Onlooker

From Polychrome:

This new software launched as an add-in for Microsoft Outlook helps prevent users from the embarrassment of forgetting to include an attachment when they meant to do so. Be honest, at one time or another we've all sent an email promising an attached file with further information on a specific topic and forgotten to actually attach the file. If you are lucky you realize what you have done within a few minutes and can correct the situation with a quick follow up email, this time including the attachment. But sometimes you only realize what you have done when you receive a response asking where the attachment is. Hopefully when this happens the email is to friends or colleagues where the damage is limited to only minor embarrassment, but if the email is to the boss or even worse a customer or prospect, then you could be responsible for creating the impression that you don't pay enough attention to detail or that your organization is always in a rush and too busy to give customers the attention they deserve. Onlooker sits unobtrusively in your Microsoft Outlook email client and monitors your outgoing emails. Described as "a friend in your outbox" Onlooker has an intelligent and customizable email content recognition system that prevents you from forgetting to add attachments.

How does it work? When you send an email, Onlooker checks your message and looks for specific search terms in the text like "ATTACHED" and checks the number of attachments added to this email. There are a number of built in search terms for the most common phrases that people use when they mean to attach a file and users can even add their own search term if they find that they commonly use different phrases to indicate that a file should be attached. If Onlooker determines that you have forgotten to add your attachment it will prompt you with a message reminding you. Of course it is possible to quickly dismiss the message with a single click, or stop and add your attachment.

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