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Cannot send email with outlook when connected to cisco VPN

when using Cisco VPN client version 4.6.02.0011(transport IPSec/TCP) I cannot send emails via outlook 2003 SP3. I can recieve emails fine though. I also cannot reach some of my internal work websites. I do not experience this issue when connected via another network/aircard/hotspot/etc.. This problem has been present since FIOS was installed and everything worked fine before FIOS. Please help me out.

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dslr595148

What is the ISP of the VPN Server ( Is it, Verizon ) ?

ravioli

Since almost all IPSEC VPN implementations for client VPN use a mode which encrypts the entire packet -- including the packet header -- there is nothing that Verizon can be doing to detect your "mail" traffic from any other traffic headed for your corporate VPN. It is, simply put, all encrypted. It doesn't hurt however to double-check with your network administrator to make sure that is truly the case.

If you couldn't make a connection at all for the VPN itself, then I could maybe give you some parameters to tweak on the Cisco client to make sure you are using the mode best suited for a NAT traveral scenario.

Other thing to ask your administrator is if the data path for the SMTP traffic from the client to the serer is "inside" the tunnel or "outside". There are ways to figure that out yourself if you have the IP address of the mail server and run a few commands on the client, but as I not longer use a Cisco client, I'd have to research that further to tell you where to poke. If the answer to this question however is "outside" -- there's your problem. You've met the Verizon blocks SMTP port 25 traffic from clients issue which has been discussed adnauseum on this forum.

-- ravioli (aka "lasagna" who is presently having an "out of userid" experience thanks to a Verizon "upgrade")

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