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Interesting to see Google have introduced an “Undo Send” feature in Gmail.
Personally I think this is a great feature – and in fact I have a similar setup in Outlook/Exchange 2007 via an Outlook rule.
This means that all emails sit in my Outbox for 1 minute before sending, so I can prevent those “uh-oh!” moments. I also have the option of over-riding the rule by categorising the email as “Send Immediately” (I then have another rule which clears categories on outgoing emails so others aren’t annoyed by my systems).