[FEATURE] Show which installed skills and connectors fit a prompt, and let the user choose

Preflight Checklist

• [x] I have searched existing requests and this feature hasn't been requested yet
• [x] This is a single feature request (not multiple features)

Problem Statement

With many skills, plugins and connectors installed, Claude Code chooses which ones to use silently. I have about 130 skills and 12 connectors, and for a given prompt I can't tell which ones were considered, which was chosen, or whether a better-suited one was skipped. I often only learn a relevant skill existed after the task is done.

Proposed Solution

At the start of a task, optionally show a short list of the installed skills and connectors that fit the prompt, each with a one-line reason, and let the user select which to use. It should be skippable, off by default or easy to turn off, and silent when nothing fits.

Alternative Solutions

I built this as a plugin using a UserPromptSubmit hook that injects an instruction on the first prompt of a session. It works, but a hook can only ask the model to do this; it can't see account-level connectors or built-in skills on disk, and it costs extra context.

Priority

Medium - Would be very helpful

Feature Category

Interactive mode (TUI)

Use Case Example

I type "anything blowing up in prod since last night?". Claude Code shows Vercel, Supabase, Sentry and PostHog with a reason for each. I tick Vercel and Sentry, and it proceeds with those.

Additional Context

Working prototype: https://github.com/Shrey-Parikh31/tool-picker