Context Engineering: Building Better Context Systems with DSPy

Context systems often fail in ways that better prompting alone will not fix. In this hands-on workshop with the author of O'Reilly's The Context Engineering Handbook, you’ll diagnose a range of common—and less common—context failures, understand why they occur and implement evidence-based fixes with DSPy.

You’ll build a context-engineering harness that can evaluate performance, expose failures and support iterative improvement. Using compound-AI techniques, you’ll create compaction functions tailored to particular use cases, add security mechanisms for coding agents and build tool-selection functions that reduce context bloat. The emphasis is on developing useful mental models as well as working code.

You’ll leave with a starter repository and a working harness you can continue adapting to your own systems.

Who it’s for

Software and AI engineers who want to build more reliable context systems. Python fluency is helpful, but participants who work in another language and are comfortable using a coding agent should be able to follow. No previous DSPy experience is required.

What you’ll need

Bring a laptop on which you can install and run a local Python development environment. You’ll need GitHub access, uv installed, a coding agent and a model API key from an inference provider. Enterprise-managed laptops that prevent you from creating a Python environment are unlikely to work.

About the presenter

Drew Breunig

Drew Breunig is the CEO and co-founder of Cmpnd, where he works on DSPy and helps teams build reliable AI applications. He is editing The Context Engineering Handbook for O'Reilly Media, and advises the Overture Maps Foundation on its Global Entity Reference System, which makes it easy to join geospatial datasets. Previously he ran strategy, data science and strategic client projects at PlaceIQ (acquired by Precisely), and with Nicholas Felton co-founded Reporter, an award-winning app. He writes about AI, data, geo and culture at dbreunig.com.