Start here

Connect Microsoft 365

Connecting Microsoft 365 lets Winston work with Outlook mail, OneDrive, SharePoint, and Word, Excel and PowerPoint files. It takes one click in Winston and a Microsoft sign-in. This page shows each screen.

Before you start

You need to be an Owner or Admin in Winston.
Decide which Microsoft account Winston should use. Winston acts as that account: email is sent from it and files are saved to its OneDrive. A shared account such as winston@yourcompany.com often works best.
The account needs a mailbox (a Microsoft 365 license that includes Exchange Online) for Outlook, and OneDrive or SharePoint for files. It does not need a Microsoft admin role.
Allow your browser to open a popup from Winston. The Microsoft sign-in happens in it.

The connection belongs to the Winston workspace, not only to you. Anyone in the workspace who asks Winston can have it read that account's mail and files, and anything Winston sends goes out under that account's name. Choose the account with that in mind.

Microsoft 365 is a separate card from Microsoft Teams. Teams lets your team chat with Winston; Microsoft 365 lets Winston work with mail and files. For Teams, see Use Winston in Microsoft Teams.

1. Connect it in Winston

In Winston, open Settings → Connections, find the Microsoft 365 card (under Productivity, or type "Microsoft" into the search box) and choose Connect.

The Connections screen in Winston searched for Microsoft, with the Microsoft 365 card's Connect button outlined — Settings → Connections. Find Microsoft 365 and choose Connect.

The dialog is badged OAuth 2.0: Winston never sees the Microsoft password, only an authorization Microsoft can withdraw. It repeats which account Winston will act as and carries an approval link for your Microsoft 365 admin, which you only need if Microsoft asks for admin approval (see below). Choose Connect with Microsoft 365.

Winston's Microsoft 365 dialog, badged OAuth 2.0, explaining that Winston acts as the signed-in account, with an admin approval link and the Connect with Microsoft 365 button — Connect with Microsoft 365 opens a sign-in window.

While the sign-in windows are open, the dialog in Winston waits. If the window was blocked or you closed it early, choose Reopen Popup.

A small window opens, headed Link Microsoft 365 Account. Choose Connect. It opens Microsoft's sign-in in another window and shows Connecting… until you finish.

The link window headed Link Microsoft 365 Account, with a Connect button — The link window. Connect opens Microsoft's sign-in.

Sign in as the account Winston should use. Microsoft then asks for that account's password, passkey or other sign-in method, depending on how your organization set it up.

Microsoft's Sign in page with an Email or phone field, a Next button and Sign-in options — Microsoft's own sign-in. Enter the account Winston should act as.

Microsoft may ask Stay signed in?. Either answer works; it only affects your browser, not the connection.

Microsoft's Stay signed in? page for the account, with No and Yes buttons — Stay signed in? only affects this browser. Either answer is fine.

The first time an account connects, Microsoft may also show a Permissions requested page listing what Winston will be able to reach. Read it and choose Accept. Accounts that have approved Winston before skip this page.

3. Check it is connected

The link window reports Success and closes on its own.

The link window reporting Success: you've successfully set up your Microsoft (Tenant) integration — Microsoft accepted the sign-in. The window closes by itself a moment later.

Back in Winston the dialog changes to Microsoft 365 is connected. Choose Done. Nothing else needs to be set up.

Winston's dialog headed Microsoft 365 is connected, saying Winston can now use your Microsoft 365 account, with a Done button — Winston confirms the connection. Choose Done.

The Microsoft 365 card on the Connections screen with a green Connected badge, next to the Microsoft Teams card — The Microsoft 365 card after connecting. The plug icon in its corner disconnects it again.

Then ask Winston a small read-only question in Chat to confirm it reached the right account, for example "Which Microsoft account are you connected as, and what are the subjects of my three latest emails?" or "List the folders in my OneDrive." Winston names the account it is using. If it is the wrong one, disconnect and connect again signed in as the right account.

Asking for mail or files works like any other question in Chat, with the same rules about what needs reviewing before anything is sent or changed. See Asking Winston and Review and approve.

If Microsoft says "Need admin approval"

Some organizations only let an administrator approve new apps. In that case Microsoft shows Need admin approval instead of letting you continue. Close the window, and send your Microsoft 365 admin the approval link from Winston's Microsoft 365 dialog. They open it once and approve Winston for the organization. Then choose Connect with Microsoft 365 again and sign in as the account Winston should use.

Admins: don't choose "Sign in with an admin account" on the Need admin approval screen. That connects Winston to the admin's own mailbox rather than the account you meant. Use the approval link instead.

Disconnect

To stop Winston using the account, choose the plug icon on the Microsoft 365 card and confirm Disconnect. This applies to the whole workspace.

Disconnecting in Winston does not withdraw the approval on Microsoft's side. To do that as well, the account's owner removes Winston at myapps.microsoft.com, or an admin removes it in the Microsoft Entra admin center. To switch to a different account, disconnect first and run the steps above again with the other account.

If something does not work

What you see	What to do
"Could not open authorization popup"	Your browser blocked the popup. Allow popups for Winston, then choose Connect with Microsoft 365 again, or choose Reopen Popup.
"Need admin approval" at Microsoft	Your organization only lets admins approve new apps. Send your Microsoft 365 admin the approval link from the Winston dialog, then connect again.
Microsoft signs in straight away as the wrong account	Your browser is already signed in to Microsoft. Sign out of Microsoft in that browser (or use Sign-in options to pick another account), disconnect in Winston, and connect again.
Winston says the mailbox is not enabled, or mentions MailboxNotEnabledForRESTAPI	The account has no Exchange Online mailbox. Give it a license that includes Exchange Online, or connect an account that has a mailbox. Files in OneDrive and SharePoint can still work.
Winston can read files but not a particular SharePoint site	Winston sees what the connected account can see. Give that account access to the site in SharePoint.

For other connections, see Connect your tools. Anything else, see Troubleshooting or contact Support from the dashboard.