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Send email from Outlook Express through Exchange server from outside of domain

Posted on 2007-11-28
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Last Modified: 2008-02-01
I have an Exchange Server running on a MS SBS 2003.  I have a user that will need to use Outlook Express to send and receive mail from outside the domain.  I have it configured and working for this user to receive, but I cannot send email through Exchange.  I know it's has to be something I am missing on configuring a user to send email through Exchange when not in the building.  At the same time, I do not want to create an open-relay.  Any help on this would be greatly appreciated.  Thanks.
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Question by:steyerhuber
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Expert Comment

by:bhnmi
ID: 20367032
in the OE settings for that account, make sure you have outgoing server requires authentication is checked and set to use the same credentials as the incoming server. Then you need to open port 25 to the exchange box and make it available to authenticated user. You do this from the System Manager on Exchange by right clicking on the SMTP server and on the access tab click relay restriction. Here you will see a check box on the bottom to allow users that authenticate.
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Expert Comment

by:ormerodrutter
ID: 20367034
You cannot use Outlook Express with Exchange full stop.

If you want your user to be aable to do email outside the office you have 3 choices:0
1. OWA - Outlook web access (easiest)
http://en.wikipedia.org/wiki/Outlook_Web_Access
2. VPN - Virtual Private Network (requires some networking knowledge)
http://www.howstuffworks.com/vpn.htm
3. RPC over Https (User uses Outlook to do email just like the way they do in office, but require registry change)
http://www.msexchange.org/tutorials/Outlook_2003_Connect_Exchange_2003.html

If you use Outlook Express you can only send/receive via individual POP3.IMAP account.
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Author Comment

by:steyerhuber
ID: 20367319
bhnmi...

I have those already configured and it does not work.  Receives great.  Just cannot send.
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Author Comment

by:steyerhuber
ID: 20367333
ormerodrutter

What if the user uses Outlook 2003?
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Expert Comment

by:bhnmi
ID: 20367339
Telnet to your public IP address on port 25

>telnet x.x.x.x 25

What response do you get?
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Author Comment

by:steyerhuber
ID: 20367404
bhnmi

I blank screen
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Expert Comment

by:bhnmi
ID: 20367411
Restart the SMTP server and try again. Look for anything in the system logs also. Try again with the internal IP also and see what happens.
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Author Comment

by:steyerhuber
ID: 20367450
Same results.  When I use the Air Card and try to send mail from the outside, i get the errors.  If I connect to the Internal network and change the server name for incoming and outgoing servers to the server name, it works perfectly.
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Accepted Solution

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bhnmi earned 1500 total points
ID: 20367622
Open up the relay settings by relaxing the security. See if you can telnet in from the public interface then. If you can we can start locking it down from there.
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Expert Comment

by:ormerodrutter
ID: 20372385
steyerhuber,

I think I have misread your question - so your use wants to use OE to receive email outside of your own domain?

If you want him to be able to send through Exchange while in the building the Outgoing server must be set to your Exchange server and checking the Outgoing server requires authentication box. You need to enter his Windows logon credentials which are different to his incoming server.

But this won't work when he is not in the building, simply because when he uses network elsewhere, the network won't know about your Exchange server. So in that case you still need either VPN or RPC over HTTP setup.
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