macOS 10.12 brew install openssl issue

Question

Trying to install openssl on homebrew using:

brew install openssl

Is giving the following error during make:

clang  -I. -Iinclude -fPIC -arch x86_64 -O3 -Wall -DL_ENDIAN -DOPENSSL_PIC -DOPENSSL_CPUID_OBJ -DOPENSSL_IA32_SSE2 -DOPENSSL_BN_ASM_MONT -DOPENSSL_BN_ASM_MONT5 -DOPENSSL_BN_ASM_GF2m -DSHA1_ASM -DSHA256_ASM -DSHA512_ASM -DKECCAK1600_ASM -DRC4_ASM -DMD5_ASM -DAESNI_ASM -DVPAES_ASM -DGHASH_ASM -DECP_NISTZ256_ASM -DX25519_ASM -DPOLY1305_ASM -DOPENSSLDIR="\"/usr/local/etc/[email protected]\"" -DENGINESDIR="\"/usr/local/Cellar/[email protected]/1.1.1l/lib/engines-1.1\"" -D_REENTRANT -DNDEBUG  -MMD -MF crypto/rand/randfile.d.tmp -MT crypto/rand/randfile.o -c -o crypto/rand/randfile.o crypto/rand/randfile.c
In file included from crypto/rand/rand_unix.c:38:
/usr/include/CommonCrypto/CommonRandom.h:35:9: error: unknown type name 'CCCryptorStatus'
typedef CCCryptorStatus CCRNGStatus;
        ^
crypto/rand/rand_unix.c:385:47: error: use of undeclared identifier 'kCCSuccess'
    if (CCRandomGenerateBytes(buf, buflen) == kCCSuccess)
                                              ^
2 errors generated.
make[1]: *** [crypto/rand/rand_unix.o] Error 1
make[1]: *** Waiting for unfinished jobs....
make: *** [all] Error 2

Do not report this issue to Homebrew/brew or Homebrew/core!

Brew is trying to install openssl 1.1.1l:

==> Downloading https://www.openssl.org/source/openssl-1.1.1l.tar.gz
Already downloaded: /Users/user/Library/Caches/Homebrew/downloads/b6ccc5a2a602c2af3480bbcf1656bd9844595974ba60501871ac12504508e818--openssl-1.1.1l.tar.gz

I need this dependency to install many other applications/tools, e.g., wget or python - and would like to use homebrew to do this.

The brew version I am using is:

Homebrew 3.2.9
Homebrew/homebrew-core (git revision fa395c6627; last commit 2021-08-27)
Homebrew/homebrew-cask (git revision 606ed52390; last commit 2021-08-27)

macOS is: 10.12.6 (Sierra) and I am using a MacBook Pro (13-inch, Early 2011)

Is there any way I can get around this issue to install openssl? Or anyway I can install python specifying a different openssl to use as a dependency?

I was able to install openssl 1.0 using the following brew command:

brew install rbenv/tap/[email protected]

However, python continually tries to use openssl 1.1.1l which is failing with the above error.

Answer 1

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

Answer 2

I had to change the following file on Sierra (MacOs 10.12):

sudo chmod a+w /Library/Developer/CommandLineTools/SDKs/MacOSX.sdk/usr/include/CommonCrypto/CommonRandom.h

vi /Library/Developer/CommandLineTools/SDKs/MacOSX.sdk/usr/include/CommonCrypto/CommonRandom.h

I've added the following line before the typedef statement:

#include "CommonCrypto/CommonCryptoError.h"

And also followed the advice of @Hulkur - run command:

brew edit openssl

and added

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

to args array in configure_args.

Answer 3

Seems a bug of openssl itself. https://github.com/openssl/openssl/issues/16487

---

~~What about export SDKROOT="/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk "?~~

---

Homebrew pre-build packages for some versions of macOS. But it keep dropping this pre-building support for old macOS. On macOS 10.12, you're building openssl from the source code and Xcode command line tool is needed.

xcode-select --install

Then brew install openssl again.

Answer 4

First, to edit the file:

$ export EDITOR=nano
$ export VISUAL="$EDITOR"

then

brew edit openssl

After file open add the line -I/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk/usr/include

 # help debug inevitable breakage.
  def configure_args
    args = %W[
      --prefix=#{prefix}
      --openssldir=#{openssldir}
      no-ssl3
      no-ssl3-method
      no-zlib
      -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

Save edition and install

brew install openssl 

Notice: the installation took a long time, but it's worked.

Answer 5

I had the same issue in Mac Sierra 10.13.6 (17G14042)

brew install [email protected]

I have updated the openssl

brew edit openssl

add the line inside def configure_args

-I/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk/usr/include
def configure_args 
  args = %W[
    --prefix=#{prefix}
    --openssldir=#{openssldir}
    no-ssl3
    no-ssl3-method
    no-zlib
    -I/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk/usr/include
  ]

Run the below comment after this.

RUBY_CONFIGURE_OPTS="--disable-install-doc --with-openssl-dir=$(brew --prefix [email protected])" rbenv install 3.0.2