This sounds like a Known Issue in the ReleaseNotes of Ubuntu 14.04:

https://wiki.ubuntu.com/TrustyTahr/ReleaseNotes#Known_issues
When using installer to upgrade or reinstall an existing installation with 
encrypted swap, the installer may fail to reuse the partition. A warning will 
be shown, however the installation can be completed. The installed system will 
not have swap activated and users are advised to recreate swap on their 
systems. Please see advice about adding and activating swap at: 
https://help.ubuntu.com/community/SwapFaq (Bug #1066342)

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

Title:
  Encrypted swap no longer mounted at bootup

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