I just encountered the problem that I have to type two passwords at startup, for two encrypted disks. My first disk is encrypted through the Ubuntu installer. After some searching I found the perfect solution for that task. In German its called "Schlüsselableitung", in English derived keys. But perfect solutions often have a big issue why they don’t work, like here. I’m using Ubuntu 16.04 which uses ´systemd´, and that has problems with derived keys. So I found the second most perfect solution for me, using a key-file. Some people argue that this is a security issue, but the derived key is also obtainable with root rights, just like a key-file. And by the way, your private keys of your certificates are also stored on that disks and nearly nobody complains about that.