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How to troubleshoot Claude skills that do not run as expected

A symptom-first guide to Claude Skills failures: check Claude.ai permissions and code execution, validate Claude Code’s exact SKILL.md and YAML frontmatter, test matching and slash commands, then diagnose installation and corporate network problems.
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Start by identifying where the skill is failing: Claude.ai and Claude Code use different controls and file checks. In Claude.ai, a missing or greyed-out Skills area usually points to code-execution or organization permissions. In Claude Code, the usual causes are an incorrectly named SKILL.md, invalid YAML frontmatter, or a description that does not match the request. Use the branch below that matches your environment, then test the skill again after each change.

First, classify the symptom and environment

Do not begin by rewriting the skill. A permission problem, a metadata parsing error, and an automatic-trigger mismatch look similar from the chat window but require different fixes.

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Environment Symptom Most likely control point Evidence that the fix worked
Claude.ai Skills section is missing or skills are greyed out Code execution, account settings, or organization policy The Skills controls are visible and enabled
Claude.ai A skill is enabled but Claude does not use it Toggle state, description, instructions, or request wording Claude selects the skill for a clearly matching request
Claude Code Upload or load fails Skill directory, exact filename, or YAML frontmatter The skill appears in the available-skills list without a parse error
Claude Code Automatic matching fails Name and description metadata, or invocation permissions A matching request triggers it, or a direct slash command works
Claude Code Several commands or sessions fail Installation, version, proxy, or firewall configuration claude doctor or verbose output identifies an environmental issue

Keep the test request simple while troubleshooting. Ask for one task that the skill clearly covers, rather than combining several unrelated jobs. Record whether the skill is visible, enabled, listed, automatically selected, and directly invocable; each result narrows the cause.

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Claude.ai: fix missing or greyed-out Skills

Check code execution first

Claude.ai Skills depend on the code execution environment. If that environment is disabled for your user or workspace, the Skills section may be absent or controls may be unavailable even when the skill package itself is valid. Open the relevant account or organization settings and verify that code execution is allowed, then return to Customize > Skills.

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On Team and Enterprise accounts, an administrator can disable skills or skill creation through organization policy. A custom role may also lack permission to create skills. An owner-provisioned skill can still be usable by a member even when that member cannot create or upload one. Ask an organization owner to confirm the policy and your role before changing the skill text.

Distinguish a policy restriction from a broken skill

  • Missing section for everyone in the workspace: suspect organization policy or a disabled code-execution environment.
  • Missing section only for one user: check that user’s role and individual settings.
  • Section visible but controls greyed out: confirm code execution and whether the administrator allows skill creation or editing.
  • One provisioned skill unavailable while others work: ask the owner to verify that the skill is assigned to your workspace or role.

These checks establish access before you spend time editing instructions. If the controls become available after an administrator change, reload Claude.ai and open Customize > Skills again to confirm the new state.

Claude.ai: when Claude does not select an enabled skill

Confirm the toggle and read the matching text

  1. Open Customize > Skills.
  2. Confirm the intended skill is toggled on for the current account or workspace.
  3. Read its description and instructions as if you were deciding whether a user request matches them.
  4. Submit a focused request that names the task the skill is designed to perform. If appropriate, explicitly mention the skill by name.

Claude uses the skill’s description to decide whether it applies. A vague description such as “helps with documents” gives the matcher little to distinguish from general assistance. State both the action and the situation in which it should run: for example, that the skill converts a supplied spreadsheet into a validated budget report when the user asks for that conversion. Use phrases people actually type, including the file type, output, and important constraints.

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Separate a trigger problem from an instruction problem

Test with a request that unambiguously matches the description. If Claude selects the skill but produces an incorrect result, the trigger is working and the instructions need revision. If Claude never selects it, improve the description and make the request more explicit before changing the procedure itself. Test one wording change at a time so you know which change affected selection.

When a skill is selected intermittently, look for overlap with other enabled skills. Temporarily disable unrelated skills, run the same focused request, and then re-enable them one by one. This is a diagnostic isolation step, not a requirement that users permanently disable useful skills.

