In my make.conf I have: DEFAULT_VERSIONS+= ... ssl=libressl python=3.9 ... The py-cryptography package is built due to dependencies, and it is linked to base openssl instead of ports libressl: # tar xf packages/All/py39-cryptography-41.0.4,1.pkg tar: Removing leading '/' from member names # ldd usr/local/lib/python3.9/site-packages/cryptography/hazmat/bindings/_rust.abi3.so libssl.so.111 => /usr/lib/libssl.so.111 (0x24f070421000) libcrypto.so.111 => /lib/libcrypto.so.111 (0x24f07147d000) ...
I should mention I am on 13.2-STABLE: stable/13-c2c7340fef
As of HEAD 6b5a47c1f, this problem seems to have gone away. I am only leaving this open in case someone wants to investigate why this happened.