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I trialed an Outlook add-in that had a number of different functions, one of which allowed you to send the same email to multiple recipients at the same time, without doing it as a bcc. For example, if I wanted to send the same email to Tom, Dick and Harry without having to write 3 emails, the add-in let me specify the names and the email would go to the 3 of them. In my Sent Items folder would be 3 emails each addressed to the respective person.

The add-in might have started with an S, or an R, but I don't remember.

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up vote 1 down vote accepted

There is a free Send Messages Personally add-in from Outlook Freeware (starting with 'S') and a commercial product, ReliefJet Essentials for Outlook, (I'm one of its developers and its name starts with 'R').

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ReliefJet is the one! But I like your first suggestion even better since it's free, so +1 for that. – Matt Aug 19 '11 at 23:38

I think you are looking for the add-in called Send Personally:

Send Personally is the add-in for Microsoft® Outlook® designed to send individual emails to a great number of recipients via Microsoft Outlook 2010 / 2007 / 2003 / XP / 2000. This add-in for Outlook offers you an alternative method of sending personalized emails from Outlook: separate messages are being created for each recipient. The final recipient will receive no information about any of the other recipients. Moreover, he/she will see only his/her name and address in the "To" field, as if the message is sent to him/her only.

Note: You can also achieve the same result by using the Mail Merge feature in Outlook. This method does exactly what the Outlook add-in does and its FREE.

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Thanks for the Send Personally tip. – Matt Aug 19 '11 at 23:40

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