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Delay Or Schedule Sending Email Messages. For your first question delayed delivery options are client side in cached mode and server side in online mode. If you are using Online Mode then you dont need to leave Outlook running.
On the Options tab in the More Options group click the Delay Delivery button. In the Properties dialog box do one of the following. So when using Cached Exchange Mode Outlook must be connected and open at the assigned delivery time for the delayed delivery message to be sent.
Under Delivery options select the Do not deliver before check box and then click the delivery date and time you want.
Delay the delivery of all messages. Log in to Gmail and click on Compose. If you are using Online Mode then you dont need to leave Outlook running. Learn how to do this in a few easy steps.