Check the mailbox in Outlook on the web first; if messages received after October 2 appear there, the mailbox is working and the Outlook for Mac client needs to be reconnected or resynchronized.
1. Determine whether the issue is limited to the Mac
Open Outlook on the web in a browser and check whether current messages are present.
- Current mail appears online: Continue with the Mac steps below.
- Mail is also missing online: This is an account or mail-server issue rather than a Mac cache issue. Contact the email provider or, for a work or school account, the Microsoft 365 administrator.
Because the iPhone is receiving new mail, a Mac-side problem is more likely, but checking the web mailbox establishes where the authoritative mailbox currently stands.
2. Check Outlook’s connection on the Mac
In Legacy Outlook for Mac:
- Select Outlook on the menu bar.
- Ensure Work Offline is not selected.
- Select Tools > Accounts.
- Select the affected account in the left pane.
- For an Exchange account, look for an orange status indicator, which means Outlook is having trouble connecting to the server. ^1^
If the account requests credentials, enter the current password. For a non-Microsoft POP or IMAP account, obtain the correct incoming-server, SSL, port, username, and password settings from the email provider. ^2^
3. Refresh the affected folder’s cache
If this is an Exchange, Microsoft 365, or Outlook.com account, and the latest mail appears on the web:
- Back up any Outlook information that might exist only on the Mac.
- In Outlook’s navigation pane, right-click or Control-click the Inbox that stopped updating.
- Select Properties.
- Open the General tab.
- Select Empty Cache.
- Leave Outlook open and connected while it downloads the folder again.
Emptying the cache replaces that folder’s local contents with the latest server copy. It can delete information that has not synchronized to the server, so do not perform it until the web mailbox has been checked and any local-only data has been protected. ^1^
Send a new test message from another address. It should appear both on the web and in Outlook for Mac after synchronization finishes.
If Outlook displays a specific sync error
If Outlook says “We’re having trouble syncing the mailbox. Please remove and add your account again,” Microsoft has documented an intermittent Mac synchronization issue. Its current workaround is:
- Open Outlook on the web.
- Open People.
- Under the mailbox, select Favorites.
- Delete all favorite contacts.
- Restart Outlook for Mac and test synchronization. ^3^
Use this workaround only if that matching error appears. If the account still shows an orange connection indicator or cannot authenticate afterward, contact the email provider or Microsoft 365 administrator with the account type, Outlook version, and whether current mail is visible on the web.
References
- I'm not receiving email or other items in my Exchange account in Outlook for Mac | Microsoft Support
- I can't send or receive messages with Outlook for Mac | Microsoft Support
- Outlook for Mac and Outlook Mobile intermittently stop syncing | Microsoft Support