VPN Connection - problem?

[Beetnik]

Using 1) Outlook for mail and it syncs to mail provider (1and1) via ISP (Bethere) and a 2) secure VPN connection to access a database on someone else's system.

I've been getting complaints that Outlook won't send mail and, whilst I've tried altering a few settings, repair etc the problem continues.

Have now figured out that it only seems to happen when the VPN connection is open. Is this a coincidence or an inevitability and if the latter is there a fix?

 

[moonloops]

Most VPN's disable all other connections (such as to internet) as a security measure. (Stops nastys traversing from internet to corp network). You can disable this if it is a typical software VPN.

 

[Dryce]

Have now figured out that it only seems to happen when the VPN connection is open. Is this a coincidence or an inevitability and if the latter is there a fix?

Moonloops is probably correct if you're using a corporate VPN connection.

However it might just be down to change of routing or DNS. So that there are being directed via the VPN to the corporate network instead of the net.

 

[Beetnik]

It's a very large corporate network and they're paranoid about security so I guess we'll just have to disconnect when the time comes for email.

 

[Sanj]

When you go through a VPN you route all traffic down the tunnel, there are exceptions to this if you have split tunneling enabled on your vpn client.

Your request is probably being blocked by the corporate firewall (mail runs on port 25/tcp)
By design you would only allow your mail gateway/ and or exchange server outbound access on port 25.

Speak to the firewall guys to see if they can see port 25 being blocked on the firewall?

 

[Sp!ke]

What VPN software are you using?

Does it have an option to split tunnel and has it been turned off?

 

[Beetnik]

Software is Cisco. I'll have to look tomorrow to see if it's configurable.

I've tried using port 587 but no go.

 

[Sp!ke]

Cisco VPN does allow you to split tunnel although this can cause problems depending on how you set the binding order of your network adapters and where your PC resolves DNS whilst running VPN.

Highlight the VPN connection, select modify and then hit the transport tab and check to see if allow local lan access is enabled or not.

 

[Sanj]

I still think split tunneling needs to be enabled on the pix/asa as well as on the vpn profile to make this work.

 

[bolide]

How is it resolving the name of the mail server? And where is the mail server? If the mail server is on the corporate LAN you're accessing via the VPN I'd expect you to be able to see it but only if the DNS is giving up the correct address for the mail server

Try "host yourmailservername" at the command line and see what IP address comes back. Try this test twice - with the VPN connected & without

Nick Froome