The Gray Area with Sean Illing The Great Enshittening
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Oct 20, 2025 
Cory Doctorow, a journalist and science fiction author known for his work on digital rights, dives deep into the concept of enshittification—the decline of online platforms. He unpacks how this decay happens, starting with Google's 2019 changes and extending to how other industries are affected. Doctorow discusses the reasons users stick with subpar platforms, the implications of monopolies, and the importance of potential reforms in policy and collective action. He poses an intriguing question: can we ever reverse this trend?
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Facebook Bought Instagram To Keep Users
- Doctorow recounts Facebook buying Instagram to retain users who preferred Instagram over Facebook.
- He notes Zuckerberg wrote "better to buy than to compete," showing deliberate consolidation strategy.
Laws That Lock Down Devices
- The 1998 anti-circumvention law (stemming from WIPO treaties) criminalizes reverse engineering even for lawful purposes.
- This global legal regime prevents competitors and users from unlocking digital devices and building alternative marketplaces.
Enshittification Goes Offline
- Enshittification will spread beyond apps as physical retail and services digitize and adopt remote pricing controls.
- Digital shelf tags and dynamic pricing let firms "twiddle" in the real world, enabling higher prices and worse service.
