For the moment I'm okay without the digital signatures and just allowing the user to manually allow the macro to run. I did a little research on the signatures and the process doesn't seem too onerous.

For my uses checking for a very specific distribution list is what I need. That is "Bob" is the distribution list, and "Personal Information Bob" is the name of the attachment and in the Subject line. I want all three to match up before the email is allowed to be sent.

Thanks,
Andrew