Okay, here's what I do to fix the problem (for 14.04). I'll break it
down into three steps.

1. Reformat the original swap partition on the system and make note of
it's new uuid. You need to do this, because ubuntu wipes the uuid when
it encrypts the partition on the first boot.

2. Now change /etc/crypttab to include an offset of 10MiB (offset=20) so that 
cryptdisks doesn't wipe the uuid on the new swap partition.
Change from:
cryptswap1 UUID="old-uuid" /dev/urandom swap,cipher=aes-cbc-essiv:sha256
To:
cryptswap1 UUID="new-uuid" /dev/urandom 
swap,cipher=aes-cbc-essiv:sha256,offset=20

3. Now run the following commands to activate the encrypted swap partition:
   sudo cryptdisks_start cryptswap1
   sudo swapon -a

This should fix the issue, and the system should automatically have an
active encrypted swap on each subsequent boot.

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https://bugs.launchpad.net/bugs/953875

Title:
  Encrypted swap no longer mounted at bootup

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