I haven’t tested with Claude specifically in a while, but I see this a lot on larger features.

It tends to be small decisions way down the stack that bubble up, or an incoherent data model that can’t handle what you’re asking for cleanly.

Eg I was messing with a state tracker the other day. The state tracker assumes a container is either currently running, or fully removed from disk.

The LLM chose to remove the state file when the container is stopped and then to remove it after, which leaks container storage.

The LLM is kind of stuck though, because every option other than “rewrite the data model” has negative outcomes and it probably violates user expectations to launch a massive rewrite there.

I've found Opus 5.5 is quite good at surfacing and clarifying these issues using Grilling[0]. Often I find that I want to expand the scope of work much larger than Claude would consider based on my original request.

0. https://github.com/mattpocock/skills/blob/main/skills/produc...