[BUG] All Checklist Steps Marked as Completed Regardless of Actual Outcome

!Image# Bug Report: All Checklist Steps Marked as Completed Regardless of Actual Outcome

Environment

• Platform (select one):
• [x] Anthropic API
• [ ] AWS Bedrock
• [ ] Google Vertex AI
• [ ] Other:
• Claude CLI version: 1.0.11
• Operating System: Ubuntu 22.04 (via WSL2)
• Terminal: Windows Terminal

Bug Description

When using Claude via the Anthropic API to generate or update multi-step TODO lists or checklists, every step is marked as completed (✅), regardless of whether it actually succeeded or failed. This leads to misleading outputs and undermines the reliability of automated workflows, CI/CD checks, and manual verifications.

Steps to Reproduce

1. Define a checklist with multiple tasks or verification steps.
2. Manually or programmatically execute those steps, including at least one known failure.
3. Allow Claude to update or evaluate the checklist.
4. Observe that all items, including failed or skipped steps, are still marked as ✅ completed.

Expected Behavior

Checklist items should reflect actual outcomes:

• ✅ for successful steps
• ❌, ⚠️, or unchecked for failures or skipped steps

This ensures the checklist accurately represents what was and wasn’t accomplished.

Actual Behavior

Claude marks all checklist steps as ✅, even if some steps were incomplete, failed, or explicitly errored out. This behavior misrepresents the real execution state and can cause incorrect assumptions in development or deployment pipelines.

Additional Context

This issue affects any structured TODO or checklist flow where Claude is asked to interpret or update step status.
Example (redacted for generality):