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Bolt-On Security the Linux Way

Submitted by Roy Schestowitz on Thursday 13th of May 2021 03:40:41 AM Filed under
Security
HowTos

As longtime readers know, while I try to stay knowledgeable on the many sub-disciplines of information technology, my passion is for information security. Since it’s been a while since I’ve contributed any InfoSec knowhow, I wanted to rectify that. I couldn’t have timed this realization better, because (as you’ll see) the techniques on display are perfect for protecting your deluge of tax season documents.

In this piece, I aim to provide a range of simple but effective options for encrypting a small number of files. In particular, these options are salient for use cases like tax filing, where users are sending sensitive documents to recipients with an unknown degree of technical proficiency. Fond as I am of PGP, I’ll bet you your refund check that your accountant doesn’t know the first thing about using it.

Before going further, I’ll note that all of these file encryption techniques require you to use an additional channel for transmitting shared secrets, primarily passwords. The file will be sent through one pre-agreed channel, while the means of decrypting it will be sent via another.

There are too many viable auxiliary channels to enumerate, but just make sure that you take reasonable steps to pick one that isn’t easily compromised. The fact that you are using an additional channel is itself protection against the file’s compromise: without it, sending an encrypted file and its decryption password on the same channel creates a single point of failure. Using two channels requires two successful attacks by your adversaries to fail.

Let’s start at the lowest complexity (and security) technique and go to the highest. Some later entries are for the hardcore security types, but there’s something for everyone.

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