Stop Using Encrypted Email with William Woodruff
Security Cryptography Whatever
Intro
In this chapter, the speakers delve into the topic of PGP encryption, questioning its real-world effectiveness and likening its use to performative behavior. They also touch on a recent vulnerability in Open PGP, prompting a discussion on the nuances and implications of email security.
There was a bug in an OpenPGP library which finally gave us an excuse to tear encrypted email via PGP to shreds. Our special guest William Woodruff joined us to help explain the vuln and indulge our gnashing of teeth on why email was never meant to be encrypted and how other modern tools do the job much, much better.
Watch on YouTube: https://www.youtube.com/watch?v=IoL3LfIozJo
Transcript: https://securitycryptographywhatever.com/2025/08/22/stop-using-encrypted-email-with-william-woodruff
Links:
- William Woodruff: https://yossarian.net/
- https://www.latacora.com/blog/2020/02/19/stop-using-encrypted/
- https://www.rfc-editor.org/rfc/rfc4880
- https://codeanlabs.com/blog/research/cve-2025-47934-spoofing-openpgp-js-signatures/
- https://www.mailpile.is/blog/2014-10-07_Some_Thoughts_on_GnuPG.html
- https://www.rfc-editor.org/rfc/rfc9580.html
- https://www.tumblr.com/accidentallyquadratic
- https://www.w3.org/TR/xmldsig-core/
- https://support.yubico.com/hc/en-us/articles/360013790259-Using-Your-YubiKey-with-OpenPGP
- https://www.rfc-editor.org/rfc/rfc9580.html#name-signature-packet-type-id-2
- https://www.rfc-editor.org/rfc/rfc9580.html#name-key-derivation-function
- https://en.wikipedia.org/wiki/S/MIME
- https://delta.chat
- https://signal.org/blog/the-ecosystem-is-moving/
- https://phakeobj.netlify.app/posts/gigacage/
- https://x.com/dakami
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"Security Cryptography Whatever" is hosted by Deirdre Connolly (@durumcrustulum), Thomas Ptacek (@tqbf), and David Adrian (@davidcadrian)
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