macOS 10.12 brew install openssl issue - macos

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/openssl#1.1\"" -DENGINESDIR="\"/usr/local/Cellar/openssl#1.1/1.1.1l/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/openssl#1.0
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

I had the same issue in Mac Sierra 10.13.6 (17G14042)
brew install openssl#1.1
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 openssl#1.1)" rbenv install 3.0.2

Answer 5

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 6

After brew edit openssl, I end up with a new error:
=> perl ./Configure --prefix=/usr/local/Cellar/openssl#1.1/1.1.1l --openssldir=/usr/local/etc/openssl#1.1 no-ssl3 no-ssl3-method no-zlib -I/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk/usr/include darwin64-x86_64-cc enable-ec_nistp_64_gcc_128
==> make
Last 15 lines from /Users/francis/Library/Logs/Homebrew/openssl#1.1/02.make:
include "CommonCrypto/CommonCryptoError.h"
^
/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk/usr/include/CommonCrypto/CommonRandom.h:35:9: error: expected identifier or '('
include "CommonCrypto/CommonCryptoError.h"
^
/Library/Developer/CommandLineTools/SDKs/MacOSX.sdk/usr/include/CommonCrypto/CommonRandom.h:52:1: error: unknown type name 'CCRNGStatus'
CCRNGStatus CCRandomGenerateBytes(void *bytes, size_t count)
^
crypto/rand/rand_unix.c:385:47: error: use of undeclared identifier 'kCCSuccess'
if (CCRandomGenerateBytes(buf, buflen) == kCCSuccess)
^
4 errors generated.
make[1]: *** [crypto/rand/rand_unix.o] Error 1
make[1]: *** Waiting for unfinished jobs....
make: *** [all] Error 2
Edit
Silly me, I had:
include "CommonCrypto/CommonCryptoError.h"
Instead of
#include "CommonCrypto/CommonCryptoError.h"
So make sure you have a hash first.

Answer 7

This issue has now been resolved (since 9/11/2021) and patches are no longer required

Answer 8

For MacOS prior to 10.12 (e.g. 10.11 El Capitan) there is another issue - test failure:
Test Summary Report
-------------------
../test/recipes/05-test_rand.t (Wstat: 256 Tests: 2 Failed: 1)
Failed test: 1
Non-zero exit status: 1
Files=1, Tests=2, 5 wallclock secs ( 0.38 usr 0.06 sys + 5.71 cusr 2.48 csys = 8.63 CPU)
Result: FAIL
make[1]: *** [_tests] Error 1
make: *** [tests] Error 2
There is an issue and a pull request for OpenSSL that is open to fix this:
https://github.com/openssl/openssl/issues/16517
https://github.com/openssl/openssl/pull/16587
If you have this issue go over and vote for them