Sorry for the slow reply, life occurred.

I think I understand where you’re coming from with the desired to be productive and not reinstall. I think I’ve been there too! One thing that I can suggest, if you do have the time, is to learn a system like Ansible and use it to setup and configure your machine. The discipline of keeping all of the config as source rather than making ad-hoc changes reduces the chance of thinking you’ll make just one little change and breaking something, and, if something does go wrong, you can get back to your working configuration quickly.

Bearing in mind that there really isn’t anything you can do to stop yourself if you’re really determined to not lose the data, because if you can read it at any time you can back it up, the closest you are likely to come is something like creating new key with GPG then using the TPM to wrap your secret key and deleting the original. That way the key is only usable on that specific machine. Then use the key-pair to encrypt your ‘guard’ files. You can still decrypt them because you have the wrapped secret keys and you’re on the same machine, but if you wipe the drive and lose those keys the data is gone. The TPM wrapping prevents you from taking the keys to a different machine to decrypt your data.

There’s an article with some examples here,

Having said all of that, this still doesn’t help if you just clone the disk as all of the data, including the wrapped key and the encrypted files will be cloned. The one difference there is that the serial number of the hard drive will be different. Maybe you could use that, combined with a passphrase as the passphrase for your GPG key, but we’re getting into pretty esoteric territory here. So you could generate a secret key with a command like:

( lsblk -dno SERIAL /dev/sdb ; zenity --title "Enter decrypt password" --password) | sha1sum | cut -c1-40

Where /dev/sdb is the device your root partition is on. zenity is a handy utility for displaying dialogs, there are others available. In this use it just prompts for a passsword. We then concatenate the drive serial number from lsblk with the password you entered and hash the result. The hashing is really only a convenient way to mix the two without worrying about the newline lsblk spits out. Don’t record the result of this command, but use it to set the passphrase on your new GPG key. Wrapping the secret key in the manner the article above suggests is a nice extra step to make it harder to move the drive to another machine or mess around in that sort of way, but not strictly necessary as that wasn’t in the scope of your original question.

Now you can encrypt your file with: gpg -e -r <your key name> <your file>'. That will produce an encrypted version of <your file>called<your file>.gpg. To decrypt the file you can get gpg` to use the hashing command from above to get the passphrase with something like:

gpg -d --pinentry-mode=loopback --batch --passphrase-fd 3 <your file>.gpg 3< <( ( lsblk -dno SERIAL /dev/sdb ; zenity --title "Enter decrypt password" --password) | sha1sum | cut -c1-40 )

Once you’ve tested that you can decrypt the file successfully you can remove the original, plaintext, file. Your data is now encrypted with a key that is secured with a passphrase made of a string you know and the serial number of your disk and optionally wrapped with a key from the TPM that is tied to your physical machine. If you change the disk or the machine the data is irretrievable (ignoring the caveats discussed above). I think that’s about as close to your original goal as you can get. It’s rough around the edges, and I’m not sure I’d trust my data to it, but I believe it’ll work. If you do something like this, please test it thoroughly, I can’t guarantee it!

‘This post is a palaeontological disaster’ is a marvelous turn of phrase, and I intend to steal it for use at the first opportunity.

Well yes, humpback whales reach sexual maturity by around 10 years of age (some much before then it seems). A marine biologist is still practically in it’s larval form at that point.

(Yes, yes, I know that wasn’t what you meant, but I couldn’t help myself)

Crabadile - the ultimate lifeform.

This seems like a very complicated way to achieve your goal! It sounds like sitting yourself down and giving you a stern talking to might be a beter aporoach.

Having said that, if you have these very important files that you don’t want to lose, please make sure they’re backed up somewhere off of your machine. Storage fails, and it’s a horrible feeling losing something important. Unfortunately doing so would defeat the approach you’re thinking of.

This might be a case of needing to reframe the question to get to the cause of the issue, and then solve that. So, why do you want to make it hard to reinstall your machine? Is it the amount of time you spend on it, the chance of screwing it up, needing it working, has it become a compulsion or something else? Maybe if we can get to the root of the issue we can find a solution.

With regard to TPM, it’s basically just a key store, so you can use it fir anything really, althought it’s normally used by generating a TPM key and using it to encrypt the key that’s actually used to encrypt your data, storing the encrypted key with the OS. Just reinstalling won’t wipe the TPM, but unless you made an effort to save the encrypted key it’ll be gone. Given your problem statement above it just adds to the data you’d need to save, which isn’t helpful.

