.sh I was able to find the cause of my problem.

The automatic update of brew and its formulas had overwritten not only the symlink for openssl@1.1 but also the generic openssl link in /usr/local/opt. Both pointed now to /usr/local/Cellar/openssl@1.1, whereas on my second dev system the openssl symlink pointed still to /usr/local/Cellar/openssl.

After I recreated the openssl symlink for /usr/local/Cellar/openssl everything works again.

The context is that openssl 1.1 is the safest version whereas 1.0 has been deprecated to my knowledge. But in my case it is only to maintain a legacy project in development.

Now I will have one more thing to do after every brew update/upgrade: verify symlinks, after the recent introduction of auto purging of old versions already forces me to copy them back into my system from a backup.

Make error - Installing RVM on Snow Leopard

Try installing with --with-openssl-dir=/path/to/openssl with the location of your installed openssl version.

more over you can look at this https://rvm.io/packages/openssl/

Installing Rails on Mac OS fails with several errors

Run this command first

sudo chown -R <your username>:admin /usr/local

Replace <your username> with whatever your username on your mac is. So, in my case, I would run

sudo chown -R Adrian:admin /usr/local

Then try installing rbenv and ruby-build.

Your problem is most likely caused by the use of package installers (.pkg files) as they tend to create files as root in places where they shouldn't.

Note: you can find out your username by running whoami

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