The messages from aptermlog seem relevant:

update-initramfs: Generating /boot/initrd.img-4.15.0-38-generic
cryptsetup: WARNING: Option 'size' missing in crypttab for plain dm-crypt 
    mapping cryptswap1. Please read /usr/share/doc/cryptsetup/README.initramfs 
and 
    add the correct 'size' option to your crypttab(5).
cryptsetup: ERROR: Couldn't resolve device /swapfile
cryptsetup: WARNING: Resume target cryptswap1 uses a key file
update-initramfs: Generating /boot/initrd.img-4.15.0-36-generic
cryptsetup: WARNING: Option 'size' missing in crypttab for plain dm-crypt 
    mapping cryptswap1. Please read /usr/share/doc/cryptsetup/README.initramfs 
and 
    add the correct 'size' option to your crypttab(5).
cryptsetup: ERROR: Couldn't resolve device /swapfile
cryptsetup: WARNING: Resume target cryptswap1 uses a key file

** Package changed: ubuntu-release-upgrader (Ubuntu) => cryptsetup
(Ubuntu)

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https://bugs.launchpad.net/bugs/1802617

Title:
  After upgrade to 18.10 boot fails on waiting for encrypted source
  device

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