I was successful following the guide here: http://paxswill.com/blog/2013/11/04/enc ... pberry-pi/
When I boot the Pi, it drops to an initramfs prompt, then I unlock the partition with
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# cryptsetup luksOpen /dev/mmcblk0p2 sdcard
# exit
and it boot up to Debian. Great!
However, there are some issues. When I try to update the initramfs file with
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# sudo mkinitramfs -o /boot/initramfs.gz
The second issue is that I did not properly configure dropbear; it appears to be configured to use DHCP, which means that when I log in it gets some random IP address. I need to update the configuration to a fixed IP so that I can log in headless after a reboot, but without the ability to update the initramfs, I don't know how to fix this.
Given that I can't even get an initramfs prompt after the update, I'm really not sure how to even start solving this problem, so any hints would be great. I'll provide whatever information that will be helpful.