This behavior may occur if the following conditions are true: Outlook is running in Cached Exchange Mode. * Kindly Mark and Vote this reply if it helps please, as it will be beneficial to more Community members reading here. When you enable the Do not deliver before option to defer the delivery of a Microsoft Office Outlook e-mail message, the message may not be delivered at the scheduled time. Marvin - * Beware of scammers posting fake support numbers here. For your reference, see the instruction below. Turn off Cached Exchange Mode to make sure your account is in online mode. ![]() To avoid this situation, you can keep Outlook running and make sure Outlook syncs with the server at the scheduled delivery time. Select New Email to start composing your new email message and then click the Options tab on the ribbon and then Delay Delivery. In this scenario, if your close Outlook, the email cannot be sent. In this offline folder file, rather than email server side. And the delayed delivery email will be stored If your Office 365 account has been enabled Cached Exchange Mode, your mailbox data will be copied from the server to your local disk a local offline folder file. ![]()
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