Stop Using Encrypted Email with William Woodruff
Security Cryptography Whatever
Critique of Encrypted Email Practices
This chapter delves into the complexities of the V8 sandbox and memory addressing while reflecting on cybersecurity insights. The speakers also critique the use of encrypted email and conclude with a light discussion on their podcast and guest appreciation.
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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