showed the start job for a device timing out and directly afterwards failing the cryptography setup of a device referenced as cr_usb-General_USB_Flash_Disk. I am unsure whether the two are connected.
They are. The UUID of the timed-out device is the same UUID referenced in the crypttab.
[ TIME ] Timed out waiting for device dev-disk-by\x2duuid-00a69115\x2d956d\x2d41b3\x2d830c\x2d9a3878087d41.device.
[DEPEND] Dependency failed for Cryptography Setup for cr_usb-General_USB_Flash_Disk_0349315060001623-0:0-part2.
/etc/crypttab
cr_sda2 UUID=7f99168c-4972-468b-900f-fb5bbfb90e66
cr_usb-General_USB_Flash_Disk_0349315060001623-0:0-part2 UUID=00a69115-956d-41b3-83