My problem is as follows:

I have installed Debian on an Encrypted Hard Drive with a USB flash drive boot key

So /boot is on USB drive the rest is on the encrypted hard drive.

First setup i made the harddisk with a passphrase and then i made a random data 4 kilobyte key file to unlock my harddrive.

This file is /boot/keyfile.gpg

It worked fine, i just insert my usb flash drive and it will start my Debian OS and decrypts the hard drive for me.

Then the problem started. The USB flash drive stopped working, if i start it it says there is no operating system. So i can't start from the USB drive.


Luckely i also have another hard disk in my system with Mint installed. So if i boot into Mint and look at the mounted drives i can see the encrypted drive. I still have (the non booting usb drive) with the keyfile.gpg on it, but i have no idea how i can use that keyfile to decrypt my hard drive. If i click the harddrive it wants a passphrase and there is no option to load a keyfile.

So in my opinion i have 2 option:
1. Make the USB drive bootable again, without destroying the /root and keyfile
2. Decrypt the hard drive with some tool using the keyfile.

What is the best (and working) method to decrypt my drive and get the data off and then reinstall the OS again?

You didn't mention your USB drive backup. If you didn't back up, that's a newbie error.

What goes wrong when you try to boot from the USB drive?

Yes you are correct, i didn't back up my USB drive...

If i boot from my USB drive it says no operating system, it looks like the USB is not bootable anymore. I can still open it (in mint) and see the files on it. but no more booting...

Have a look at the manpage for cryptsetup - you should be able to use the open command with --key-file.

I've never known anyone who encrypted a hard drive who did not subsequently sorely regret it.

Rubbish !!!.
I've got one that has never been breached - not even by me ...

Nah, gotta agree - waste of f'ing effort. The spooks already know everything, or can get it. The crims just ask the spooks for it ... :shrug:

Cynic ... me ???

Is it an issue with the drive or with grub/lilo?