Name: Towards AI Legal Name: Towards AI, Inc. Description: Towards AI is the world's leading artificial intelligence (AI) and technology publication. Read by thought-leaders and decision-makers around the world. Phone Number: +1-650-246-9381 Email: pub@towardsai.net
228 Park Avenue South New York, NY 10003 United States
Website: Publisher: https://towardsai.net/#publisher Diversity Policy: https://towardsai.net/about Ethics Policy: https://towardsai.net/about Masthead: https://towardsai.net/about
Name: Towards AI Legal Name: Towards AI, Inc. Description: Towards AI is the world's leading artificial intelligence (AI) and technology publication. Founders: Roberto Iriondo, , Job Title: Co-founder and Advisor Works for: Towards AI, Inc. Follow Roberto: X, LinkedIn, GitHub, Google Scholar, Towards AI Profile, Medium, ML@CMU, FreeCodeCamp, Crunchbase, Bloomberg, Roberto Iriondo, Generative AI Lab, Generative AI Lab VeloxTrend Ultrarix Capital Partners Denis Piffaretti, Job Title: Co-founder Works for: Towards AI, Inc. Louie Peters, Job Title: Co-founder Works for: Towards AI, Inc. Louis-François Bouchard, Job Title: Co-founder Works for: Towards AI, Inc. Cover:
Towards AI Cover
Logo:
Towards AI Logo
Areas Served: Worldwide Alternate Name: Towards AI, Inc. Alternate Name: Towards AI Co. Alternate Name: towards ai Alternate Name: towardsai Alternate Name: towards.ai Alternate Name: tai Alternate Name: toward ai Alternate Name: toward.ai Alternate Name: Towards AI, Inc. Alternate Name: towardsai.net Alternate Name: pub.towardsai.net
5 stars – based on 497 reviews

Frequently Used, Contextual References

TODO: Remember to copy unique IDs whenever it needs used. i.e., URL: 304b2e42315e

Resources

Free: 6-day Agentic AI Engineering Email Guide.
Learnings from Towards AI's hands-on work with real clients.
Claude Code Pitfalls: Claude Code Won’t Do What You Told It: A Troubleshooting Catalog
Latest   Machine Learning

Claude Code Pitfalls: Claude Code Won’t Do What You Told It: A Troubleshooting Catalog

Last Updated on June 3, 2026 by Editorial Team

Author(s): Rick Hightower

Originally published on Towards AI.

Part 17: Why your config looks right but Claude ignores it, and the exact commands that diagnose it in seconds

In this article: Most Claude Code failures are not mysteries. They are a small set of recurring patterns: files that load on demand instead of at startup, permission rules that quietly override your mode, descriptions that fail to trigger a subagent. This is a Claude Code troubleshooting catalog grouped into five categories, with the exact diagnostic commands for each. Read it once and you will spend dramatically less time chasing configuration ghosts.

Claude Code Pitfalls: Claude Code Won’t Do What You Told It: A Troubleshooting Catalog

Claude Code Troubleshooting

After the introduction, the article lays out a practical troubleshooting catalog for Claude Code. It begins with four “muscle memory” commands (/doctor, /context, /memory, and /debug) that resolve most issues quickly, then explains five recurring categories of failure: loading problems (often caused by on-demand CLAUDE.md loading rather than startup), permission surprises (ask/allow rules override mode settings), delegation not triggering (subagent/skill descriptions must be specific and trigger-based), integrations going quiet (use /mcp, /hooks, and correct project-scoped configuration; debug failures including auth, paths, and permissions), and environment quirks (UI/input changes, trust/worktree behavior, and performance issues traced to state). It closes with a diagnostic order to follow when you’re stuck, the scope/precedence rule behind “it should work” situations, and a “do this today” checklist to build the instinct for diagnosing problems in seconds.

Read the full blog for free on Medium.

Join thousands of data leaders on the AI newsletter. Join over 80,000 subscribers and keep up to date with the latest developments in AI. From research to projects and ideas. If you are building an AI startup, an AI-related product, or a service, we invite you to consider becoming a sponsor.

Published via Towards AI


Towards AI Academy

We Build Enterprise-Grade AI. We'll Teach You to Master It Too.

15 engineers. 100,000+ students. Towards AI Academy teaches what actually survives production.

Start free — no commitment:

6-Day Agentic AI Engineering Email Guide — one practical lesson per day

Agents Architecture Cheatsheet — 3 years of architecture decisions in 6 pages

Our courses:

AI Engineering Certification — 90+ lessons from project selection to deployed product. The most comprehensive practical LLM course out there.

Agent Engineering Course — Hands on with production agent architectures, memory, routing, and eval frameworks — built from real enterprise engagements.

AI for Work — Understand, evaluate, and apply AI for complex work tasks.

Note: Article content contains the views of the contributing authors and not Towards AI.