Break-Fix Troubleshooting

Purpose

Use this skill to turn a failing caddy-security deployment into either a concrete fix or a high-quality break-fix report. Treat the repository skills in .codex/skills as the primary task documentation; https://docs.authcrunch.com is legacy context, not the source of truth.

Workflow

1. Identify the intended auth flow, protected routes, observed symptom, expected behavior, and whether the failure happens during Caddyfile adaptation, provisioning, login, callback handling, authorization, upstream proxying, or token/session validation.
2. Gather evidence before diagnosing: full Caddyfile, relevant Caddy logs, browser or HTTP status details, caddy version, caddy list-modules --versions | grep -E "(auth|security)", operating environment, recently changed config, and last known working version when available.
3. Redact secrets while preserving directive names, route structure, identity provider names, policy names, cookie names, issuer URLs, redirect paths, roles, claim names, and module versions.
4. Load the relevant repository skills: configuration for Caddyfile analysis, then the specific domain skills for authentication portals, authorization policies, identity stores, OAuth providers, SSO/SAML, credentials, messaging, users, secrets, registrations, or runtime resolution. Use testing-and-ci when validation requires tests, fixtures, or CI reproduction.
5. Compare the configuration to the parser files and fixtures named by the loaded skills. Prefer the smallest valid corrected configuration over a broad rewrite.
6. Validate with the narrowest available command. Use Caddy adaptation or focused Go tests when local context supports it; otherwise describe the exact command the reporter should run.
7. Report the root cause, the minimal fix, validation performed, remaining uncertainty, and any repository-skill gap discovered during the work.
8. Write a GitHub-issue-ready Markdown report under tmp/breakfix/ unless the user explicitly asks not to create files.

Symptom Checks

• Adapt or provision errors: check directive placement, block nesting, argument counts, module availability, external plugin registration, and env or secret placeholder resolution.
• Login failures: check enabled identity stores/providers, portal path routing, credentials, user transforms, cookie settings, crypto keys, and clock skew.
• Portal API failures: check Accept: application/json or format=json, portal base path, latest sandbox_secret in challenge flows, token source headers/cookies, /beacon versus /whoami semantics, and whether admin endpoints have enable admin api plus an admin session.
• Sandbox or MFA lockouts: check checkpoint order, require mfa transforms, registered TOTP/U2F tokens, sandbox expiration, repeated password failures, MFA failure counters on the user record, and whether the user is being forced to register an MFA token during login.
• OAuth/OIDC callback failures: check redirect URI, issuer/discovery URL, client ID/secret, scopes, PKCE settings, state/cookie behavior, trusted redirects, reverse-proxy headers, and provider-specific constraints.
• SAML failures: check entity IDs, ACS URLs, certificates, signing keys, metadata, role attributes, and whether the issue is an identity-provider flow or an SSO app-provider flow.
• LDAP failures: check bind credentials, search base, filters, username and group attributes, realm, TLS settings, network reachability, exact one-user search results, role-producing group mappings, and the service-bind then user-rebind flow.
• Registration failures: check messaging provider delivery, confirmation link base URL, passcode expiry, domain/MX restrictions, dropbox path, admin email, target identity store, and whether manual approval or database transfer is still required.
• Authorization denials: check route order, authorize with <policy> wiring, token cookie/header availability, verify keys, ACL rules, roles, claim names, bypass rules, and injected identity headers.
• Basic/API-key auth failures: check X-Auth-Realm or configured realm header, API key header name, one with ... realm ... line per accepted realm, System API keys for remote portals, and whether the response is a 401 auth failure or a browser-style redirect due to missing credentials.
• Redirect loops or missing sessions: check cookie domain/path/security flags, auth URL, same-site behavior, source address validation, TLS termination, and whether authn and authz use matching crypto material.
• Runtime replacement or secrets issues: check unresolved {env.*} tokens, secret IDs, configured secrets manager modules, fallback behavior, and resolved fixture expectations.

Response Shape

When solving the issue directly, include:

• Root cause and confidence level.
• Minimal config change or explanation of the required deployment change.
• Evidence used, including relevant log lines or module versions.
• Validation commands run or recommended.
• Security notes about redacted or unsafe material.
• Remaining questions only when they block a reliable fix.

When helping a reporter file a break-fix issue, fill or request the fields from .github/ISSUE_TEMPLATE/break-fix.md: issue description, skill-guided troubleshooting prompt and findings, full redacted Caddyfile, logs/errors, version information, expected behavior, actual behavior, skill/documentation gap, and additional context.

Issue Report File

For break-fix issue preparation, create tmp/breakfix/ if it does not exist and write a Markdown file named with this pattern:

YYYYMMDD_HHMM_<short-issue-slug>.md

Use the local timestamp at report creation time. Keep the slug short, lowercase, and hyphen-separated, such as oauth-callback-loop or ldap-bind-failure.

The Markdown file must contain enough information to create a GitHub issue from .github/ISSUE_TEMPLATE/break-fix.md without reconstructing context from the chat. Include these sections:

• # breakfix: <concise title>
• ## Describe the issue
• ## Skill-guided troubleshooting
• ## Configuration
• ## Logs and errors
• ## Version information
• ## Expected behavior
• ## Actual behavior
• ## Skills or documentation gap
• ## Additional context

Preserve fenced code blocks for Caddyfiles, logs, commands, and version output. Redact secrets, tokens, cookies, passwords, and private keys, but keep names, routes, roles, claims, issuer URLs, redirect paths, and module versions needed for diagnosis. Use TODO only for fields the reporter still needs to provide.

Skill Gap Feedback

If repository skill guidance was missing, incorrect, ambiguous, or not specific enough for the issue, capture:

• The exact prompt or task that produced the weak guidance.
• The smallest redacted Caddyfile and log excerpt that demonstrates the gap.
• The correct behavior or configuration pattern, with parser or fixture references when possible.
• The skill file that should be updated, if identifiable.

Prefer turning repeated support issues into skill improvements so future agents can generate secure, production-ready guidance on the first attempt.