Messages stuck in outbox for traveling MS Exchange users using 2 profiles and 1 pst

I have recently implemented Exchange 2003 and am now experiencing a problem with our users who travel.  Messages are getting stuck in the Outbox.  The way I have them configured is like this.  I have two profiles setup in Outlook.  One is "In Office" and one is "Out of Office".  Both profiles are pointing to the same PST file.  The "in office" profile is using Exchange to send and receive.  The "Out of Office" profile is using POP/SMTP to send and receive.  Both profiles are using the same PST file to deliver mail to.  They have no problems when in the office and using Exchange.  The problem comes in when they are traveling and sending out email using SMTP.  They can send out 70% of their emails without a problem out of the office.  The other 30% get stuck in the outbox.  Once they come into the office they can switch to the Exchange "in office" profile and send and maybe 1 or 2 will go out.  The rest have to be deleted and recreated.  

In testing a few things I noticed that if I open up the POP account while in the office I got all of the messages to send that were stuck.  I just don't know what is causing the messages to get stuck in the first place while they are out of the office.  They get no errors sending and recieving, they just don't move.  

Any help will be greatly appreciated.
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SembeeConnect With a Mentor Commented:
If you are using Exchange 2003, then why are you using POP3/SMTP and PST files?
Furthermore, if you meet the requirements on the domain then you should be using RPC over HTTPS as a client access system. It is much more reliable and provides the user with the full Exchange feature set.

This requires Outlook 2003, which you get a license for as part of the Exchange 2003 CALs.

GlobalviewsAuthor Commented:
I have heard the opposite of RPC over HTTPS which is why we are not using it.  We are using the PST's for traveling users only because Exchange is slower over VPN especially over dial up rather than just using POP3/SMTP.  

This same setup has been used by others without a problem.  If I have to I will use RPC over HTTP, however I would like to find an answer to why my current setup is having problems first.

try increasing "Server Timeouts" in the POP3 SMTP profile and see if that will make any diffrence
GlobalviewsAuthor Commented:
No, that does not help.  Outlook doesn't even try to send them.  They are just sitting in the Outbox as if they weren't there all.  
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