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Outlook via VPN

Posted on 2010-08-26
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Last Modified: 2012-06-27
Hi All!

Got a guy on a SBS 2003 network - everything is fine.  

Now, he needs to connect to an exchange server on another network across the country via VPN.  When I setup his laptop he was local to that "new" exchange machine (visiting the place and his laptop was on their network), so I setup a new profile in outlook, Bingo...life is beautiful.  

Now, he's back in his city and VPN-ing into the network and when he uses the new profile it connects fine and he's able to receive mail, but when he tries to send, he gets a bounceback that says:

There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator 554 relaying denied

Now, i know there's nothing wrong with the "Recipient's email server" - I tried a dozen different addresses and got the same result - so it's obviously an issue coming from the "new" Exchange machine.  

Any idea on what's happening here?  Is it seeing and reacting to the external IP on the VPN?  I'd like to have some suggestions before I talk to their part-time IT guy.  Any thoughts/suggestions appreciated!


Thanks!
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Question by:markhaase
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Accepted Solution

by:
Fayaz earned 167 total points
ID: 33535221
If only for email, there is no any need for VPN, please visit below link for more info;
http://www.msexchange.org/tutorials/outlookrpchttp.html
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Expert Comment

by:davenport651
ID: 33535232
The Exchange Server must be seeing this computer's external IP address (like some stranger on the internet) rather than their VPN'ed local IP.  Check the IP address settings on this computer to verify that it has an address on their local network.  Also verify that you are only sending data to the VPN and not out to the internet.
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Author Comment

by:markhaase
ID: 33535251
---> f only for email, there is no any need for VPN,

Forgot to mention....the VPN is not only for email - there will be file sharing down the line...Thanks!
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Expert Comment

by:BLangers
ID: 33535269
Since you get an SMTP error, I presume you have setup a POP3/SMTP e-mail account in Outlook to connect to the exchange server on the other network. You should setup an Exchange account. If you are not using Outlook 2010, you will need another profile since you can only add one Exchange account per profile in outlook pre-2010.
If you are using a POP3/SMTP acount, the SMTP server you need to use will depend on the Internet connection you are connected to since nearly all ISPs block access to their SMTP servers from a 'foreign' network.
You *can* use the SBS server as SMTP server if you are connected via VPN, if you choose to authenticate to the SMTP server and use a domain user account to make the SMTP connection to the server.
Hope this helps
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Author Comment

by:markhaase
ID: 33535294
--> Check the IP address settings on this computer to verify that it has an address on their local network.

Yup, it does

--> Also verify that you are only sending data to the VPN and not out to the internet.

Well, Outlook is connecting  to that specific Exchange Server, which it can only get to on that network.  Is there another way to lock that down?
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Author Comment

by:markhaase
ID: 33535358
--->I presume you have setup a POP3/SMTP e-mail account in Outlook to connect to the exchange server on the other network. You should setup an Exchange account.

No, strangely, it IS an exchange account.  I was a little curious about the SMTP error also.  I can setup a fresh exchange account from here (i'm in yet a third city) and during the setup it resolves the server name and user name just as you would expect.  I've been able to share calendars with other Outlook users, etc, and other than the sending error, it's a good solid Outook/Exchange connection.  

I wonder if he (the part-time IT guy) is using a smart host that's bouncing stuff back to me.  Maybe I just have to call him.

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Expert Comment

by:davenport651
ID: 33535592
Check the Outlook "Account Settings" (Tools - Account Settings) and make sure the exchange account is the only one listed (or that's its Set as Default).  It seems like, for whatever reason, Outlook is attempted to send to an SMTP server.
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Assisted Solution

by:BLangers
BLangers earned 166 total points
ID: 33535798
if you get an SMTP error from an Exchange account, it is indeed not your Outlook profile that is causing the problem, but something in the configuration of the Exchange server... Can you send messages to internal recipients on the same Exchange organization? Are there any other accounts in the Outlook profile?
Do you get the server generating the error in the SMTP error message? The exact source will be visible in the message tracking center on the server, but you'll need access to the server for that...
If it is a server error however, you should not be the only one getting the error message, it should affect everyone...
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Author Comment

by:markhaase
ID: 33547699
--->  Can you send messages to internal recipients on the same Exchange organization?

Excellent question....don't know...will have to check.


---->  Are there any other accounts in the Outlook profile?

Nope, Just Exchange.


----> If it is a server error however, you should not be the only one getting the error message

True, but I think my client is the only one connecting via VPN.  It's my understanding that they set the VPN  thing up just for him.  Everyone else works locally at the office.  He's 1500 miles away.


----> you'll need access to the server

Bingo.  Looks like I just have to call the guy.  I was hoping to have some real idea of what was going on first, but without the answers to certain questions that only he can give me, it looks like I'm kinda at  dead end.
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Assisted Solution

by:davenport651
davenport651 earned 167 total points
ID: 33559652
The VPN software that my company uses has a check box to explicitly allow or disallow local network access after a VPN has been established.  I'm not sure how the routing is done, but if this check box is active then packets which SHOULD be going through your VPN might be going unencrypted through the internet.  On the Cisco VPN software, this setting was found when I modified the connection settings.  This is the only other thing I know of which could be causing this issue solely for an offsite person.
CISCO-VPN.jpg
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Author Comment

by:markhaase
ID: 33871782
Have received ZERO coperation from the admin of the exchange server in this case, so i'll have to close this and move on - thanks everybody for the suggestions...

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Expert Comment

by:Fayaz
ID: 33873197
So many efforts and it cannot be simply discarded; Points should be allocated to relevant answers and experts.
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Author Closing Comment

by:markhaase
ID: 33880815
Can't solve the issue since exchange admin will not co-operate.  Points distributed to all who participated.

thanks!
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