Forum Discussion
OneDrive won't sign in until I log into an external account in Teams
OneDrive gets stuck on "Signing in" after every restart – Sign-in only works when I log into a second organization in Teams
I've noticed that OneDrive consistently gets stuck at the "Signing in" stage every time I restart my Mac.
I have tried several troubleshooting steps to resolve this issue, including:
- Quitting OneDrive completely and restarting the Mac.
- Running the ResetOneDriveApp.command reset procedure.
- Running the standalone version of the OneDrive reset procedure (ResetOneDriveAppStandalone.command).
- Removing the "OneDrive Cached Credential" entry from macOS Keychain Access.
- Testing the sign-in process through a web browser.
- Testing the connection using a mobile hotspot to rule out potential network-related issues.
- Updating the standalone OneDrive application to the latest available version.
Unfortunately, none of these steps has permanently resolved the issue. Even when OneDrive starts working again, it gets stuck at the sign-in stage after a subsequent restart.
However, I have discovered something quite interesting.
Recently, while preparing for a Teams meeting, I signed in to one of my two accounts in Microsoft Teams. At that exact moment, I noticed that OneDrive suddenly completed its sign-in process and started working normally, even though it had previously been stuck at the "Signing in" screen.
Here is how my account setup is configured:
- OneDrive is currently syncing folders belonging to my primary organization, as well as one shared folder from an external organization.
- I have two accounts configured in Microsoft Teams, representing my primary organization and the external organization.
- Both accounts are essentially associated with the same email address and my primary organization's Exchange account.
- The external organization's shared access also uses the same email address, but with some additional characters appended to the email address.
The interesting part is that OneDrive only manages to complete its sign-in process when I sign in to the external organization's account in Teams. Otherwise, it remains stuck in an endless sign-in loop.
This makes me wonder whether there is some kind of authentication dependency or token-sharing mechanism between Teams and OneDrive that is causing this behaviour.
What I would like to understand is:
- Is it possible to make OneDrive authenticate independently, without relying on signing in to the external organization's account in Teams?
- Is this expected behaviour when using multiple organizational accounts and shared folders across different Microsoft 365 tenants?
- Could a recent update to OneDrive, Teams, or macOS have introduced a change in how authentication tokens are handled?
What's particularly confusing is that I have been using exactly the same account configuration and setup for quite some time without any issues. This behaviour only started appearing after recent updates.
I'd really appreciate any insights or suggestions on how to resolve this permanently, rather than having to sign in to the external organization's Teams account every time I restart my Mac just to get OneDrive working.
Thank you in advance!
2 Replies
Your restart loop is tied to accessing external-tenant content, and Teams sign-in appears to unblock it. That does not prove both apps use an identical token or that Teams is a required OneDrive dependency.
Microsoft documents a B2B Sync limitation: the sync client cannot present interactive authentication for external guest content. Guest MFA or Terms of Use prompts can therefore interrupt synchronization. Mac also has a limitation when the invited address format differs from the address used by the sync app.
Ask both organizations’ administrators to compare Entra sign-in logs before and after the Teams login, checking the target tenant, resource, failure reason and Conditional Access result. Verify the invitation uses your intended organizational identity; don’t manually substitute the guest account’s modified username.
Avoid wiping every Microsoft Keychain entry. Your reset tests are sufficient; escalate with timestamps and app/macOS versions. I cannot confirm a specific update regression or permanent fix.
- oliverwilliamsCopper Contributor
That Teams link is a huge clue. Mac shares the exact same sign-in token between Teams and OneDrive. If Teams logs in second, it can mess with that token. Try a clean reset: 1. Sign out of both accounts in Teams. 2. Force quit OneDrive and Teams. 3. Open Mac Keychain Access and wipe every entry for Microsoft and OneDrive. You will have to re-enter passwords, but it is worth it. 4. Log into OneDrive first, before touching Teams. 5. Reboot your Mac to see if it actually holds. If it still begs for Teams, ping your IT admin. In my experience, external orgs often block OneDrive access until the main Teams account signs in.