Context engineering: Tackling legacy systems with generative AI

Generative AI can be incredibly powerful when it comes to legacy modernization. Not only can it help us better understand a large, aging codebase, it can even help us reverse engineer a legacy system when we don't have access to the complete source code. Doing it, though, requires a specific approach that's being described as 'context engineering'. This is something we've been exploring a lot in recent months at Thoughtworks. On this episode of the Technology Podcast, Thoughtworks' lead for AI-enabled software engineering, Birgitta Böckeler, and tech principal Chandirasekar Thiagarajan join hosts Ken Mugrage and Neal Ford to discuss how it works. They explain the process, the tools and what the work is teaching them about both generative AI and legacy modernization. Read Birgitta's blog post on reverse engineering with AI:

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Context engineering: Tackling legacy systems with generative AI is an episode from ThoughtWorks by Thoughtworks.

This episode is 40:41 long.

This episode was published on Aug 21, 2025.

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