Hi Mr Brainfreeze,
For Classic Outlook on Windows, this behavior can sometimes occur when Outlook’s saved sign‑in token/credentials or the Outlook profile becomes stuck after an update, especially when both a work account and a personal Microsoft account are configured on the same PC.
In most cases, you don’t need to uninstall/reinstall Outlook (which can disconnect local PST archives and cause rule loss if they weren’t exported).
Please try these steps in order:
1) Make sure Outlook isn’t offline
- Outlook > Send/Receive tab > confirm Work Offline is off
- Click Send/Receive All Folders
Expected result: bottom‑right status shows Connected and mail starts updating.
2) Clear stuck Outlook sign‑in credentials
This usually fix many “Sign in” loops and “account already added” errors.
- Close Outlook completely
- Open Control Panel > Credential Manager
- Under Windows Credentials and Generic Credentials, remove entries clearly related to:
- Outlook / Office / MicrosoftOffice
- ADAL / MSAL
- Exchange
- The affected email address
- Restart the PC, then open Outlook and sign in again
3) Create a new Outlook profile
This does not delete your old profile. It remains available as a fallback.
- Close Outlook
- Control Panel > Mail > Show Profiles > Add
- Set the new profile as default
- Add the personal account first, then the work account
If you have local data:
- Reattach PSTs: Outlook > File > Account Settings > Data Files > Add
- Export/import rules to avoid loss: Home > Rules > Manage Rules & Alerts > Options > Export / Import
About turning updates off
You can disable Office updates via File > Account > Update Options > Disable Updates, but this isn’t recommended long‑term since updates include security fixes.
If it still won’t sync, please reply with:
- What the Outlook status bar says (Connected / Working Offline / Disconnected)
- Whether the personal mailbox updates at Outlook.com in a browser
- The exact wording of the “account already added” message (in quotes)
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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