Fix Apple Mail Messages Disappearing When Sent to Office 365
Question details
Users experience emails sent from the Apple Mail app to Microsoft 365 recipients failing to arrive and vanishing from both Sent and Drafts folders.
- Product
- Microsoft 365 / Apple Mail
- Device & OS
- not provided
- Scenario
- Sending emails from Apple's native Mail app to Microsoft 365 recipients.
- Observed behavior
- Messages appear to be sent but do not reach the recipient's server and disappear completely without being saved in the Sent or Drafts folders.
Ensure you have a stable internet connection and verify the recipient's email address. If you are an IT administrator, ensure you have access to the Exchange Admin Center before proceeding.
Run a Message Trace in Exchange Admin Center
Use the Microsoft 365 admin center to determine if the message ever reached the recipient's server.
This method requires administrator privileges. It allows you to track the exact mail flow and pinpoint whether the email was dropped by the server, rejected, or delivered successfully.
Log in to the Microsoft 365 admin center with administrator credentials and navigate to the Exchange admin center.
In the left-hand menu, go to Mail flow, then select Message trace.
Click on 'Start a trace'. Enter the sender's email address or the recipient's address in the respective fields.
Set the appropriate time range for when the email was sent, and click search to view the detailed routing results.
Test Sending via the Outlook Mobile App
Isolate the issue by checking if the problem is specific to Apple's native Mail app.
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- 1. Visit the WPS Website: Go to the official WPS Office website on your computer or mobile device.
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Frequently Asked Questions
Why do emails disappear from Apple Mail without going to the Sent folder?
This usually happens due to synchronization issues between the native Apple Mail app and the Exchange server. If the server drops the connection before the sync completes, the email may fail to send and fail to save locally.
Can standard users run a message trace in Microsoft 365?
No, running a message trace requires administrator privileges. You must contact your Microsoft 365 IT administrator to perform this action in the Exchange Admin Center.
How can I fix Apple Mail not syncing with my Office 365 account?
Try removing the email account from your Apple device settings and re-adding it using the 'Microsoft Exchange' option. Alternatively, use the official Outlook mobile app for a more reliable connection.
