[BUG] User has to repeat an explicit order three times before it is carried out

Re-filing #97182, which was closed for missing reproduction steps. Steps below are exact.

Environment

• Claude Code: 2.1.280
• Model: claude-opus-5-5[1m]
• OS: macOS 26.6.2
• Instructions loaded: project CLAUDE.md plus auto-memory MEMORY.md (both present in context at session start)

Steps to reproduce

1. Start a Claude Code session in a repo with gh authenticated.
2. Ask: "raise these issues to Anthropic on GitHub" (list several issues).
3. The model first calls an in-product feedback tool that is disabled in the session; the call errors.
4. Clarify: "GitHub issues". The model reads local notes and runs gh auth status / gh repo view before creating anything.
5. The model runs gh issue create; the permission prompt rejects it. The model retries the identical call instead of stating the blocker.
6. The order has to be given a third time before the model explains the blocker.

Actual

The same order has to be repeated three times; each attempt ends in a detour.

Expected

On the first order: file the issues, or immediately state the exact blocker and the single command the user can run.

Raised with Claude Code