Hi @Tdickson3!

It looks like this error message impacts several different Python-based projects:

• Running flask crashes Python on macOS 10.15 pallets/flask#3329
• OS X binaries don't work with Homebrew Python [OS X 10] numenta/nupic-legacy#1813

So it's probably an issue with Python or a library and not pip specifically. I would check with whatever Python distributor you're using (homebrew?). Some information here may also be useful.

I hope that helps! This doesn't appear to be a pip problem so I'll close this eagerly, but please let us know if you have any other evidence that point to pip being at fault. Thanks!

I had the same issue and was able to resolve following the steps from this thread:

https://forums.developer.apple.com/thread/119429

For me, this issue was related to the libssl.1.0.0.dylib and libcrypto.1.0.0.dylib. The python.log file provided by the OP references libcrypto dylib as well.

from python.log file:
Invalid dylib load. Clients should not load the unversioned libcrypto dylib as it does not have a stable ABI.

for anyone who finds this, you can view your own python log files at ~/Library/Logs/DiagnosticReports.

someone else might be able to explain this further, but in short, the error seems to be related to Catalina not allowing un-versioned dylibs to be called. The solution is to link the un-versioned dylib files to ones with a version. Below are steps taken from the prevailing answer in the above link, and I can confirm that they worked for me. It doesn't seem like existing virtual environments will be fixed with the below, but after the fix you can create new virtual environments and they should behave as expected.

Steps to Fix
in your terminal:

1. brew update && brew upgrade && brew install openssl
   ##note: some people report that the dylib files needed in pip install --editable and pip install clash for namespace packages #3 are in the 1.0.2t folder, rather than the lib folder. adjust your path in pip install -r requirements.txt doesn't know when package installation fails during native compilation #2 as needed.
2. cd /usr/local/Cellar/openssl/1.0.2t/lib
3. sudo cp libssl.1.0.0.dylib libcrypto.1.0.0.dylib /usr/local/lib/
4. cd /usr/local/lib
5. sudo ln -s libssl.1.0.0.dylib libssl.dylib
6. sudo ln -s libcrypto.1.0.0.dylib libcrypto.dylib

@Esolberg2 Thank you for your help！

This is related to pyopenssl using old dependencies. You can fix it by removing the cryptography package, then upgrading cryptography to version 2.8.

You can also add to your .bashrc following line:

export DYLD_LIBRARY_PATH=/usr/local/Cellar/openssl/1.0.2t/lib