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Old 12-27-2015, 11:42 AM   #1
LQ Newbie
Registered: Dec 2015
Location: California
Distribution: Debian 8
Posts: 3

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Debian 8 encryption password -- headless?

Newbie, recent build Debian 8, will use as home server. I followed an installation guide I found online which suggested using an "encryption password" that encrypts files on the discs for security. I did that. This means I must type in encryption password as part of the boot process.

My concern is this appears to mean the box cannot be truly headless. I cannot connect with my Windows machine until the Linux boot process is complete, and if typing in a password is part of that process, I cannot make the machine headless but must connect a keyboard and monitor every time I boot the Linux machine.

I understand Linux machines are not rebooted often, and if it is used as a home server that will certainly be the case.

Do most people use an encryption password for the disks on a server, or is that mainly for a desktop box? If encryption is used, is there a way to have server boot and require password later? I plan to later install/use SAMBA for home server connecting with Windows machines. Will that provide the security I need?

My wish is to make the machine truly headless so on the rare occasion I do reboot the machine, I can let it boot by itself and then I can connect using my Windows machine to monitor server functions.

When it boots, it also wants a user/password. I have not tried it due to encryption password, but if Linux server needs user/pass does that also mean I can't connect with Windows box until after user/pass is in? How do I get around that if the Linux machine is headless?

What steps do I need to take to ensure machine is truly headless and can boot on its own and I can simply connect with Windows box after automatic boot processes are complete, yet maintain system security?

I've tried some searching but not found anything that addresses this directly. If there are any online resources that directly address this concept, love to hear about it. Thanks

Old 12-27-2015, 08:21 PM   #2
Tim Abracadabra
Registered: May 2014
Location: USA, Wherever I may Roam
Distribution: Debian w/Xfce, LFS 7.9, ++
Posts: 117

Rep: Reputation: Disabled
I've tried some searching but not found anything that addresses this directly. If there are any online resources that directly address this concept, love to hear about it. Thanks
Found a number of links using:

Some methods include installing busybox with dropbear and compile them into the initramfs
which will enable you to ssh in to enter the decryption passphrase.

Note the security implications. You might want to enable this early ssh capability only on an internal non-internet accessible network if you can (Possibly using a second network card (wired) in both the server and the ssh client box).

Hopefully that gives you a start.

All the best,

Last edited by Tim Abracadabra; 12-27-2015 at 08:42 PM. Reason: alter redundant closing, add wired, only


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