7. Files, Connectors and Approvals (Safely Extending Cowork's Reach)

In Episode 7 of Beyond Prompting, we examine how to extend Claude Cowork's reach across local directories, cloud services, and desktop applications without sacrificing security. Author Sho Shimoda breaks down the essential controls and permissions that protect your host environment while allowing AI agents to run complex operational tasks. In this episode, we cover:

• • Scoping File Access: Why you should grant access to narrow project folders rather than your root home directory, and how local file access relies on an active desktop application acting as a local broker.
  • Connectors Call Outward: How enterprise cloud connectors issue requests from Anthropic's cloud servers directly to public SaaS APIs, and why internal services behind a corporate firewall require a local MCP server instead.
  • The Three Approval Modes: Navigating Manual (confirming every individual action), Automatic (pre-approving familiar action types), and Skip (zero-prompt execution for bounded tasks) as trust in a workflow develops.
  • Computer Use Security: Why driving your desktop screen and pointer operates directly on your live machine without a sandbox—and why it should be treated with the same caution as handing an unlocked laptop to a colleague.

(Note for listeners: This episode covers Chapter 7 of Sho Shimoda's book RUNNING CLAUDE: The Operator’s Guide to Chat, Cowork and Claude Code, available on Amazon as the successor book to Master Claude: Chat, Cowork and Code).