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Thomas Ptacek

Deirdre Connolly

David Adrian

Some cryptography & security people talk about security, cryptography, and whatever else is happening.

Security Cryptography Whatever

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)

Stop Using Encrypted Email with William Woodruff

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)

Alex Gaynor

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)

Vegas, Baby!

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)

E2EE Storage Done Right with Matilda Backendal Jonas Hofmann and Kien Tuong Truong

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)

Picking Quantum Resistant Algorithms

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)

Apple Pulls Advanced Data Protection in the UK with Matt Green and Joe Hall

'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)

Cryptanalyzing LLMs with Nicholas Carlini

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)

Biden’s Cyber-Everything Bagel with Carole House

THE QUANTUM COMPUTERS ARE COMING...right? We got Samuel Jacques and John Schanck at short notice to answer that question plus a bunch of other about error correcting codes, logical qubits, T-gates, and more about Google's new quantum computer Willow.

Transcript: https://securitycryptographywhatever.com/2024/12/18/quantum-willow

Links:

- https://blog.google/technology/research/google-willow-quantum-chip/ 
- https://research.google/blog/making-quantum-error-correction-work/
- https://blog.google/technology/google-deepmind/alphaqubit-quantum-error-correction/ 
- https://www.nature.com/articles/s41586-024-08449-y
- Sam’s ‘Landscape of Quantum Computing’ chart: https://sam-jaques.appspot.com/quantum\_landscape\_2024 
- The above, originally published in 2021: https://sam-jaques.appspot.com/quantum\_landscape
- https://sam-jaques.appspot.com
- https://jmschanck.info/

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

Quantum Willow with John Schanck and Samuel Jacques

Nothing we have ever recorded on SCW has brought so much joy to
David. However, at several points during the episode, we may have witnessed Matthew Green's soul leave his body.

Our esteemed guests Justin Schuh and Matt Green joined us to debate whether `Dual_EC_DRBG` was intentionally backdoored by the NSA or 'just' a major fuckup.

Transcript: https://securitycryptographywhatever.com/2024/12/07/dual-ec-drbg

Links:

- Dicky George at InfiltrateCon 2014, 'Life at Both Ends of the Barrel - An NSA Targeting Retrospective': [https://youtu.be/qq-LCyRp6bU?si=MyTBKomkIVaxSy1Q](https://youtu.be/qq-LCyRp6bU?si=MyTBKomkIVaxSy1Q)
- Dicky George: [https://www.nsa.gov/Press-Room/Digital-Media-Center/Biographies/Biography-View-Page/Article/3330261/richard-dickie-george/](https://www.nsa.gov/Press-Room/Digital-Media-Center/Biographies/Biography-View-Page/Article/3330261/richard-dickie-george/)
- NYTimes on Sigint Enabling Project: [https://archive.nytimes.com/www.nytimes.com/interactive/2013/09/05/us/documents-reveal-nsa-campaign-against-encryption.html](https://archive.nytimes.com/www.nytimes.com/interactive/2013/09/05/us/documents-reveal-nsa-campaign-against-encryption.html)
- On the Practical Exploitability of Dual EC
in TLS Implementations: [https://www.usenix.org/system/files/conference/usenixsecurity14/sec14-paper-checkoway.pdf](https://www.usenix.org/system/files/conference/usenixsecurity14/sec14-paper-checkoway.pdf)
- Wired - Researchers Solve Juniper Backdoor Mystery; Signs Point to NSA [https://www.wired.com/2015/12/researchers-solve-the-juniper-mystery-and-they-say-its-partially-the-nsas-fault/](https://www.wired.com/2015/12/researchers-solve-the-juniper-mystery-and-they-say-its-partially-the-nsas-fault/)
- ProPublica - Revealed: The NSA's Secret Campaign to Crack, Undermine Internet Security [https://www.propublica.org/article/the-nsas-secret-campaign-to-crack-undermine-internet-encryption](https://www.propublica.org/article/the-nsas-secret-campaign-to-crack-undermine-internet-encryption)
- DDoSecrets - Sigint Enabling Project: [https://data.ddosecrets.com/Snowden%20archive/sigint-enabling-project.pdf](https://data.ddosecrets.com/Snowden%20archive/sigint-enabling-project.pdf)
- IAD: [https://www.iad.gov/](https://www.iad.gov/)
- Ars Technica - “Unauthorized code” in Juniper firewalls decrypts encrypted VPN traffic: [https://web.archive.org/web/20151222023311/http://arstechnica.com/security/2015/12/unauthorized-code-in-juniper-firewalls-decrypts-encrypted-vpn-traffic/](https://web.archive.org/web/20151222023311/http://arstechnica.com/security/2015/12/unauthorized-code-in-juniper-firewalls-decrypts-encrypted-vpn-traffic/)
- 2015 IMPORTANT JUNIPER SECURITY ANNOUNCEMENT: [https://web.archive.org/web/20151221171526/http://forums.juniper.net/t5/Security-Incident-Response/Important-Announcement-about-ScreenOS/ba-p/285554](https://web.archive.org/web/20151221171526/http://forums.juniper.net/t5/Security-Incident-Response/Important-Announcement-about-ScreenOS/ba-p/285554)
- Extended Random Values for TLS: [https://datatracker.ietf.org/doc/html/draft-rescorla-tls-extended-random-00](https://datatracker.ietf.org/doc/html/draft-rescorla-tls-extended-random-00)
- The Art of Software Security Assessment: [https://www.amazon.com/Art-Software-Security-Assessment-Vulnerabilities/dp/0321444426](https://www.amazon.com/Art-Software-Security-Assessment-Vulnerabilities/dp/0321444426)

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

Dual_EC_DRBG with Justin Schuh and Matthew Green

We talk to Kevin Riggle (@kevinriggle) about complexity and safety. We also talk about the Twitter acquisition. While recording, we discovered a new failure mode where Kevin couldn't hear Thomas, but David and Deirdre could, so there's not much Thomas this episode. If you ever need to get Thomas to voluntarily stop talking, simply mute him to half the audience!

https://twitter.com/kevinriggle

Transcript: 
https://securitycryptographywhatever.com/2022/11/24/software-safety-and-twitter-with-kevin-riggle/

Errata

 • It was the Mars Climate Orbiter that crashed due to a units mismatch
 • David confused the Dreamliner with the 737 Max

Links

https://free-dissociation.com/blog/posts/2018/08/why-is-it-so-hard-to-build-safe-software/https://complexsystems.group/https://how.complexsystems.fail/https://noncombatant.org/2016/06/20/get-into-security-engineering/https://blog.nelhage.com/2010/03/security-doesnt-respect-abstraction/http://sunnyday.mit.edu/safer-world.pdfhttps://www.adaptivecapacitylabs.com/john-allspaw/https://www.etsy.com/codeascraft/blameless-postmortemshttps://increment.com/security/approachable-threat-modeling/https://www.nytimes.com/2022/11/17/arts/music/taylor-swift-tickets-ticketmaster.htmlhttps://www.hillelwayne.com/post/are-we-really-engineers/https://www.hillelwayne.com/post/we-are-not-special/https://www.hillelwayne.com/post/what-we-can-learn/https://lotr.fandom.com/wiki/Denethor_IIhttps://twitter.com/sarahjeong/status/1587597972136546304

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

Software Safety and Twitter with Kevin Riggle

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