Debian has a number of legacy tools (that's a euphemism for ugly hacks) that are not addressed due to inertia, fear of breaking stuff, and the difficulty of reaching consensus for changes with cross-package impact. I'll talk about dealing with the above issues in the context of ongoing work as part of Debian Enhancement Proposal 9. Specifically, the talk will cover how (not) to make proposals for cross-package changes, and how to map behaviour in a technical spec to feature-centered assertions in a test suite.