I need a method to prevent the sending of an email or at least present a warning to the user if an attachment doesn't meet certain criteria. In short, I want to safeguard personal information. Here is the scenario:

• I have a Word document named "Tom Jones Personal Information". It contains personal information on Tom Jones.
• I need to email this document to Tom Jones, plus CC a few others.
• I need a check to prevent, or at least warn and cancel, the sending of the email if some criteria is not met.
  • One thought is that "Tom Jones" must be present in the Subject line, else the sending is cancelled or the user is warned and can cancel the sending.
  • Another thought is that "jones" must be present in the email address, else...

You get the idea. I'm open to strategies other than the ones I described. I was thinking that perhaps an Outlook rule could be created to do this, but I'm not finding a way to make that happen. The crux of the matter is that I need a method that helps assure the correct attachment is going to the correct recipient. Any guidance on this will be greatly appreciated.

I'm using Office 365.

Thanks in advance,
Andrew