How to Request a Delivery Receipt in Outlook
When sending email, you might want to know that your message has been delivered (delivery receipt) and you might want to know whether the message was opened (read receipt). You can request one or both types of receipts easily in Outlook 2013.
NOTE: The recipient generally has the option of declining the sending of receipts, preventing you from receiving either type of receipt even though you request them. Additionally, not all e-mail programs support the sending of delivery and read receipts.
We will show you how to request delivery and read receipts for all emails you send and for a single message.
To choose to request delivery and/or read receipts for all emails you send out, click the File tab.
At the left side of the Account Information screen, click Options in the list of menu items.
On the Outlook Options dialog box, click Mail in the list of menu options on the left.
Scroll down to the Tracking section on the right side of the dialog box. Select the Delivery receipt and/or Read receipt check boxes to request receipts for all emails you send out. Select any other Tracking options you want and click OK to accept your changes.
If you only want to request a delivery receipt and/or read receipt for the current email message, click the Options tab while the message is open.
In the Tracking section of the Options tab, select either the Request a Delivery Receipt check box or the Request a Read Receipt check box or both.
Note that even though you receive a read receipt, that is not a guarantee that the recipient read and understood the email.
Credit: How to Request a Delivery/Read Receipt in Outlook