Security Cryptography Whatever

The Python cryptography module, pyca/cryptography, has mostly been a sane wrapper around a pile of C, so that users get performant cryptography on the many, many platforms Python targets. Therefore its maintainers, Alex Gaynor and Paul Kehrer, have become intimately familiar with OpenSSL. Recently, they declared that after many years of trying to make it work, they announced pyca/cryptography would be moving away from OpenSSL when supporting new functionality and exploring adding other backends instead. We invited them on to tell us about what has happened to OpenSSL, even after the investments and improvements following Heartbleed. No guests on this pod represent anyone besides themselves.
Watch on YouTube: https://www.youtube.com/watch?v=dEKBHI3rodY

Transcript: https://securitycryptographywhatever.com/2026/02/01/python-cryptography-breaks-up-with-openssl

Links:
- https://cryptography.io/en/latest/statements/state-of-openssl/
- Py Cryptography: https://cryptography.io
- https://archive.openssl-conference.org/2025/presentations/Alex_Gaynor_Paul_Kehrer_The_Python_Cryptographic_Authoritys_OpenSSL_Experience.pdf
- https://securitycryptographywhatever.com/2025/08/16/alex-gaynor/
- https://packages.gentoo.org/packages/media-libs/libsdl
- https://www.youtube.com/watch?v=RUIguklWwx0
- https://datatracker.ietf.org/doc/rfc9180/
- https://docs.openssl.org/3.3/man3/OSSL_PARAM/
- https://openssl.foundation/
- https://github.com/openssl/openssl/issues/17064
- https://www.feistyduck.com/newsletter/issue_132_openssl_performance_still_under_scrutiny
- https://github.com/topazproject/topaz
- https://github.com/actions/runner/issues/1069
- https://crystalhotsauce.com/
- https://openssl-library.org/news/vulnerabilities/#CVE-2025-15467
- https://en.wikipedia.org/wiki/Ship_of_Theseus
- https://boringssl.googlesource.com/boringssl/+/aa202db1d7091b88b80f0a58c630c5c1aefc817d
- https://www.ibm.com/products/open-sdk-for-rust-aix
- https://dadrian.io/blog/posts/corporate-support-xz/
- https://peps.python.org/
- https://cryptography.io/en/latest/hazmat/primitives/asymmetric/ed448/
- https://go.dev/blog/fips140
- https://dadrian.io/blog/posts/roll-your-own-crypto/

"Security Cryptography Whatever" is hosted by Deirdre Connolly (@durumcrustulum), Thomas Ptacek (@tqbf), and David Adrian (@davidcadrian)

The International Association of Cryptologic Research held their regular election using secure voting software called Helios…and lost the keys to decrypt the results, leaving them with no choice but to throw out the vote and call a new election. Hilarity ensues. We welcome special guest Matt Bernhard who actually works on secure voting systems to explain which bits are homomorphically additive or not.

Watch on YouTube: https://www.youtube.com/watch?v=euw_yqAQFI8

Transcript: https://securitycryptographywhatever.com/2025/12/30/iacr-helios

Links:
- NYT: https://www.nytimes.com/2025/11/21/world/cryptography-group-lost-election-results.html
- IACR Memo: https://www.iacr.org/news/item/27138
- https://www.iacr.org/elections/
- https://vote.heliosvoting.org/faq
- https://github.com/Election-Tech-Initiative/electionguard
- https://www.usenix.org/legacy/events/sec08/tech/full_papers/adida/adida.pdf
- https://www.iacr.org/elections/eVoting/about-helios.html
- https://www.iacr.org/elections/eVoting/
- https://crypto.ethz.ch/publications/files/CrGeSc97b.pdf
- https://electionguard.vote/
- https://eprint.iacr.org/2025/1901
- https://freeandfair.us/blog/open-free-election-technology/
- https://www.starvoting.org/
- https://mbernhard.com/

"Security Cryptography Whatever" is hosted by Deirdre Connolly (@durumcrustulum), Thomas Ptacek (@tqbf), and David Adrian (@davidcadrian)

Apple announced its new suite of memory security improvements from the top of the stack all the way to the bottom, so we dug through what they did and how they did it (performantly). 

Watch on YouTube: https://www.youtube.com/watch?v=9FJwOI2PliU

Transcript: https://securitycryptographywhatever.com/2025/10/31/apple-mie

Links:

- https://security.apple.com/blog/memory-integrity-enforcement/
- Secure Page Table Monitor and Trusted Execution Monitor: https://support.apple.com/guide/security/operating-system-integrity-sec8b776536b/1/web/1#secd022396fb
- https://security.apple.com/blog/towards-the-next-generation-of-xnu-memory-safety/
- https://developer.apple.com/documentation/xcode/adopting-type-aware-memory-allocation
- https://security.apple.com/blog/what-if-we-had-sockpuppet-in-ios16/
- https://arxiv.org/pdf/2510.09272
- https://googleprojectzero.blogspot.com/2023/11/first-handset-with-mte-on-market.html
- https://developer.apple.com/documentation/xcode/adopting-type-aware-memory-allocation
- https://arxiv.org/pdf/2510.09272
- https://spectreattack.com/spectre.pdf

"Security Cryptography Whatever" is hosted by Deirdre Connolly (@durumcrustulum), Thomas Ptacek (@tqbf), and David Adrian (@davidcadrian)

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)

We chat with friend of the pod and special guest Alex Gaynor, former deputy chief technologist at the FTC and all around good Security Person™. Join for nerdery about WebAuthn, stay for accidentally melting down GitHub APIs around November 2020! 
Watch on YouTube: https://www.youtube.com/watch?v=gBoGvyvsSi4
Transcript: https://securitycryptographywhatever.com/2025/08/16/alex-gaynor
Links:
- https://knowyourmeme.com/memes/no-take-only-throw
- https://alexgaynor.net/2025/jan/13/challenges-funding-open-source/
- https://alexgaynor.net/2025/apr/08/putting-a-price-tag-on-open-source/
- https://dadrian.io/blog/posts/corporate-support-xz/
- https://alex.github.io/nyt-2020-election-scraper/battleground-state-changes.html
- https://github.com/alex/nyt-2020-election-scraper

"Security Cryptography Whatever" is hosted by Deirdre Connolly (@durumcrustulum), Thomas Ptacek (@tqbf), and David Adrian (@davidcadrian)