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Hi my crypttab looks as follows:

crypt_device /dev/sda luks,header=/boot/header.img

update-initramfs -u -k all works with success, but for some reason cryptsetup will not find the header.img which resides on the usb stick (that also contains the boot partition) during boot. It is stored on /boot/header.img

(using luks encryption with detached header, and seperate boot partition on usb, os: lubuntu 18)

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Unless you've taken special steps to mount the /boot filesystem under initramfs, it won't be mounted yet. In a default boot sequence, the system only cares about the root filesystem (and possibly the swap partition) while executing in initramfs.

Once the real root filesystem has been checked (if applicable) and mounted, the rest of the filesystems, normally including /boot, are mounted. You would need to make some special arrangement to mount the /boot filesystem while still in initramfs to gain access to /boot/header.img. Or you could just include your header.img into initramfs.

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