Python crashing on MacOS 10.15 Beta (19A582a) with "/usr/lib/libcrypto.dylib"

For me it was enough to re-install Python's cryptography package.

pip uninstall cryptography
pip install cryptography

I just came across the same problem and felt a bit uncomfortable to manually link things around.

I was able to solve the problem by simply

1. Installing openssl via homebrew:

   brew install openssl
   

2. Pointing towards the dynamic libraries from openssl via DYLD_LIBRARY_PATH:

   export DYLD_LIBRARY_PATH=/usr/local/opt/openssl/lib:$DYLD_LIBRARY_PATH
   

I've just added that line to my .zshrc.

Edit: According to this question, the usage of DYLD_FALLBACK_LIBRARY_PATH might be preferable over DYLD_LIBRARY_PATH.

Edit 2: As mentioned in a comment below, this should probably be the accepted answer. Simply reinstall the cryptography package.

I prefer a combination of @bixel, @Juro Oravec & @honkaboy answers:

brew install openssl
cd /usr/local/lib
sudo ln -s /usr/local/opt/openssl/lib/libssl.dylib libssl.dylib
sudo ln -s /usr/local/opt/openssl/lib/libcrypto.dylib libcrypto.dylib

This way, at least in theory, when updating openssl the dylibs will always point to the latest versions. /usr/local/opt/openssl is actually a link to /usr/local/Cellar/openssl/Cellar/openssl/1.0.2t (the version of openssl installed by brew).

The reason the issue happens is actually explained by brew:

openssl is keg-only, which means it was not symlinked into /usr/local, because Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries.

Trying to run brew link openssl:

Warning: Refusing to link macOS-provided software: openssl If you need to have openssl first in your PATH run: echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile

For compilers to find openssl you may need to set: export LDFLAGS="-L/usr/local/opt/openssl/lib" export CPPFLAGS="-I/usr/local/opt/openssl/include"

For pkg-config to find openssl you may need to set: export PKG_CONFIG_PATH="/usr/local/opt/openssl/lib/pkgconfig"

So, basically you need to link them manually.

Caveat: I am not a security expert, and this solution messes with crypto libraries!

I don't think your issue stems from zsh or oh-my-zsh. My best guess: some crypto libraries installed with MacOS 10.15 are incompatible with Homebrew's python3 installation.

Here's what fixed the issue for me

# Install openssl via homebrew.
# Note: According to homebrew, "openssl is keg-only, which means it was
# not symlinked into /usr/local, because Apple has deprecated use of
# OpenSSL in favor of its own TLS and crypto libraries."
brew install openssl
# Symlink those versions into /usr/local/lib, which gets Python to dynamically
# link against those instead of the version in /usr/lib/.
# Got the idea from https://forums.developer.apple.com/thread/119429
cd /usr/local/lib
sudo ln -s /usr/local/Cellar/openssl/1.0.2t/lib/libssl.1.0.0.dylib libssl.dylib
sudo ln -s /usr/local/Cellar/openssl/1.0.2t/lib/libcrypto.1.0.0.dylib libcrypto.dylib

My situation for context:

• Recently upgraded to MacOS 10.15
• I use python/pip installed via homebrew: brew install python
• pip3 was failing with SIGABRT

Header of system error report:

Process:               Python [52429]
Path:                  /usr/local/Cellar/python/3.7.4_1/Frameworks/Python.framework/Versions/3.7/Resources/Python.app/Contents/MacOS/Python
Identifier:            Python
Version:               3.7.4 (3.7.4)
Code Type:             X86-64 (Native)
Parent Process:        zsh [43309]
Responsible:           iTerm2 [2316]
User ID:               501

Date/Time:             2019-10-09 09:52:18.148 -0700
OS Version:            Mac OS X 10.15 (19A583)
Report Version:        12
Bridge OS Version:     4.0 (17P572)
Anonymous UUID:        

Sleep/Wake UUID:       

Time Awake Since Boot: 9900 seconds
Time Since Wake:       7300 seconds

System Integrity Protection: enabled

Crashed Thread:        0  Dispatch queue: com.apple.main-thread

Exception Type:        EXC_CRASH (SIGABRT)
Exception Codes:       0x0000000000000000, 0x0000000000000000
Exception Note:        EXC_CORPSE_NOTIFY

Application Specific Information:
/usr/lib/libcrypto.dylib
abort() called
Invalid dylib load. Clients should not load the unversioned libcrypto dylib as it does not have a stable ABI.