Claude Code: verify the skill’s directory and required file

Use the exact filename

Anthropic’s Skills guidance identifies a missing or incorrectly cased SKILL.md as a common upload problem. The file must be named exactly SKILL.md, including capital letters, and must be inside the skill directory Claude Code is scanning. Names such as Skill.md, skill.md, or a file nested in an unexpected subdirectory can prevent loading.

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Keep the directory name simple. The guide illustrates a lowercase, hyphenated skill name; avoid spaces, capitals, and punctuation that the loader may reject. A predictable layout makes inspection easier:

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my-skill/
  SKILL.md

Validate YAML frontmatter before the instructions

The metadata at the top of SKILL.md must have valid YAML delimiters and syntax. A minimal pattern is:

---
name: my-skill
description: Converts a supplied CSV into a checked summary when the user asks for that report.
---

# Instructions

Describe the steps Claude should follow.

Make sure the opening and closing --- lines are present, keys are spelled correctly, and indentation is consistent. A colon, quote, or multiline value that is not valid YAML can stop the skill from loading before Claude ever sees the body. If you recently edited the file, revert to the last known-valid version and add changes incrementally.

Check that the skill is in the location Claude Code scans

Confirm that you are validating the same skills directory used by the current Claude Code installation. A correctly formatted file in an unscanned folder behaves exactly like a missing skill. If the skill came from a plugin, inspect the plugin’s skills directory rather than a separate working copy.

Claude Code: improve automatic matching and invocation

Write a description that answers “what” and “when”

Claude Code uses the skill name and description to match a request, loading the main instructions only after a match. The description should therefore identify the capability and the trigger context. Include the terms users use for the input, operation, and expected output. Replace “handles data” with a concrete statement such as “cleans a user-provided JSON export and produces a deduplicated table when the user asks to normalize records.”

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Do not put the entire procedure in the description. Keep operational detail in the body, while the description supplies enough signal for matching. Avoid promising actions the skill cannot perform; an inaccurate description creates false triggers as well as missed ones.

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Ask Claude Code what it can see

Ask Claude Code to list the available skills. If the skill is absent, return to the directory, filename, frontmatter, and installation checks. If it is listed, submit a request that mirrors the description’s wording. This distinguishes discovery from matching: a listed skill is loaded, while a nonmatching request simply does not activate it.

Use a direct slash command when the skill permits it

If the skill is user-invocable, try its slash command directly, using the documented name, for example:

/skill-name

A successful direct invocation with failed automatic selection indicates a description or prompt-matching issue. A failed direct invocation points instead to availability, naming, permissions, or parsing. Do not infer that every skill supports slash commands; use this test only when the skill is configured as user-invocable.

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Validate plugin skills

When the skill is delivered through a plugin, run the validator against the relevant skills directory:

claude plugin validate

Use the command in the plugin’s documented directory and read the complete error output. Validation can expose packaging or metadata problems that are easy to miss in a chat session.

Installation and session diagnostics in Claude Code

Run the general health check

claude doctor checks the broader Claude Code installation, including installation type and version. It is not a guaranteed skill-specific detector, but it can reveal a broken or unexpected installation that explains why multiple skills fail.

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Capture verbose session output

When the normal transcript does not show why a skill was skipped or a command failed, repeat the operation with Claude Code’s --verbose mode. Verbose output provides turn-by-turn session detail that can show whether the skill was discovered, considered for matching, invoked, or blocked by another error. Treat it as diagnostic evidence rather than proof that the skill instructions are correct.

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Check current setup requirements

Setup requirements change, so verify the live official setup page for the version you are installing. The setup information reviewed for this guide listed macOS 10.15 or later, Ubuntu 20.04 or later, Debian 10 or later, or Windows 10 or later with WSL or Git for Windows; at least 4 GB of RAM; Node.js 18 or later; and internet access. Your current installer may have different requirements.

Anthropic describes global npm, local, and native-binary installation options and advises against sudo npm install -g because it can create permission problems and security risks. If claude doctor reports a path or permission conflict, use the installation method recommended for your operating system instead of forcing a global install with elevated privileges.

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Corporate proxy and firewall failures

If skills work on an unrestricted connection but fail on a company network, investigate transport configuration before editing the skill. Check the HTTP and HTTPS proxy environment variables required by your organization and compare the values with Anthropic’s current Claude Code proxy documentation. Claude Code does not support SOCKS proxies or NO_PROXY; configuring either as a workaround will not make the connection valid.

