Hi @Wonderwhy
Does this issue occur on internal users or external recipients or both? Is there any difference if the user send the same email from OWA rather than Outlook?
Do all the emails sent from that user have this delayed issue?
I would suggest you check the message header for this delayed email, copy the message header of the email into the following link, and check where the delay happened:
https://mha.azurewebsites.net/
Here is an article about this: https://practical365.com/how-to-read-email-message-headers/
Please Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.
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