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Outlook will not Send/Receive emails via exchange through VPN


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
2 Solutions
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?
Sam PanwarSr. Server AdministratorCommented:

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 .

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.
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oasistechnicalAuthor Commented:
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?
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?
oasistechnicalAuthor Commented:
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?

oasistechnicalAuthor Commented:
Something interesting now, i installed a SSL certificate and exchange works via the VPN now but not without VPN.

Try to reconfigure the outlook profile, if not success please provide the error message.
oasistechnicalAuthor Commented:
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, 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 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?

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.

oasistechnicalAuthor Commented:
After viewing TCP viewer, i did the below.

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


So can award points to subsun for pointing me in the right direction.
oasistechnicalAuthor Commented:
Problem solved as per above
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