Anthropic’s documented network destinations include:

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  • api.anthropic.com
  • statsig.anthropic.com
  • sentry.io

Ask the network administrator to verify that these destinations are allowed for the current installation and that TLS inspection, authentication, or DNS filtering is not interrupting the session. Allowlist details can change, so confirm them against the current documentation rather than copying an old firewall rule. Retest with verbose output after each network change.

A symptom-driven recovery sequence

Use this order when you are unsure which branch applies:

  1. Identify the product: Claude.ai or Claude Code.
  2. Record the symptom: missing, greyed out, upload failure, not selected, direct invocation failure, or broad runtime/network failure.
  3. Check access: in Claude.ai, confirm code execution and organization policy; in Claude Code, confirm the installation and scanned directory.
  4. Check the artifact: verify exact SKILL.md casing, a simple lowercase-hyphenated directory name, and valid YAML frontmatter.
  5. Check discovery: ask Claude Code to list skills or confirm that Claude.ai shows the enabled skill.
  6. Check matching: use a focused request that echoes the description and, where supported, try the direct slash command.
  7. Check the session: run claude doctor and repeat with --verbose if the environment still behaves unexpectedly.
  8. Check the network: only after local and account checks, investigate proxy variables, unsupported SOCKS or NO_PROXY settings, and firewall destinations.

After each fix, repeat the same minimal test. Changing the request, skill text, installation, and network simultaneously removes the evidence needed to identify the original cause.

Common mistakes that waste troubleshooting time

  • Editing instructions before checking access: no wording change can enable a skill disabled by code-execution or organization policy.
  • Changing capitalization casually: SKILL.md is case-sensitive; renaming it to a visually similar form can make a valid skill disappear.
  • Using a vague description: Claude may correctly decide that a general request does not match.
  • Assuming automatic matching is the only test: a direct slash command, when supported, isolates matching from availability.
  • Treating claude doctor as a skill validator: it diagnoses the broader installation, not every metadata or instruction error.
  • Applying old network instructions: proxy destinations and setup requirements are volatile; verify current documentation before changing a corporate firewall.
  • Installing with elevated npm permissions by default: sudo npm install -g can introduce permission and security problems.

What to collect before asking for support

A concise evidence bundle lets an administrator or support engineer reproduce the failure without exposing the entire project. Record:

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  • Whether the failure occurs in Claude.ai or Claude Code.
  • The exact symptom and the smallest request that reproduces it.
  • Whether code execution is enabled and whether an organization policy controls skills.
  • The skill directory name and confirmation that the file is exactly SKILL.md.
  • The frontmatter error, validator output, or other exact message, with secrets removed.
  • Whether the skill appears in the available-skills list and whether a direct slash command works.
  • The output of claude doctor and the relevant section of verbose output.
  • Whether the same test succeeds outside the corporate proxy or firewall.

Do not paste API keys, proxy credentials, private source files, or personal data into a support request. Redact those values while preserving the command, error wording, version, and sequence of steps.

Quick decision guide

If you observe Do this next
Claude.ai has no Skills section Verify code execution, then ask an owner whether organization policy or your role disables skills.
Claude.ai shows Skills but controls are greyed out Check code execution and creation permissions; an owner may need to enable the capability.
Claude.ai skill is enabled but ignored Confirm the toggle, sharpen the description, and submit an explicit matching request.
Claude Code cannot upload or load the skill Check the scanned directory, exact SKILL.md casing, lowercase-hyphenated name, and YAML frontmatter.
Skill is listed but automatic matching fails Rewrite the description around concrete tasks and triggers; test a direct slash command if available.
Direct invocation fails too Inspect permissions, packaging, validator output, installation, and session diagnostics.
Several sessions fail only on a company network Review supported HTTP/HTTPS proxy settings and current firewall destinations; SOCKS and NO_PROXY are unsupported.

The fastest reliable path is to prove each layer in order: access, file validity, discovery, matching, runtime, and network. Once a layer passes, leave it unchanged and investigate only the next failing layer.

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