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

-----BEGIN PGP MESSAGE-----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-----END PGP MESSAGE-----

"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)

We’re throwing a party in Vegas! Someone called it SCWPodCon last year, and the name stuck. It’s sponsored by Teleport, the infrastructure identity company. Get SSO for SSH! If Thomas was here, I’m sure he’d tell you that Fly.io uses Teleport internally. Oh also there's some thing called Black..pill? Black Pool? Something like that happening in Vegas, with crypto talks, so we chatted about them a bit, plus some other stuff

SCWPodCon 2025: https://securitycryptographywhatever.com/events/blackhat

Transcript: https://securitycryptographywhatever.com/2025/07/29/vegas-baby/

Links:

- Fault Injection attacks on PQCS signatures: https://www.blackhat.com/us-25/briefings/schedule/index.html#bypassing-pqc-signature-verification-with-fault-injection-dilithium-xmss-sphincs-46362
- Another attack on TETRA: https://www.blackhat.com/us-25/briefings/schedule/index.html#2-cops-2-broadcasting-tetra-end-to-end-under-scrutiny-46143
- Attacks on SCADA / ICS protocols (OPC UA): https://www.blackhat.com/us-25/briefings/schedule/index.html#no-vpn-needed-cryptographic-attacks-against-the-opc-ua-protocol-44760
- Attacks on Nostr: https://www.blackhat.com/us-25/briefings/schedule/index.html#not-sealed-practical-attacks-on-nostr-a-decentralized-censorship-resistant-protocol-45726
- https://signal.org/blog/the-ecosystem-is-moving/
- https://en.wikipedia.org/wiki/Nostr
- https://eurosp2025.ieee-security.org/program.html
- https://cispa.de/en/research/publications/84648-attacking-and-fixing-the-android-protected-confirmation-protocol
- https://hal.science/hal-05038009v2/file/main.pdf
- 8-bit, abacus, and a dog: https://eprint.iacr.org/2025/1237.pdf
- https://www.youtube.com/watch?v=Dlsa9EBKDGI
- https://www.quantamagazine.org/computer-scientists-figure-out-how-to-prove-lies-20250709/
- https://eprint.iacr.org/2025/118

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

It seems like everyone that tries to deploy end-to-end encrypted cloud
storage seems to mess it up, often in new and creative ways. Our special
guests Matilda Backendal, Jonas Hofmann, and Kien Tuong Truong give us a tour through the breakage and discuss a new formal model of how to actually build a secure E2EE storage system.

Watch on YouTube: https://youtu.be/sizLiK_byCw

Transcript: https://securitycryptographywhatever.com/2025/05/19/e2ee-storage/

Links:

- https://brokencloudstorage.info

- https://eprint.iacr.org/2024/1616.pdf

- https://www.sync.com

- https://www.pcloud.com

- https://icedrive.net

- https://seafile.com

- https://tresorit.com

- https://eprint.iacr.org/2024/989.pdf

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

Migrating the US government to quantum-resistant cryptography is hard, luckily the gamer presidents are on it. This episode is extremely not safe for work, nor does it reflect the political opinions of, well, anybody.

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

Apple has pulled the availability of their opt-in iCloud end-to-end encryption feature, called Advanced Data Protection, in the UK. This doesn't only affect UK Apple users, however.

To help us make sense of this surprising move from the fruit company, we got Matt Green, Associate Professor at Johns Hopkins, and Joe Hall, Distinguished Technologist at the Internet Society, on the horn.

Recorded Saturday February 22nd, 2025.

Transcript: https://securitycryptographywhatever.com/2025/02/24/apple-pulls-adp-in-uk/

Watch episode on YouTube: https://youtu.be/LAn_yOGUkR0

Links:

- https://www.lawfaremedia.org/article/apples-cloud-key-vault-and-secure-law-enforcement-access
- https://www.androidcentral.com/how-googles-backup-encryption-works-good-bad-and-ugly
- https://gdpr.eu/right-to-be-forgotten/
- https://www.legislation.gov.uk/id/ukpga/2024/9
- https://www.nytimes.com/2021/05/17/technology/apple-china-censorship-data.html
- https://en.wikipedia.org/wiki/Salt_Typhoon
- Salt Typhoon: https://www.cisa.gov/news-events/news/strengthening-americas-resilience-against-prc-cyber-threats
- https://www.bloomberg.com/news/articles/2025-02-21/apple-removes-end-to-end-encryption-feature-from-uk-after-backdoor-order
- https://support.apple.com/en-us/102651

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

'Let us model our large language model as a hash function—'

Sold.

Our special guest Nicholas Carlini joins us to discuss differential cryptanalysis on LLMs and other attacks, just as the ones that made OpenAI turn off some features, hehehehe.

Watch episode on YouTube: https://youtu.be/vZ64xPI2Rc0

Transcript: https://securitycryptographywhatever.com/2025/01/28/cryptanalyzing-llms-with-nicholas-carlini/

Links:

- https://nicholas.carlini.com
- “Stealing Part of a Production Language Model”: https://arxiv.org/pdf/2403.06634
- ‘Why I attack"’: https://nicholas.carlini.com/writing/2024/why-i-attack.html
- “Cryptanalytic Extraction of Neural Network Models”, CRYPTO 2020: https://arxiv.org/abs/2003.04884
- “Stochastic Parrots”: https://dl.acm.org/doi/10.1145/3442188.3445922
- https://help.openai.com/en/articles/5247780-using-logit-bias-to-alter-token-probability-with-the-openai-api
- https://community.openai.com/t/temperature-top-p-and-top-k-for-chatbot-responses/295542
- https://opensource.org/license/mit
- https://github.com/madler/zlib
- https://ai.meta.com/blog/yann-lecun-ai-model-i-jepa/
- https://nicholas.carlini.com/writing/2024/how-i-use-ai.html

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

Just a few days before turning off the lights, the Biden administration dropped a huge cybersecurity executive order including a lot of good stuff, that hopefully [cross your fingers, knock wood, spin around three times and spit] will last into future administrations. We snagged some time with Carole House, outgoing Special Advisor and Acting Senior Director for Cybersecurity and Critical Infrastructure Policy, National Security Council in the Biden-Harris White House, to give us a brain dump.

And now due to popular demand, with video of our actual human¹ faces! https://youtu.be/Pqw0W2crQiM

Transcript: https://securitycryptographywhatever.com/2025/01/20/bidens-cyber-everything-bagel-carole-house/

Links:
- https://www.federalregister.gov/d/2025-01470
- https://www.wired.com/story/biden-executive-order-cybersecurity-ai-and-more/
- 2022 EO: https://archive.ph/hvzWd
- 2023 EO: https://www.whitehouse.gov/wp-content/uploads/2023/06/M-23-16-Update-to-M-22-18-Enhancing-Software-Security-1.pdf
- 2021 EO: https://www.federalregister.gov/documents/2021/05/17/2021-10460/improving-the-nations-cybersecurity
- NIST SSDF: https://nvlpubs.nist.gov/nistpubs/SpecialPublications/NIST.SP.800-218.pdf
- https://www.federalregister.gov/documents/2015/04/02/2015-07788/blocking-the-property-of-certain-persons-engaging-in-significant-malicious-cyber-enabled-activities
- IEEPA: https://www.govinfo.gov/content/pkg/USCODE-2023-title50/pdf/USCODE-2023-title50-chap35-sec1701.pdf

¹ Actual human faces not guaranteed in all cases

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