Could this be the cause?  I just noticed this comment...

<blockquote>If your system seems to hang while booting, try pressing a
few keys. Since we use /dev/random for the swap encryption key, the
system may have run out of usable entropy while making the random swap
encryption key. Pressing keys will give it some entropy to
use.</blockquote>

>From https://help.ubuntu.com/community/EncryptedFilesystemHowto5

It seems about right.  For me it's several keypresses that are required.

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Upstart needs some key pressed to show "Enter Passphrase" on boot /  cryptsetup 
problem
https://bugs.launchpad.net/bugs/105394
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