I have OWA configured so that I can access my inside office email from anywhere. Here is the problem... if I have the .pst stored on the local computer, I can view all of the previous emails, shared calendar, and contacts... if I have the computer connecting to the .pst on the server, it show my calendar and contacts as such, but it does not show my email unless I have the outlook on my computer closed. How can I configure exchange to look at the .pst's on the server?

Exchange does not view PST files. OWA will only view the Exchange mailbox. If you are downloading email to a PST file, either on your server or local desktop, they will no longer be available in OWA.

Is there any way to change that?

Take those .pst messages and save them in a new folder under Inbox. Granted it adds to the total size of the mailbox but it gives access to the messages with OWA.

Our .pst is stored on the server

You will need to setup your Outlook to use Exchange instead of POP3.

Create a new profile using the Exchange connection method.
1. Either import the original PST file or
2. Open Outlook and then Open original PST data file from file menu. Copy or Move all emails from PST folders to exchange folders.

Hopefully you don't need step-by step instructions.

I want all my mail delivered to the pst on the server

PST folders can be viewed by Outlook but not OWA. You must open a new PST Data File to view a second PST File. OWA is Exchange only. Once an email is removed from the server (ie download & remove via POP3) it will no longer be visible from OWA.