Ah, maybe it’s purely a package problem then. But if you load the JLL OpenSSL before the Python one in a session with PythonCall, and the two versions are not the same, Python will not be able to successfully call into OpenSSL. (There’s a fix for this in CondaPkg.jl for this exact reason).
I guess the problem is getting Pkg info to Conda, from the Conda end…(since the Julia/Pkg end is solved via CondaPkg!)
A bigger problem is coordinating JLL versions between different packages, since Julia JLLs often don’t share the upstream project’s exact version number (take Proj_jll as an example, which multiplies all version numbers by 100).