Claude Cowork With Multiple Accounts (2026)
Claude Cowork will work through a long task, including against Gmail, Google Calendar, Drive, and Microsoft 365. Each of those connectors is still one login.
Anthropic’s Google Workspace connector can access Gmail, Calendar, and Drive “for the Google account you’ve connected.” Switching the Google account changes which account Claude can reach. It does not add a second one. The Microsoft 365 connector is the same shape on the other side: one tenant, the one you authenticated.
Neither Claude nor Gemini lets one connector carry two accounts at once. Each authorizes a single Google account per connection, and the documented way to reach the other one is to disconnect and sign in again. A question that spans both inboxes cannot be answered in a single conversation. Carly answers it, because it holds all of them.
If the task is “check work and personal mail, then book around both calendars,” native Cowork cannot do that in one run. This page covers what each connector actually does, where the send path is Microsoft-only, and the setup that holds both accounts behind one Cowork connector.
What Cowork can see natively
| Your setup | What Cowork sees natively |
|---|---|
| Personal Gmail + work Google Workspace | One of the two Google accounts |
| Work Microsoft 365 + personal Gmail | One Microsoft tenant and one Google account — that pair works |
| Two Microsoft 365 tenants | The tenant you authenticated |
| Several calendars under one Google login | Yes, including shared calendars you can already open |
| Scheduled Cowork task | The same connectors, with write limits noted below |
The mixed pair — work Microsoft 365 and personal Gmail — is the one native connectors cover, because they are different products. Two Gmails, or work Google plus personal Google, fail.
What each native connector can do
Gmail. Search and read. Create drafts. Manage labels. Claude sends from Gmail with your approval. Google’s OAuth screen mentions send permission; Anthropic is explicit that send is not enabled.
Google Calendar. View events, including shared calendars on that account. Create, update, and delete events. Find mutual availability. Respond to invitations. Recurring meetings. A second Google login is still out of scope.
Google Drive. Search, read, upload, create folders, save Claude-generated files if code execution is on. Images inside Docs are not read.
Microsoft 365. The write tools that arrived in July 2026 can send mail, manage calendar events, and create or update files in OneDrive and SharePoint. They are off by default. They reject attachments. They need a live conversation: a scheduled Cowork run can read, but it will not send while you are away. See Claude Cowork limitations.
Claude can write into Microsoft 365 now, and an administrator decides whether you get to. Organizations that connected before the write tools shipped find them blocked until someone flips them on, anything with an attachment is rejected at the door, and each user has a cap on writes and sends. Carly handles the attachments, across all of the accounts you connect.
On Team and Enterprise, an Owner has to enable these connectors at the organization level before anyone can authenticate.
Carly is how you add a second account
Carly is the connector that holds more than one Gmail or more than one Outlook inside a single Cowork task. Each account is connected in Carly, not in Claude. On Team and Enterprise, an Owner may need to enable the Carly connector for the organization first; members then connect it themselves.
The setup
- Sign in at carlyassistant.com.
- Open carlyassistant.com/integrations.
- Find Gmail or Outlook, click Connect, and approve access.
- Click Connect again for the next account, choosing Use another account if Google or Microsoft preselects the first login, and keep going for as many as you want.
- Repeat for Calendar on each account that has one.
Carly connects to thousands of apps, so while you are on that page you can add your CRM, files, and anything else you want reachable in the same Cowork task.
Then add Carly to Claude:
- Click Get the Carly connector, then Connect, and sign in with your Carly account.
- In the Cowork task, open + → Connectors and enable Carly.
On Team and Enterprise, the Owner may need to enable the Carly connector for the organization first.
Ask across all of them
Draft a reply to the newest invoice thread. Do not send it yet.
Check all my email for invoices from the last 30 days.
Check all my calendars for conflicts Wednesday 9:00 to 12:00 Eastern, then book the review.
Native connectors versus Carly in Cowork
| Need | Native Google / Microsoft connectors | Carly |
|---|---|---|
| Search one connected account | Yes | Yes |
| Two Gmails or two Outlooks in one task | No | Yes |
| Work Google + personal Google | No | Yes |
| Work Microsoft 365 + personal Gmail | Yes, different connectors | Yes |
| Send from Gmail | Yes, once you approve each message | Yes, with the connected account’s permissions |
| Send from Microsoft 365 | Yes, no attachments, live conversation | Yes |
| Shared calendars under the connected Google login | Yes | Yes |
| Recurring multi-account workflows | No | Yes |
Carly offers free Zapier-style workflows; AI agents start at $35/month.
Quick fixes
| Problem | Fix |
|---|---|
| Second Gmail replaced the first | Keep both in Carly. Leave the native Google connector on one account or turn it off for the task. |
| Carly is installed but missing in Cowork | Open + → Connectors and enable it for the task |
| Team plan cannot add the Carly connector | Ask the Claude Owner to enable the Carly connector |
| Workspace blocks Google OAuth | Ask the Google admin to trust the app |
Frequently asked questions
Can Claude Cowork connect two Gmail accounts?
Not natively. The Google connector is one account. Carly is the straightforward way to make several Gmail accounts available in one Cowork task. Step-by-step: multiple Gmail accounts in Claude Cowork.
Can Cowork use work Microsoft 365 and personal Gmail together?
Yes. Those are different connectors. Two Gmails, or work Google plus personal Google, still need Carly.
Can Claude send email from my personal Gmail?
The native Gmail connector sends once you approve each message, but only while you are in the conversation. Carly sends from the connected Gmail without you having to be there. Native send exists on Microsoft 365, without attachments, in a live conversation.
Will a company Claude Team workspace see my personal inbox?
If you enable a connector that can reach the personal account inside that workspace, yes — the chat can retrieve it. Keep the personal account on a personal Claude login, or on Carly accessed from a personal login. Do not paste personal mail into a company workspace to work around the connector.
Related: What is Claude Cowork · Claude Cowork limitations · Claude + Gmail · Multiple Gmail accounts in Claude Cowork · Multiple Outlook accounts in Claude Cowork · Gmail and Outlook together in Cowork · Can Claude connect to multiple Gmail accounts? · Can Claude Cowork connect to multiple Gmail accounts?
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