I’ve got it working. I included my libssl.so in Engine/Build/Android/Java/jni and edited the Android makefile (similar to what’s done here: Android Java Libraries in UE4 Game (OUYA SDK, Google Play Game Services, etc.) - Mobile - Unreal Engine Forums) and then made my own dlopen call to open with the RTLD_GLOBAL flag before the python initialization that had the failing dlopen.
It didn’t seem to work if the python library had an explicit dependency on a libssl.so written into it’s file, or if my libssl.so had the same soname as the default Android one, so I compiled a versions of the libraries where those weren’t the case.