Hey guys,
I need to implement PGP in my business to secure emails that must the sent securely on a monthly basis. Due to the fact that humans are human and bound both by habit and to forget, I need to automate the encryption of that monthly e-mail.
I'd like to have the process be near fully automatic, such as engaged when the user types a certain message into his or her subject line of the e-mail, or when there's a couple of conditions that are met in the message. I've yet to decide what the condition will be, but I think something in the subject will do.
I'm using GPG (the freeware open-source version of PGP), which creates a plug-in button in Outlook. For the sake of testing, I've made a shortcut to that button on the ribbon on my computer only. I anticipate this being something that only some users do and other's dont, so I can't depend on the presence of the ribbon. The presence of the Add-In should be enough.

Basically, then, what I need to do is monitor all outgoing subjects. If the subject contains "Monthly Report", for instance, that Add-In button will be clicked. If it doesn't it won't. Can anyone give me a starting point? I don't expect you to do the work for me, as I know I won't learn anything, but I don't even know where to start.

I know that my users are using varied versions of Office, ranging from Office 2000 to Office 2007, so the script (or idea) will need to be cross-version compatible.

If it helps, I'm an adept VB6 developer, and have 10+ years coding. I just don't know about the VBA object library or coding convention for VBA objects. For all I know there is a simpler way to do this than with a macro.