Hi all, and first forgive me if I've missed something on the site, rules or the proper place to post, this is my first question here, and would like to start of by saying thank you for the chance to ask here, and that I have read a lot here in the past.

Here’s my situation, I need to configure the SBS 2003 exchange SMTP connector to route all outgoing emails from one local user, which is the owner of the business, out through the SMTP connector. By default, I know that internal email from local AD users never gets routed externally, it gets there immediately, without leaving the domain, which makes sense and saves time, however this imposes a slight problem for this user: it prevents local user A from seeing any messages sent from local user B externally on the ISP, I know it seems silly to do this, but this customer has reasons of why they wish to check there mail there, I know OWA could help the issue a lot, but he does not like it period, so makes my life hard in return, not to mention he uses a Treo, windows based and want use OMA, nor purchase a certificate, so that it can be done the right way, well one right way I suppose. Yet he swears by knowing more about security than anybody. So short of adding a POP account for sending his mail, I’m stumped as to what to do next, and I didn’t really wish to take that route anyways. I would like if possible for Exchange to send the message out to the internet then back in for every email, and it doesn’t need to be limited only to his account, if there is a better solution available, besides the ones I’ve already tried pushing for already, which is OMA, and OWA.
However, if it’s any help, here is some info that might be needed: for all incoming mail I use a pop-connector, pulling down mail, leaving a copy, so that the Treo receives mail there like it always has done, so does his outlook at home pull a copy, and every day or so he logs in and deletes the mail from the ISP (webmail account), his so called reason behind this is that he can get messages on the webmail, from internal users which like stated earlier could be done through OWA, but that is my situation. I was thinking there must be a way to disable the internal mail from staying inside, or stop it from searching for the .local and sending internally. Or is it a solution to change the AD email account so that it reflects another email account for internal users only, such as user1@gmail.com , for example and forward all mail received here to the ISP, and receive as normal through the pop-connector, but then I wonder if this will cause a problem for him sending mail out, would this type of change affect the default account for sending emails.

I have thought long and hard, done research, and thought just maybe, it’s time for some help; any suggestions would be great.

Thanks in advance.
Bradley