Hi Matt Ruddock,
This is looking like a pattern that typically occurs when desktop Outlook is added using a different identity or mailbox type than the one that supports the full Outlook.com (Exchange) experience.
In many cases, re‑adding the account using the exact @outlook.com alias (the same one that works on Outlook on the web) helps ensure Outlook provisions the mailbox as Outlook.com/Exchange. This is also the connection type required for newer integrations like Copilot and Microsoft To Do.
New Outlook for Windows
- Settings (gear) > Accounts
- Remove the account that’s missing Copilot
- Add the account again, signing in with your exact @outlook.com alias
The account is provisioned as Outlook.com/Exchange and feature availability aligns with Outlook on the web.
Classic Outlook (Legacy)
- Close Outlook
- Control Panel > Mail > Show Profiles > Add… (create a new profile)
- Add the account using the @outlook.com alias (not the older sign‑in address)
- Open Outlook using the new profile
In File > Account Settings, the account Type should show Exchange / Outlook.com (wording may vary). If it still shows IMAP or POP, remove and re‑add the account using the alias so it connects as Exchange.
Note: Creating a new profile or removing/re‑adding an account may temporarily remove locally cached mail until it fully re‑syncs from the server.
For reference:
- How to find and enable missing Copilot button in Microsoft 365 apps
- Copilot is missing, disabled, or doesn't work correctly
- Add or remove an email alias in Outlook.com
Next step (to confirm)
- In Classic Outlook > File > Account Settings, what is the account Type (Exchange vs IMAP/POP)?
- In Word > File > Account, which signed‑in address is shown (alias vs original sign‑in)?
Please let me know if this proves useful to you, or if you would like further assistance.
I'm looking forward to your reply.
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