Is there a way of sending an email from Outlook with some sort of flag that tells Exchange to hold on to the message for 5 minutes before it is actually sent out on the internet?
I know about setting the "Do not deliver before" date in Outlook but that simply keeps the message in the Outlook outbox as far as I can see.
I'm happy to use redemption if it is able to help.
Try to set the MailItem.DeferredDeliveryTime
property (which sets the PR_DEFERRED_DELIVERY_TIME
property) - refer to this blog.