Setting up Microsoft 365 apps on macbook running Sonoma

Question

I have spent the past 3 hours attempting to get the Microsoft 365 apps set up and logged in. I'm trying to set up my old 2018 macbook air for my partner to use as their work computer. I have updated the computer to be running macOS Sonoma 14.8.4, and downloaded + installed the current versions of Microsoft 365 apps (16.106) through his work account. There are no problems logging into his account on the web versions of the apps, but none of the desktop apps will log in - I've also tested with my work microsoft account and get the same error messages. I've been using copilot to troubleshoot and have tried (multiple times) clearing caches, deleting files from keychain, uninstalling and re-installing the apps, with/without a VPN, on home wifi and mobile hotspot, and absolutely nothing is working.

The error messages include:

• Outlook - "Sorry! We couldn't find a match. Please choose the provider", then try selecting Microsoft 365, then get "Authentication couldn't be completed".
• Teams - "No network connection. Please check your network settings and try again. [2604]"
• OneDrive - "There was a problem connecting to onedrive" then the same message about network connection.
• Word - just a blank window and no log in option
• Microsoft AutoUpdate - "AutoUpdate cannot connect to the update server"

Please help!!

Answer 1

Hi @Sarah Mc

Thank you for reaching out to Microsoft Q&A forum.

Based on the information you shared, I understand that you are trying to set up Microsoft 365 desktop apps on a 2018 MacBook Air (macOS Sonoma 14.8.4) for your partner. While you can successfully sign in to the web versions, none of the desktop apps (Outlook, Teams, OneDrive, Word) allow sign-in and show various authentication or network-related errors, even after trying multiple troubleshooting steps such as clearing caches, reinstalling apps, removing Keychain items, and testing different networks.

To help narrow this down, could you first confirm where you downloaded the Office apps from? For example:

• Directly from portal.office.com through the work account
• The Mac App Store
• Or from another download source

In the meantime, please try the following steps:

1. Remove existing Office license data

Use the Microsoft License Removal Tool for Mac to clear any corrupted or conflicting license information. After running the tool, restart the Mac.

2. Reinstall Office using the official installer

Go to the Update history for Office for Mac page and download the latest stable installer package from there. Install the apps again and then try signing in with the work account.

3. Test with a new macOS user profile

Sometimes the issue is related to a corrupted user profile. You can try:

• Creating a new macOS user account
• Signing into that new profile
• Installing Office again and testing sign-in there

If the issue still occurs after these steps, please let me know more details, I’ll try to help narrow down the root cause further.

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Answer 2

All Microsoft 365 desktop apps on macOS Sonoma showing “no network / can’t connect / can’t authenticate” while web apps work indicates a sign-in/activation and connectivity problem specific to the installed apps, not the accounts or the Mac’s general internet.

From the provided information, the following points apply:

1. Microsoft 365 desktop apps are full local apps and do not need to be online all the time to run, but they do require:
   • Internet connectivity for first-time install and initial activation.
   • Periodic connectivity (roughly every 30–39 days) so the subscription and license can be verified; otherwise the apps go into reduced functionality mode.
   This is described for both consumer and enterprise subscriptions:
   • “You’ll need internet access to do any of the following: first time install, initial activation of the Microsoft 365 desktop apps, install updates or reinstall the apps, manage your subscription, and access documents stored on OneDrive.”
   • “If you don’t connect to the internet at least every 39 days, your apps will go into reduced functionality mode… To reactivate the Microsoft 365 apps, simply reconnect to the internet and sign in to Microsoft 365.”
2. For Microsoft 365 Apps in an organization (work account):
   • The user must have a valid Microsoft 365 account with a license assigned.
   • If the license or account is missing or removed, the apps go into reduced functionality mode.
   • Users do not need to stay connected all the time, but must connect at least every 30 days to verify subscription status.
3. When activation or account verification fails, Microsoft 365 Apps can show errors like “We couldn’t verify the subscription” or “Unable to verify the account,” and most features are turned off. The official guidance for such account/subscription verification issues is:
   • Make sure the apps are fully updated (from any Office app: File > Account > Update Options > Update Now).
   • Reset the Microsoft 365 activation state.
   • Change the password and sign in again, ensuring the correct Work or School account is used.
4. For sign-in failures in desktop apps specifically, there is a known class of issues where authentication fails even though the network is fine. In those cases, the recommended steps include:
   • Rebooting the device.
   • Repairing the Windows Web Account Manager (WAM) plug-in on Windows. (This part is Windows-specific and does not apply to macOS, but it shows that sign-in failures can be caused by the client-side authentication component rather than the account or network.)

Based on the context, the concrete steps that are supported are:

1. Confirm licensing and account type
   • Verify that the work account being used on the Mac has an appropriate Microsoft 365 Apps license assigned. If the license is missing or expired, the desktop apps will not activate and will remain in reduced functionality mode.
   • If there is any doubt, an admin should check the user’s license in the Microsoft 365 admin center (per “Check which Microsoft 365 business product or license you have”).
2. Ensure the apps can reach Microsoft 365 services for activation
   • The apps must be able to reach Microsoft 365 activation and update endpoints. If there is any network-level filtering (corporate firewall, DNS filtering, security software, or VPN configuration), it can block:
     • Activation
     • Sign-in
     • Microsoft AutoUpdate
   • Since the same behavior occurs on home Wi‑Fi and hotspot, check whether any security software or content filter is installed on the Mac that might be blocking Microsoft 365 endpoints.
3. Update Microsoft 365 Apps fully
   • Open any Office app that will launch (for example, Word).
   • Go to File > Account.
   • Under Product Information, choose Update Options > Update Now.
   • Let the update complete, then restart the apps and try sign-in again.
4. Reset the activation state
   • Follow the documented procedure to “Reset activation state for Microsoft 365 Apps for enterprise,” then start an Office app and sign in again with the work account.
   • This clears cached activation data that may be corrupted and forces a fresh activation against the service.
5. Sign out and sign in again with the correct account
   • In an Office app (such as Word):
     1. Select the name/profile icon at the top.
     2. Sign out of all accounts.
     3. Close all Office apps.
     4. Reopen an Office app and sign in using the Work or School account (not a personal Microsoft account).
   • After signing in, check whether the apps now activate and whether Outlook/Teams/OneDrive can authenticate.

If, after confirming a valid license, updating the apps, resetting activation, and signing in with the correct work account, the desktop apps still cannot connect while web apps work, the next step is for the organization’s Microsoft 365 admin or support to review:

• Whether any conditional access, device compliance, or network access policies are blocking macOS desktop clients while allowing browser access.
• Whether there are any known issues with Microsoft 365 sign-in for macOS clients in that tenant.

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References:

• What's the difference between a paid Microsoft 365 subscription and the free web apps?
• About Microsoft 365 Apps in the enterprise
• Account or subscription verification errors activating Microsoft 365 Apps