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https://answers.microsoft.com/en-us/msoffice/forum/msoffice_outlook-mso_win10-mso_2016/why-doesnt-outlook-email-delay-delivery-happen/6ac0d3ba-28b8-4cbc-bffd-567d1c83fc50
Mar 16, 2017 · Based on this information you provided, delay delivery option will work as long as the computer has not been turned off since normally, sending email needs to be connected to the Internet. This means, if your computer is turned off, the delay delivery option will interrupt and will send the emails once you turned on your computer and got connected to internet.
https://docs.microsoft.com/en-us/exchange/troubleshoot/mail-delivery/email-delivery-issues
Mar 26, 2020 · Fortunately, Support and Recovery Assistant finds and helps you fix most issues with Outlook or Office 365. As a first step in troubleshooting email delivery problems for Office 365 for business, we recommend that you download and run Microsoft Support and Recovery Assistant on the affected machine.
http://helpdesk.cwsl.edu/components/default.asp?nav=faq.asp&body=faqs/email_faq9.asp
It is a problem with a remote email system that we have no control over. Our email gateway is able to connect to the remote email server, but that system is not accepting delivery of the message. Our system will attempt delivery 4 more times over the next 16 hours.
https://support.microsoft.com/en-us/help/2695805/how-to-troubleshoot-performance-issues-in-outlook
Nov 14, 2019 · Important This article contains a section that shows how to help lower security settings or how to turn off security features on a computer. You can make these changes to work around a specific problem. However, before you make these changes, we recommend that you evaluate the risks that are associated with implementing this workaround in your particular environment.
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