Almost any kind of crash is possible when using ctypes.  But you almost certainly don't want to be loading /usr/lib/libcrypto.dylib.  That's the macOS legacy version which is there only for legacy Apple-supplied third-party components, like the Apple-supplie system Python.  Apple doesn't even supply the header files for the system libssl and libcrypto deliberately so you are not supposed to be able to successfully link with them.  So you should try to figure out why asn1crypto is apparently linked with it.  It should likely be trying to link with a libcrypto provided by Homebrew openssl.  Good luck.