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Outlook will not Send/Receive emails via exchange through VPN

Posted on 2009-07-01
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Last Modified: 2012-05-07
Hi

I got EXchange 2007, on Server 2008 setup with RRAS.
Clients can connect to VPN externally, OUtlook eventually says connected and when connected it will not send or receive emails. Can ping server name/ip address, played around with hosts file.

Please can somebody shed some light....

THank you
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Question by:oasistechnical
12 Comments
 
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Expert Comment

by:Nothing_Changed
ID: 24753813
are you using a VPN client on the Outlook client device, or is it on a LAN behind some sort of VPN lan to lan tunnel?
How does your outlook client refer to the server? as in, by server name only, by microsoft AD name, or by fully qualified domain name?
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LVL 18

Expert Comment

by:Sam Panwar
ID: 24753816
Hi,

Is there any error ?or please check that when you connect though the VPN then the domain name on which you are sending mail is resolve on that system .

regards,
sam
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LVL 40

Expert Comment

by:Subsun
ID: 24754099
MAPI uses RPC ports 135/TCP and 1024-65565/TCP (this is dynamically allocated). Using TCPView you can check if anything is blocked through VPN.
http://technet.microsoft.com/en-us/sysinternals/bb897437.aspx
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Author Comment

by:oasistechnical
ID: 24754205
VPN connects successfully to RRAS..

Exchange server and RRAS /AD server are on the same IP.
Connection is established using MS VPN Client, then Outlook open etc.
I can see shares on server etc and access them ok.
exchange server is set to full name.domain.

Must i run TCP view on machine or server?
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Assisted Solution

by:Subsun
Subsun earned 250 total points
ID: 24754316
If your outlook client on LAN works fine then there should not be any issue at server end. So connect the VPN try to connect the outlook client to exchange then run TCPView in client machine to see if any ports are blocked.
Was this outlook connection working?
If yes have you installed any patch or made any change recently to client system?
Are all the VPN clients having same issue?
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Author Comment

by:oasistechnical
ID: 24754478
Yes it works fine on LAN, new setup , so nothing has changed.

I see TCP view has 4603, 4593,4571,4583,4598 connected to server but 4579,4572,4573 cannot be established?

Is this where my problem is?

Thanks
0
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Author Comment

by:oasistechnical
ID: 24754644
Something interesting now, i installed a SSL certificate and exchange works via the VPN now but not without VPN.

mmmmm
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LVL 40

Expert Comment

by:Subsun
ID: 24755031
Try to reconfigure the outlook profile, if not success please provide the error message.
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Author Comment

by:oasistechnical
ID: 24755629
Ok i realised thats a DNS issue, and fixed that 1.
server name = nwssrv-jhb.nws.co.za(FQDN), outside domain is the same, but of an different ip range. I got a certificate to match that, internal IP is 192.168.0.10, external Ip is a 196.x.x.x address.

I think this is going to be a problem now, when offsite and connection via 3G or something, what dns servers is it using to lookup nwssrv-jhb.nws.co.za, coz i need that to resolve to the 196.x.x.x address and not the internal Ip, and when in side office it needs to pick up the 192.168.0.10 ip.

Thats just another question.

But i still have my original problem when conencting to vpn with outlook, it connects to exchange but will not send/receive, if i install ssl cert and setup HTTP over RPC then it will but slowly.

Any ideas, on what i can do, Exchange ports need to be opneed?

Thanks
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LVL 65

Expert Comment

by:Mestha
ID: 24759176
Remove the hosts file.
Then you just need to control which DNS servers the users get. If they are using a VPN then the DNS server should be AD integrated.

Outlook Anywhere shouldn't provide any speed differences. I use Outlook Anywhere full time, both inside and outside the office and there is no speed difference at all. Something else is wrong with your setup I fear. DNS may be a major part of it.

Simon.
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Accepted Solution

by:
oasistechnical earned 0 total points
ID: 24804841
After viewing TCP viewer, i did the below.

I replaced the the linux firewall with a Juniper Firewall and all worked well afterwards.

Thanks

So can award points to subsun for pointing me in the right direction.
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Author Comment

by:oasistechnical
ID: 24804862
Problem solved as per above
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