Why I've Retired My PGP Keys and What's Replaced It

Update August 2019: I’ve got a PGP key again but only for signing. I use another of my own tools, passphrase2pgp, to manage it.

tl;dr: Enchive (rhymes with “archive”) has replaced my use of GnuPG.

Two weeks ago I tried to encrypt a tax document for archival and noticed my PGP keys had just expired. GnuPG had (correctly) forbidden the action, requiring that I first edit the key and extend the expiration date. Rather than do so, I decided to take this opportunity to retire my PGP keys for good. Over time I’ve come to view PGP as largely a failure — it never reached the critical mass, the tooling has always been problematic, and it’s now a dead end. The only thing it’s been successful at is signing Linux packages, and even there it could be replaced with something simpler and better.

I still have a use for PGP: encrypting sensitive files to myself for long term storage. I’ve also been using it to consistently to sign Git tags for software releases. However, very recently this lost its value, though I doubt anyone was verifying these signatures anyway. It’s never been useful for secure email, especially when most people use it incorrectly. I only need to find a replacement for archival encryption.

I could use an encrypted filesystem, but which do I use? I use LUKS to protect my laptop’s entire hard drive in the event of a theft, but for archival I want something a little more universal. Basically I want the following properties:

I couldn’t find anything that fit the bill, so I did exactly what you’re not supposed to do and rolled my own: Enchive. It was loosely inspired by OpenBSD’s signify. It has the tiny subset of PGP features that I need — using modern algorithms — plus one more feature I’ve always wanted: the ability to generate a keypair from a passphrase. This means I can reliably access my archive keypair anywhere without doing something strange like uploading my private keys onto the internet.

On Enchive

Here’s where I’d put the usual disclaimer about not using it for anything serious, blah blah blah. But really, I don’t care if anyone else uses Enchive. It exists just to scratch my own personal itch. If you have any doubts, don’t use it. I’m putting it out there in case anyone else is in the same boat. It would also be nice if any glaring flaws I may have missed were pointed out.

Not expecting it to be available as a nice package, I wanted to make it trivial to build Enchive anywhere I’d need it. Except for including stdint.h in exactly one place to get the correct integers for crypto, it’s written in straight C89. All the crypto libraries are embedded, and there are no external dependencies. There’s even an “amalgamation” build, so make isn’t required: just point your system’s cc at it and you’re done.


For encryption, Enchive uses Curve25519, ChaCha20, and HMAC-SHA256.

Rather than the prime-number-oriented RSA as used in classical PGP (yes, GPG 2 can do better), Curve25519 is used for the asymmetric cryptography role, using the relatively new elliptic curve cryptography. It’s stronger cryptography and the keys are much smaller. It’s a Diffie-Hellman function — an algorithm used to exchange cryptographic keys over a public channel — so files are encrypted by generating an ephemeral keypair and using this ephemeral keypair to perform a key exchange with the master keys. The ephemeral public key is included with the encrypted file and the ephemeral private key is discarded.

I used the “donna” implementation in Enchive. Despite being the hardest to understand (mathematically), this is the easiest to use. It’s literally just one function of two arguments to do everything.

Curve25519 only establishes the shared key, so next is the stream cipher ChaCha20. It’s keyed by the shared key to actually encrypt the data. This algorithm has the same author as Curve25519 (djb), so it’s natural to use these together. It’s really straightforward, so there’s not much to say about it.

For the Message Authentication Code (MAC), I chose HMAC-SHA256. It prevents anyone from modifying the message. Note: This doesn’t prevent anyone who knows the master public key from replacing the file wholesale. That would be solved with a digital signature, but this conflicts with my goal of encrypting files without the need of my secret key. The MAC goes at the end of the file, allowing arbitrarily large files to be encrypted single-pass as a stream.

There’s a little more to it (IV, etc.) and is described in detail in the README.


The first thing you’d do is generate a keypair. By default this is done from /dev/urandom, in which case you should immediately back them up. But if you’re like me, you’ll be using Enchive’s --derive (-d) feature to create it from a passphrase. In that case, the keys are backed up in your brain!

$ enchive keygen --derive
secret key passphrase:
secret key passphrase (repeat):
passphrase (empty for none):
passphrase (repeat):

The first prompt is for the secret key passphrase. This is converted into a Curve25519 keypair using an scrypt-like key derivation algorithm. The process requires 512MB of memory (to foil hardware-based attacks) and takes around 20 seconds.

The second passphrase (or the only one when --derive isn’t used), is the protection key passphrase. The secret key is encrypted with this passphrase to protect it at rest. You’ll need to enter it any time you decrypt a file. The key derivation step is less aggressive for this key, but you could also crank it up if you like.

At the end of this process you’ll have two new files under $XDG_CONFIG_DIR/enchive: enchive.pub (32 bytes) and enchive.sec (64 bytes). The first you can distribute anywhere you’d like to encrypt files; it’s not particularly sensitive. The second is needed to decrypt files.

To encrypt a file for archival:

$ enchive archive sensitive.zip

No prompt for passphrase. This will create sensitive.zip.enchive.

To decrypt later:

$ enchive extract sensitive.zip.enchive

If you’ve got many files to decrypt, entering your passphrase over and over would get tiresome, so Enchive includes a key agent that keeps the protection key in memory for a period of time (15 minutes by default). Enable it with the --agent flag (it may be enabled by default someday).

$ enchive --agent extract sensitive.zip.enchive

Unlike ssh-agent and gpg-agent, there’s no need to start the agent ahead of time. It’s started on demand as needed and terminates after the timeout. It’s completely painless.

Both archive and extract operate stdin to stdout when no file is given.

Feature complete

As far as I’m concerned, Enchive is feature complete. It does everything I need, I don’t want it to do anything more, and at least two of us have already started putting it to use. The interface and file formats won’t change unless someone finds a rather significant flaw. There is some wiggle room to replace the algorithms in the future should Enchive have that sort of longevity.

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Chris Wellons

wellons@nullprogram.com (PGP)
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