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https://support.office.com/en-us/article/Delay-or-schedule-sending-email-messages-026af69f-c287-490a-a72f-6c65793744ba
Delay the delivery of all messages. You can delay the delivery of all messages by up to two hours by creating a rule. Click File. Click Manage Rules & Alerts. Click New Rule. In the Step 1: Select a template box, under Start from a Blank Rule, click Apply rule on messages I send, and then click Next.
https://support.office.com/en-us/article/Sent-email-in-Outlook-com-comes-back-delivery-failed-45e048ac-f7b1-4c0f-b525-081cb34f1062
Most email service providers impose a limit on the size of messages their users can send or receive. Your message is too large for the recipient's email server. Try this fix: Instead of sending large attachments via email, upload them to OneDrive and send the recipient a link.
https://www.lifewire.com/schedule-emails-in-outlook-1173683
Jan 21, 2020 · If Outlook is not open and running at the time a message reaches its scheduled delivery time, the message is not delivered. The next time you launch Outlook, the message is sent immediately. If you use a cloud-based version of Outlook, such as Outlook.com, scheduled emails are sent at the correct time whether you have the website open or not.Author: Heinz Tschabitscher
https://www.howtogeek.com/254282/how-to-schedule-or-delay-sending-email-messages-in-outlook/
In the Delivery options section on the Properties dialog box, click the “Do not deliver before” check box so there is a check mark in the box. Then, click the down arrow on the date box and select a date from the popup calendar. Click the down arrow on the time box and select a time from the drop-down list.Author: Lori Kaufman
https://support.office.com/en-us/article/Add-delivery-receipt-to-track-an-e-mail-message-69cd1b39-2300-482d-96c6-22e2f4a96848
Get a delivery or read receipt In the open message, click Options. In the Tracking group, select the Request a Delivery Receipt or the Request a Read Receipt check box.
https://answers.microsoft.com/en-us/outlook_com/forum/all/why-am-i-receiving-mail-delivery-subsystem-errors/d6ca2cec-e591-4f74-9f74-877bd88fa1d1
Sep 07, 2015 · I believe that there is something going on wtih Microsoft and Hotmail (Outlook) which is allowing people to see your profile and then they send these bogus Mail Delivery Failure messages to bog down your IN BOX and SPAM folders.
https://support.office.com/en-us/article/Add-and-request-read-receipts-and-delivery-notifications-a34bf70a-4c2c-4461-b2a1-12e4a7a92141
A delivery receipt confirms delivery of your email message to the recipient's mailbox, but not that the recipient has seen it or read it. A read receipt confirms that your message was opened. In Outlook, the message recipient can decline to send read receipts.
https://outlook.live.com/owa/?path=/mail/inbox
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https://www.lifewire.com/request-delivery-receipt-outlook-1173704
Mar 19, 2020 · If you use Outlook in a workgroup environment and use Microsoft Exchange Server as your mail service, you can request delivery receipts for messages you send. A delivery receipt means that your message has been delivered, but it doesn't mean the recipient has seen the message or opened it.
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