Outlook email address visualizer plugin

This project has come about because of multiple times emails have been sent to incorrect contacts with sensitive content. For this reason I wish to create a plugin that does the following process: Upon hitting send the email is scanned- if it has any attachments OR contains key words from a key word list (that is customizable) a window comes up saying "this email is being sent to the following: <large bold font list of people in the "TO" and "CC" field>. Also, I would like to have a visual image of each person who is being sent the email's company logo. I dont know what would be the best way of doing this. If it would be referencing the image associated with the contact, or if you could google image search the domain name and auto insert the 1st/2nd/3rd image. The later would be preferable. From this window you can "CONFIRM" and then the email will be sent, or can "INTERRUPT" and the email will be pushed back to drafts folder. If the email does not contain an attachment or any words from the key word list then it is send without any window popping up. Please reply by outlining how you would intend to create this solution. I do not wish to pay for development if you do not have a fairly clear idea of how it can be done.