One of the most common questions about Cowork is: "Where does my data go?" Here is the straightforward answer:

Conversation history is stored locally. When you work with Cowork, your conversation history — everything you type, every file you share, every response Cowork generates — is stored on your local machine. It is not uploaded to a central server for storage. It is not available to Anthropic engineers. It is not indexed in a searchable database.

Conversations are not captured in audit logs. If your organization uses audit logging to track tool usage, be aware that Cowork conversations are not part of that audit trail. This has two implications: first, your conversations are private; second, if your compliance requirements mandate audit trails for all AI interactions, Cowork in its current form may not meet that requirement.

Cowork is not designed for regulated workloads. This is an important boundary. If your work involves data subject to specific regulatory requirements — HIPAA for healthcare data, SOC 2 for certain security standards, specific financial regulations — Cowork is not currently designed for those use cases. The safety and compliance infrastructure for regulated workloads requires a different level of data handling, audit controls, and certification that Cowork does not yet provide.

This does not mean Cowork is unsafe. It means Cowork is designed for general professional work, not for workloads where regulatory compliance requires specific data handling guarantees. Know where that line is for your work, and respect it.

Beyond data safety, here are the operational practices that experienced Cowork users follow:

Use dedicated folders. Create a specific folder for your Cowork projects and working files. This keeps Cowork's work organized and makes it easy to find, back up, and manage files. Do not let Cowork scatter files across your system — point it at a dedicated workspace.

Back up important work. Cowork operates on your local files. If you are working on something critical, make sure it is backed up — whether through git, cloud sync, or manual copies. Cowork is reliable, but your local machine is not invulnerable. Treat Cowork outputs the same way you treat any important work product.

Review plans before execution. When Cowork proposes a multi-step plan — especially one involving file modifications, external service calls, or batch operations — review the plan before approving it. Cowork will show you what it intends to do. Take the two seconds to read it. This is especially important for operations that are difficult to undo.

"Don't delete anything" as a default. Adopt the habit of telling Cowork not to delete files unless you explicitly confirm. It is safer to let unnecessary files accumulate in a dedicated folder than to accidentally lose something. You can always clean up later; you cannot always recover deleted work.

Start sessions with context. At the beginning of a Cowork session, provide context about what you are working on, what files are relevant, and what your goals are. Cowork does not carry context between sessions unless you have set up personal context files through the Productivity plugin. A 30-second orientation at the start of each session saves minutes of confusion later.

MCP (Model Context Protocol) connectors are the bridges between Cowork and your external tools — your CRM, your calendar, your project management platform, your analytics tools. They are powerful, but they deserve careful setup.

Principle of Least Privilege — When configuring MCP connectors, give Cowork only the permissions it needs. If a workflow only requires reading data from your CRM, do not grant write access. If a connector only needs access to one project, do not give it access to your entire workspace. Start restrictive and expand only as needed.

Review connector configurations. Before activating a connector, read its configuration file. Understand what service it connects to, what operations it can perform, and what authentication it uses. MCP connectors are defined in JSON files — they are readable and auditable.

Test with non-critical data first. When setting up a new connector, test it with non-critical data before pointing it at production systems. Make sure it behaves as expected, respects the permissions you set, and handles edge cases gracefully.

Monitor connector activity. When Cowork uses a connector to interact with an external service, it tells you what it is doing. Pay attention to these notifications, especially in the early days of using a new connector. Once you are confident in the behavior, you can relax your monitoring.

As you install multiple plugins and start combining them — Sales plus Research, Finance plus Legal, Productivity plus everything — the workflows become more powerful but also more complex. Here is how to manage that complexity:

Understand what each plugin can access. Each plugin has its own skills, connectors, and capabilities. Know what data each plugin can reach and what actions each plugin can take. This is especially important when plugins share connectors to the same external services.

Build combined workflows incrementally. Do not try to create a five-plugin workflow on your first attempt. Start with two plugins working together. Get that right. Add a third. Building incrementally lets you identify issues early and understand how the pieces interact.

Document your workflows. When you create a multi-plugin workflow that works well, document it. Write down the steps, the plugins involved, the slash commands used, and any specific prompts that produce good results. Future you — and your teammates — will thank you.

Share what works. If you build a workflow that saves you significant time, share it with your team. The combination of custom plugins and documented workflows creates a form of team-specific tooling that improves over time as more people contribute.