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Exchange 2003 for Internal Mail / ISP for External Mail

Posted on 2009-05-11
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Need help with mobile users and domain users on laptops!

Small network running SBS2003 with Exchange 2003 handling interoffice mail, shared calendar and shared contacts. We're using NAME.com for all addresses. This is working fine- but now we have new staff that work from home or use a laptop in the office.

How can I get mail sent from the GAL to go to an external address when the user is out of the office, but send through Exchange when the user is logged on to the internal network?
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Question by:maduko
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Hypercat (Deb) earned 500 total points
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What about simply having the mobile users use Outlook Web Access to access their company mailbox when they're out of the office?  This would be a lot easier than trying to configure your system to use two different email addresses for these employees.
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by:maduko
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The users have complained about "needing two different places to check their mail" and prefer to just use Outlook. Plus I have been reluctant to open up the network to the outside world for OWA.
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by:Hypercat (Deb)
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OK - although OWA is quite secure when using the self-signed SSL certificate that is automatically created when you set up OWA and/or RWW in SBS.  If they don't like OWA, you could have them use RPC over HTTP instead.  Here's an article on how to set that up:
http://technet.microsoft.com/en-us/library/bb123622(EXCHG.65).aspx
Basically it's very much like enabling OWA, since you do this by running the CEICW to create an SSL certificate and enable RPC over HTTP.
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by:maduko
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Right now I'm testing a server side rule that forwards to the external address. That works pretty well except you have to remember to turn it on when you leave the office!
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by:Hypercat (Deb)
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Yes, exactly what I was thinking. I was going to suggest that, but it's a bit clumsy, and also it could cause problems if the user replies to an email that was received as a forward from an external email address.  The next mail that that client/outside contact sends to that person may go to the external email address instead of to the company email address, and that could get messy as well.  That's why I was trying to suggest alternatives that would keep the same email address whether they were in or out of the office.
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by:mds-cos
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Sorry, but I need to weigh in here that you are GOING THE WRONG DIRECTION (sorry to yell).

The correct answer is as given by hypercat already.  User RPC over HTTP for users that have laptops.  It is secure and works fantastically.  Use OWA for users who do not have a company laptop.  Users only look for e-mail in one place (their inbox), you keep company e-mail where it belongs (in your company controlled systems), and you don't create a support nightmare when something happens outside your network.

Reasons you positively do not want to forward e-mail to personal POP accounts:

1)  E-mail often contains proprietary company information.  Forward it and you just sent your proprietary and confidential information out over the Internet in plain text and to servers over which you have no control.
2)  E-mail is part of the company identification.  People are going to start replying to e-mail from their personal accounts...what will your customers think about this?  Does a company really want it's employees doing business from mycoolemail31@hotmail.com????   No.
3)  You totally loose control of the company asset knows as e-mail.  Think about what happens when an employee leaves under bad circumstances.  They have all of this company e-mail sitting on their home computer, and all of these company contacts used to corresponding through the personal e-mail address of that person.
4)  Forwarding e-mail around the Internet is clunky, messy, and introduces more points of failure.  E-mail today is a vital means of communication, so you do not want to introduce unknown factors into it.
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