The closest thing I have found is this other thread on this forum - Any interests in Kernel 4.0 on My book live?
And also this tutorial on doing a clean Debian installation on a MyBook Live - https://www.schwabenlan.de/en/blog/2015/04/06/clean-debian-install-on-mybook-live-nas
These both sound like things that would enable the installation of later versions of openssl but I simply do not have enough knowledge personally to understand what I would be doing if I followed these. My Linux knowledge is pretty basic and has mostly come from following tutorials to the letter to install additional apps on my last 3 MyBook NAS drives and also some beginner Raspberry Pi work. I suppose I could always restore the MyBook Live from a disk image if anything went wrong but I just don’t think I’d be able to get it up and running as a NAS drive with SickRage, Transmission and Twonky from scratch on my own. I might have to upgrade to a MyCloud for later openssl support.
