Sobriety check for Mail.app

Hi everyone,
I've been asked at work if it is possible to add this functionality to Mail.app, in a similar vein to what Gmail has recently added to their service.
In a nutshell, what I need to create is an alert dialog that pops up when a user clicks the send button in Mail that allows them to confirm they want the message to be sent. It's not really a sobriety check (at least I hope not) but really a chance for an employee to avoid mistakes in their email message before it goes out.
At this point I'd just like to know if it's feasible before I go down this route and if anyone has any advice for an AS noob looking to do this. Bonus points if you know whether it's possible to add a modifier to the Send button to bypass the script.
Thanks much!

Not directly - at least not via AppleScript.
Mail.app supports AppleScripts for scanning incoming mail messages. There is no support for AppleScript on outgoing messages.
It is possible to write Mail.app plugins, but they're not well documented (search for 'Mail.app plugin' for an idea) and requires an understanding of Objective-C.
The last option I can think of is to not use Mail.app's automatic send/receive. Instead using a stay-open AppleScript to periodically get mail and check for messages in the outbox. If it finds any it posts the question then sends the message(s). The problem with this approach, though, is that it's far from foolproof (the user can send the message manually by enabling automatic mail sending).

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