Ok, I’m still not clear on exactly what you’re trying to achieve as I can’t quite see the connection between somehow preventing certain files being duplicated when cloning the disk and preventing yourself from reinstalling the system.

Bear in mind that reinstalling the system would replace all of the OS, so there’s no way to leave counter-measures there, and the disk itself can’t do anything to your data, even if it could detect a clone operation.

If what you’re trying to protect against is someone who knows everything you do accessing your data, you could look to use TPM to store the encryption key for your FDE. That way you don’t know the password, it’s stored encrypted with a secret key that is, in turn, stored and protected by your CPU. That way a disk clone couldn’t be used on any hardware except your specific machine.

Nothing can prevent a disk clone cloning the data, and there’s no way to make something happen when a disk is cloned as you’re not in control of the process.

If you wish to mask the existence of the files, use either full disk encryption, in which case cloning the disk doesn’t reveal the existence of the files without the decrypt password, or use a file based encrypted partition such as veracrypt in which case the cloner would just see a single encrypted blob rather than your file names.

Ultimately encrypting the files with gpg means they have already effectively ‘destroyed or corrupted’ themselves when cloned. If you don’t want to reveal the filenames, just call them something else.

If you could be a bit more specific about your threat model people may have better ideas to help.

It sounds like you’re actually more concerned about the data in the files not being able to ‘pop up’ elsewhere, rather than the files themselves. In thus case I’d suggest simply encrypting them, probably using gpg. That’ll let you set a password that is distinct from the one used for sudo or similar.

You should also be using full disk encryption to reduce the risk of a temporary file being exposed, or even overwritten sectors/pages being available to an attacker.

It looks like AssDB uses a weird SQL syntax? Is it worth upgrading to, I hear it’s great at pulling information out of unstructured and even imaginary data sources?

Ah, memories. That was me on a Spectrum. It’s all fun and games until you forget to save (to tape) and your code hangs the machine, losing everything.

Putting a simple preseed file on a debian install image is probably going to be your best bet. Assuming you can run a VM on your current machine it shouldn’t be too difficult to test it until you’re happy with it.

It’s going to be a balance between your time getting an automated approach to work and the cost/effort of getting a monitor. Getting preseed working can be a bit fiddly, but it does mean you’ve learnt a new skill, getting a monitor sounds like it’ll be a pain, and you might only need it once.

Yes, that’ll work too, it does involve adding the disk to your machine temporarily though, so just be carefully which disk you format to do it. Please don’t ask why I say that, it brings back painful memories…

While I agree with most people here that finding a keyboard and screen would be the easiest option, you do have a couple of other options:

• Use a preseed file A preseed lets the installer run completely automatically, without user intervention. Get it to install a basic system with SSH and take it from there. You’ll want to test the install in a VM, where you can see what’s going on before letting it run on the real server. More information here: https://wiki.debian.org/DebianInstaller/Preseed

• Boot from a live image with SSH Take a look at https://wiki.debian.org/LiveCD in particular ‘Debian Live’. It looks like ssh is included, but you’d want to check the service comes up on boot. You can then SSH to the machine and install to the harddrive that way. Again, test on a VM until you know you have the image working, and know how to run the install, then write it to a USB key and boot the tsrget server from that.

This all assumes the target server has USB or CD at the top of its boot order. If it doesn’t you’ll have to change that first, either with a keyboard and screen, or via a remote management interface sych as IPMI.

Tried with ‘Connect for lemmy’ against lemm.ee and just got a full screen error that vanished after a second.

/ etc / passwd <- so none of the components are blocked.

I, for one, welcome our immortal, time-travelling, hamster overlord, but please stop giving away their secrets. The ‘vapourisation’ is the cover they need to make the particularly tricky jumps through time and space. It’s not needed every time, hence why it’s not more common, just when they need to arrive at a very specific point that’s already crowded with other manifestations of the ur-hamster.

Of course they’re not blowing up the hamster! That would be unethical, immoral, probably illegal, very hard to clean up, and, most importantly, lasers don’t blow things up, they vapourise them.

They vapourise the hamsters.

Check the linked article, the issue is around how information that is technically true but presented in certain ways can influence people. They found that headlines that, for instance, said someone had died after being vaccinated had a significant effect on people’s intention to get vaccinated themselves, despite complications being very rare.

Basically people are easy to influence, and you don’t need to outright lie to do it, just presenting facts in an unbalanced way will do it. Many would call that lieing too, but it’s by omission rather than by fabrication.

Have you ever seen them both in the same room at the same time? I know I haven’t. :)

It’d be far more mortifying if it was the other way around!