If the prompt is an OLE object, perhaps you can have Perl signal "OK" to the prompt. (You might also be able to remove this security restriction, but I doubt it.)

Furthermore, I would also like to display this information to a webpage (IIS Web service running as me w/ Admin rights). For some reason whilist browsing this script via browser (with added 'Content-type' etc, etc..) The script Just hangs and I don't get the warning prompt as I do when running the script from the command line. Any thoughts?

Could the problem be that the script running through the Web server cannot open the outlook application (thus, no warning prompt)? Are you working with an Exchange server? If you are, you probably have Outlook Webmail installed. You could have Perl login to Webmail, grab the contents of your inbox, and spit it out for you as a webpage. Or you perhaps could tell Exchange to publish your inbox as a webpage. I often see this done for calendars, but I am not sure if you could also do this for inboxes as well.