Summary

PyPI is a core component of the Python ecosystem that most developer’s have interacted with as either a producer or a consumer. But have you ever thought deeply about how it is implemented, who designs those interactions, and how it is secured? In this episode Nicole Harris and William Woodruff discuss their recent work to add new security capabilities and improve the overall accessibility and user experience. It is a worthwhile exercise to consider how much effort goes into making sure that we don’t have to think much about this piece of infrastructure that we all rely on.

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• Your host as usual is Tobias Macey and today I’m interviewing Nicole Harris and William Woodruff about the work they are doing on the PyPI service to improve the security and utility of the package repository that we all rely on

Interview

• Introductions
• How did you get introduced to Python?
• Can you start by sharing how you each got involved in working on PyPI?
  • What was the state of the system at the time that you first began working on it?
• Once you committed to working on PyPI how did you each approach the process of identifying and prioritizing the work that needed to be done?
  • What were the most significant issues that you were faced with at the outset?
• How often have the issues that you each focused on overlapped at the cross section of UX and security?
  • How do you balance the tradeoffs that exist at that boundary?
• What is the surface area of the domains that you are each working in? (e.g. web UI, system API, data integrity, platform support, etc.)
  • What are some of the pain points or areas of confusion from a user perspective that you have dealt with in the process of improving the platform?
• What have been the most notable features or improvements that you have each introduced to PyPI?
  • What were the biggest challenges with implementing or integrating those changes?
• How do you approach introducing changes to PyPI given the volume of traffic that it needs to support and the level of importance that it serves in the community?
• What are some examples of attack vectors that exist as a result of the nature of the PyPI platform and what are you most concerned by?
• How does poor accessibility or user experience impact the utility of PyPI and the community members who interact with it?
• What have you found to be the most interesting/challenging/unexpected aspects of working on Warehouse?
  • What are some of the most useful lessons that you have learned in the process?
• What do you have planned for future improvements to the platform?
  • How can the listeners get involved and help out?
• How was this work funded?

Keep In Touch

• Nicole
  • @nlhkabu on Twitter
  • Website
  • If you’re using CI to upload to PyPI and would like to speak with Nicole please book a time here
  • If you’re using assistive technology and would like to speak with Nicole please book a time here
• William
  • @8x5clPW2
  • Website
  • Email
  • Please get in touch if you’d like to work with Trail of Bits on your next security project!

Picks

• Tobias
  • The Expanse TV Series
• Nicole
  • The Great Hack documentary
• William
  • Abraham Lincoln Autobiography by Carl Sandburg

Links

• PyPI
• Warehouse
  • Issue Tracker
  • Good First Issues
• PeopleDoc
• Trail of Bits
• OSQuery
• Django
• Ruby
• Python Software Foundation
  • Python Packaging Working Group
  • Podcast Episode
• Donald Stufft
  • Podcast Episode
• UX (User Experience) Design
• OTF == Open Technology Fund
• Bootstrap
• TOTP
• WebauthN
• Yubikey
• Changeset Consulting
• Sumana Harihareswara
• WCAG (Web Content Accessibility Guidelines) 2.0
• Macaroon Security Tokens
• Docker Compose
• MOSS = Mozilla Open Source Support

The intro and outro music is from Requiem for a Fish The Freak Fandango Orchestra / CC BY-SA