This is not normal. Modern cryptosystems don't have anything like PGP's insane "packet" format, which has caused other problems before this. There's no principal of design that would lead you to what PGP came up with, and the only reason we still have to deal with it is path dependence. I don't even care if you call the next design "PGP2", just throw this system in the bin and start over.
Unfortunately, modern cryptographers refuse to design systems for confidentiality of store-and-forward communications, motivated by the fact that one can provide better security in instant messaging[1] (which in most cases implies vendor lock-in). Age is one of the few systems that could accomodate email, and its author’s “solution”[2] is for the user do ASCII armor/dearmor like a caveman, which handily loses to PGP/MIME in just about every email client that supports the latter. So, until somebody does better, PGP email it is.
I'll admit that my knowledge of signed/encrypted email is mostly from S/MIME (and underlying CMS), so I'm curious if you could enlighten me on what PGP is doing that is so much more insane than that.
Well, I don't know if I would call PGP so much more insane than CMS or PKCS#7 :-). Definitely worse, but CMS is not high up on the list of honorable cryptographic envelope designs.
On the format level, CMS has some of the same flaws as PGP: dynamic TLV encodings (BER), extension points everywhere, and a disconnect between format and cryptographic versioning. On the cryptographic level, S/MIME benefits somewhat from certificates on the Internet PKI being less of a wild west than PGP certificates, and from having a community group (the S/MIME Cert WG of the CA/B Forum) invested in strengthening S/MIME's certificate profile beyond the baseline stipulated in RFC 5280. Of course, for non-public S/MIME deployments, none of that applies.
All that said, I don't think I would treat S/MIME (or CMS, or PKCS#7) as a guiding star: EFAIL affected S/MIME too[1]. But they have the "advantage" of being bad at just their niche (signing and encryption of email), versus being bad at every niche. The latter is PGP's historic curse.
Another year, another critical parsing vulnerability in the PGP ecosystem. Latacora has an excellent post[1] that touches on the excessive complexity of PGP's encoding which, remarkably, probably isn't even in the top 3 things wrong with PGP.
My personal favorite of these is when someone sent a weaponized compression packet to oss-sec in 2022[2].
The complaint about excessive complexity was about the packet length representation. That isn't a really great example. The PGP packet length representation is fairly straightforward.
You've linked this commentary in just about every PGP thread I've seen on HN, but the vulnerabilities keep coming. I don't think a dynamic TLV encoding was defensible a decade ago, and it certainly isn't defensible in 2025.
(As the Latacora post points out, this is the same essential error that cryptographic applications of BER make. The difference is that serious users of ASN.1 have mostly sobered up and switched to DER; no such sobering has happened in the PGP ecosystem.)
You are writing this comment on a story where that packet format literally created a signature bypass vulnerability. Tell us more about how straightforward it is?
Readit News
[1] https://blog.cryptographyengineering.com/2014/08/13/whats-ma...
[2] https://github.com/FiloSottile/age/issues/93
https://www.latacora.com/blog/2020/02/19/stop-using-encrypte...
But none of that excuses PGP's clanking and outmoded design. Things that are bad are bad. We can't moralize our way around that.
On the format level, CMS has some of the same flaws as PGP: dynamic TLV encodings (BER), extension points everywhere, and a disconnect between format and cryptographic versioning. On the cryptographic level, S/MIME benefits somewhat from certificates on the Internet PKI being less of a wild west than PGP certificates, and from having a community group (the S/MIME Cert WG of the CA/B Forum) invested in strengthening S/MIME's certificate profile beyond the baseline stipulated in RFC 5280. Of course, for non-public S/MIME deployments, none of that applies.
All that said, I don't think I would treat S/MIME (or CMS, or PKCS#7) as a guiding star: EFAIL affected S/MIME too[1]. But they have the "advantage" of being bad at just their niche (signing and encryption of email), versus being bad at every niche. The latter is PGP's historic curse.
[1]: https://efail.de/
My personal favorite of these is when someone sent a weaponized compression packet to oss-sec in 2022[2].
[1]: https://www.latacora.com/blog/2019/07/16/the-pgp-problem/
[2]: https://seclists.org/oss-sec/2022/q3/9
* https://articles.59.ca/doku.php?id=pgpfan:tpp
The complaint about excessive complexity was about the packet length representation. That isn't a really great example. The PGP packet length representation is fairly straightforward.
(As the Latacora post points out, this is the same essential error that cryptographic applications of BER make. The difference is that serious users of ASN.1 have mostly sobered up and switched to DER; no such sobering has happened in the PGP ecosystem.)
Dead Comment