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Outlook access over Site to Site VPN Tunnel

I have a VPN tunnel created over an ASA 5510. We are not doing any NAT'ing and allowing all subnets from both sites to communicate with each other. Only issue we are having is users that have VPN Client on the remote side are not connecting/communicating with the exchange server. We are restricting the use of services on the Hub side of the VPN tunnel. I've allowed all ports used by exchange such as IMAP, POP3, RDC and SMTP.

Are there any other ports that we need to allow.


Super Bronze

Outlook access over Site to Site VPN Tunnel


You mention that you have a L2L VPN from the Remote site to the rest of the network?

You also mention that the Remote site also has a VPN Client connection?

Have you configured the Remote Site ASA so that the VPN Client traffic can actually enter the ASA and enter the L2L VPN connection?

This usually requires additional configuration for the traffic to be able to enter through a VPN connection and head out through another VPN connection.

- Jouni

Community Member

Outlook access over Site to Site VPN Tunnel

So I have a site to site VPN tunnel with us and another customer. They have users from our company at thier location. They control thier own Firewall and location. We just route thier subnets and they do the same and route ours. We orginally had our VPN traffic going over a 3030 concentrator and migrated to ASA5510. All they did on thier end is change the Peer address.

Our side we created service objects and allow all traffic they need access too. https, dns, smtp etc. They are using Microsoft Outlook client on thier end since those users belong to our company but hte Outlook client will not connect to our Mail server on our side of the tunnel. We have verifed DNS and they can Ping our servers. Was hoping someone would know what ports I need to very and make sure are open to allow traffic.

Outlook access over Site to Site VPN Tunnel

Oulook what kind of email u re configuring on Oulook Gmain/Hotmail/Yahoo everyone has differet smtp and pop ports.

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