Daniel Lange's blog

I've long said that the main tools in the Open Source security space, OpenSSL and GnuPG (gpg), are broken and only a complete re-write will solve this. And that is still pending as nobody came forward with the funding. It's not a sexy topic, so it has to get really bad before it'll get better.

Gpg has a UI that is close to useless. That won't substantially change with more bolted-on improvements.

Now Robert J. Hansen and Daniel Kahn Gillmor had somebody add ~50k signatures (read 1, 2, 3, 4 for the g{l}ory details) to their keys and - oops - they say that breaks gpg.

But does it?

I downloaded Robert J. Hansen's key off the SKS-Keyserver network. It's a nice 45MB file when de-ascii-armored (gpg --dearmor broken_key.asc ; mv broken_key.asc.gpg broken_key.gpg).

Now a friendly:

And the result is a nicely useable 3835 byte file of the clean public key. If you supply a keyring instead of --no-default-keyring it will also keep the non-self signatures that are useful for you (as you apparently know the signing party).

So it does not break gpg. It does break things that call gpg at runtime and not asynchronously. I heard Enigmail is affected, quelle surprise.

Now the main problem here is the runtime. 1h45min is just ridiculous. As Filippo Valsorda puts it:

Someone added a few thousand entries to a list that lets anyone append to it. GnuPG, software supposed to defeat state actors, suddenly takes minutes to process entries. How big is that list you ask? 17 MiB. Not GiB, 17 MiB. Like a large picture. https://dev.gnupg.org/T4592

If I were a gpg / SKS keyserver developer, I'd

• speed this up so the edit-key run above completes in less than 10 s (just getting rid of the lseek/read dance and deferring all time-based decisions should get close)
• (ideally) make the drop-sig import-filter syntax useful (date-ranges, non-reciprocal signatures, ...)
• clean affected keys on the SKS keyservers (needs coordination of sysops, drop servers from unreachable people)
• (ideally) use the opportunity to clean all keyserver filesystem and the message board over pgp key servers keys, too
• only accept new keys and new signatures on keys extending the strong set (rather small change to the existing codebase)

That way another key can only be added to the keyserver network if it contains at least one signature from a previously known strong-set key. Attacking the keyserver network would become at least non-trivial. And the web-of-trust thing may make sense again.

Updates

09.07.2019

GnuPG 2.2.17 has been released with another set of quickly bolted together fixes:

  * gpg: Ignore all key-signatures received from keyservers.  This
    change is required to mitigate a DoS due to keys flooded with
    faked key-signatures.  The old behaviour can be achieved by adding
    keyserver-options no-self-sigs-only,no-import-clean
    to your gpg.conf.  [#4607]
  * gpg: If an imported keyblocks is too large to be stored in the
    keybox (pubring.kbx) do not error out but fallback to an import
    using the options "self-sigs-only,import-clean".  [#4591]
  * gpg: New command --locate-external-key which can be used to
    refresh keys from the Web Key Directory or via other methods
    configured with --auto-key-locate.
  * gpg: New import option "self-sigs-only".
  * gpg: In --auto-key-retrieve prefer WKD over keyservers.  [#4595]
  * dirmngr: Support the "openpgpkey" subdomain feature from
    draft-koch-openpgp-webkey-service-07. [#4590].
  * dirmngr: Add an exception for the "openpgpkey" subdomain to the
    CSRF protection.  [#4603]
  * dirmngr: Fix endless loop due to http errors 503 and 504.  [#4600]
  * dirmngr: Fix TLS bug during redirection of HKP requests.  [#4566]
  * gpgconf: Fix a race condition when killing components.  [#4577]

Bug T4607 shows that these changes are all but well thought-out. They introduce artificial limits, like 64kB for WKD-distributed keys or 5MB for local signature imports (Bug T4591) which weaken the web-of-trust further.

I recommend to not run gpg 2.2.17 in production environments without extensive testing as these limits and the unverified network traffic may bite you. Do validate your upgrade with valid and broken keys that have segments (packet groups) surpassing the above mentioned limits. You may be surprised what gpg does. On the upside: you can now refresh keys (sans signatures) via WKD. So if your buddies still believe in limiting their subkey validities, you can more easily update them bypassing the SKS keyserver network. NB: I have not tested that functionality. So test before deploying.

10.08.2019

Christopher Wellons (skeeto) has released his pgp-poisoner tool. It is a go program that can add thousands of malicious signatures to a GNUpg key per second. He comments "[pgp-poisoner is] proof that such attacks are very easy to pull off. It doesn't take a nation-state actor to break the PGP ecosystem, just one person and couple evenings studying RFC 4880. This system is not robust." He also hints at the next likely attack vector, public subkeys can be bound to a primary key of choice.

Well, shortly after I wrote about encrypting files with a keyfile / passphrase with gpg people asked about a solution with openssl.

You should prefer to use the gpg version linked above, but if you can't, below is a script offering the same functionality with openssl.

You basically call crypt_openssl <file> [<files...>] to encrypt file to file.aes using the same keyfile as used in the gpg script (~/.gnupg/mykey001 per default).

A simple crypt_openssl -d <file.aes> [<files.aes...>] will restore the original files from the encrypted AES256 version that you can safely transfer over the Internet even using insecure channels.

Please note that you should feed compressed data to crypt_openssl whenever you can. So use preferably use it on .zip or .tar.gz files.

Automatically transferring (syncing) files between multiple computers is easy these days. Dropbox, owncloud or bitpocket to name a few. You can imagine I use the latter (if you want a recommendation)¹.

In any case you want to encrypt what you send to be stored in "the cloud" even if it is just for a short time. There are many options how to encrypt the "in flight" data. Symmetric ciphers are probably the safest and most widely researched cryptography these days and easier to use than asymmetric key pairs in this context as well.

Encryption is notoriously hard to implement correctly and worthless when the implementation is flawed. So I looked at gpg, a well known reference implementation, and was amazed that it can neither use a proper keyfile for symmetric encryption (you can just supply a passphrase via --passphrase-file) nor does it handle multiple files on the command line consistently. You can use --multifile (wondering...why does a command need that at all?) with --decrypt and --encrypt (asymmetric public/private key pair encryption) but not with --symmetric (symmetric shared key encryption). Duh!

With a bit of scripting around the gpg shortcomings, you end up with crypt_gpg that can nicely encrypt or decrypt multiple files (symmetric cipher) in one go.