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Course Resources

Frameworks, troubleshooting, and reference guides

What's in here?

Everything you need in one place: troubleshooting guides for common issues, security checklists, and external links to tools and documentation.

  • Troubleshooting by system
  • Security and data safety
  • External tool links
  • Setup and configuration

Troubleshooting

Cowork

Cowork will not start

Cause: Subscription expired or Claude Desktop outdated

Fix: Verify Claude Pro or Max subscription. Update Claude Desktop. Restart.

VPN conflict

Cause: Corporate VPN interfering

Fix: Disconnect VPN before using Cowork, or use a dedicated network.

Task stuck or slow

Cause: Large file or complex task

Fix: Tasks can take 5-15 minutes. If frozen 15+ minutes, restart.

Poor output quality

Cause: Vague prompt, missing context

Fix: Use CTOC framework. Add CLAUDE.md. Provide examples. Iterate.

Context lost

Cause: Context window exhaustion

Fix: Break into smaller tasks. Repeat constraints. Restart after 1+ hour.

File access denied

Cause: Missing permissions

Fix: Check folder permissions in settings. Move files to workspace folder.

MCP Connectors

Connector not connecting

Cause: Auth expired or misconfigured

Fix: Re-authenticate via Okta SSO. Check MCP config. Restart Claude Desktop.

No results from Jira/Confluence

Cause: Wrong project key or permissions

Fix: Verify project key. Check Atlassian account access. Simplify query.

Glean returns nothing

Cause: Query too specific or index delay

Fix: Broaden search terms. New content may take 24 hours to index.

Write operations failing

Cause: Missing write permissions

Fix: Verify edit/create permissions. Contact admin if needed.

Scheduled Tasks

Task did not run

Cause: Device asleep or app closed

Fix: Keep device awake and Claude Desktop open during scheduled time.

Wrong output

Cause: Input data changed

Fix: Check input file validity. Refine prompt. Run manually first.

Wrong frequency

Cause: Schedule misconfigured

Fix: Review schedule settings. Test with on-demand runs first.

Skills

Skill not loading

Cause: File missing or corrupted

Fix: Re-install: bunx skillsadd <name>. Check .claude/skills/ directory.

Wrong output from skill

Cause: Skill instructions mismatch

Fix: Review skill file. Modify constraints for your data format.

Unknown skill error

Cause: Misspelled or not installed

Fix: Check exact name. Run /help. Re-install.

Chrome Automation

Chrome automation not working

Cause: Chrome not open or extension missing

Fix: Open Chrome. Install Cowork extension. Grant permissions.

Elements not found

Cause: Dynamic content or page change

Fix: Wait for full load. Re-snapshot with agent-browser snapshot -i.

Auth popup blocking

Cause: SSO or 2FA interruption

Fix: Complete auth manually first. Then resume automation.

Security & Data Safety

Ask Yourself These Questions (In Order)

1
Does the task involve sensitive data?
YES: Stop. Do it manually or use an approved secure tool.
NO: Continue.
2
Can you anonymize or redact the sensitive parts?
YES: Remove names, IDs, and emails first. Then continue.
NO: Stop. Data is inherently sensitive.
3
Are files from trusted sources?
YES: Continue.
NO: Verify authenticity first.
4
Will Cowork modify files or systems?
YES: Set up human review gates. Never auto-send.
NO: Continue. Read-only is safest.
5
Does it need internet access?
YES: Only grant access to trusted domains.
NO: Safest option.

Pre-Execution Security Checklist

  • No passwords, API keys, or SSNs in workspace files
  • Cowork only has access to your workspace folder
  • Plugins set to Ask mode
  • Reviewed Cowork's execution plan before approving
  • Regulatory claims will be verified independently
  • Financial or compliance outputs will be manually checked
  • Shared playbooks contain no secrets or credentials
  • Role-based access control is set for shared folders
  • Claude Desktop is updated to the latest version