Outlook Delivery receipts are not supported in a Hotmail account
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If you request both a read receipt and a delivery receipt for messages that you send, and then send messages using your Hotmail account, you receive a read receipt, but you do not receive a delivery receipt.
This behavior occurs because Hotmail does not support delivery receipts.
To work around this behavior, select read receipts to confirm that the recipient has opened the message. To do this:
On the Tools menu, click Options.
Click E-mail Options.
Click Tracking Options.
Click to select the Request a read receipt for all messages I send check box, and then click OK.