A solution to making this work remotely is:

1) SSH in
2) Manually run cryptsetup; basically run ps, find the cryptsetup command-line, 
remote the key-file option, run it, type the password into cryptsetup
3) kill cryptsept process, kill plymouth process

It just worked for me:-)

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https://bugs.launchpad.net/bugs/595648

Title:
  Remote unlocking not possible if plymouth is active (Bug or Feature?)

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