(Edit: BTW, if you haven't, read Nudge by Thaler and Sunstein. It's a somewhat long-winded exploration on choice architectures, but you're neck deep in that space now. I'll give you my copy if you're in SF.)

Thanks for the openness. I got bit by this one and was, frankly, pretty surprised.

The funny thing about user-facing interaction mechanics is that everyone is part of some minority, and everyone comes with their own sense of what "natural" or "obvious" is. With something this impactful, communicated clarity of behavior will important. Your feature is also doing double-duty, serving as a last net against prompt-injection attacks by giving the user the final say.

(Also, BTW, folks outside of Anthropic are unlikely to be as tooled-up for long-running unsupervised Claude jaunts as you guys. The cost of wild success is wide adoption.)

One thing I'll suggest is that the mechanics of permissions and asking are presently pretty hacker/nerd friendly but simultaneously too-scary and not-scary-enough for non-coders.

Examples:

- Wild-cards on always approve is awesome, but, with prefixes like timeout and nohup, the "thing" that is getting done is buried and largely unexplained to the user.

- Auto is actually kind of a sweet spot (sometimes goes off into the weeds), but the designers and PM's I've been working with might as well YOLO. They have no idea if they're breaking things, but they gravitate between plan and auto mode.

- Fewer permission prompts is great, but it comes after a user has slogged through generation of a data-set to work against, like battle scars for paper cuts. It's the thermostat problem. The signal comes when the user is uncomfortable. And it's a way to learn me, but not me now.

I've had good fortune with Opus 4.8 and Fable just telling the system what phase of my life it's in. Things like "I'm going to go make dinner... Go profile the matrix or configurations and build the dataset for the next two hours while I'm away" have a pretty good hit rate. On the flip side "keep me in the loop and bring me your results before making structural changes" also articulates well with Fable. It will tread more carefully.

And these approaches are the ones we'd use with someone transitioning from SDE1 to SDE2. A little more autonomy, and the grounding in the bigger picture. Can we eventually translate to perfectly judging what the user wants in the moment based on incomplete signal?

No, but I'm glad you're trying. Keep the interaction model clear to your broad set of users, and we'll come along for the ride.