On 02/09/2011 12:01 PM, Nataraj wrote:
> I would also look at routing.   When the second vpn comes up, it may be
> configured to alter the routing table which would then try to route the
> first vpn through the second and the second through the first.

That sounds mostly right.  Many VPNs will take the default route in one 
manner or another, so the OP's PC probably ends up trying to route 
packets to the first VPN server through the second VPN tunnel.  Routes 
with one VPN usually look like:

Destination     Gateway:
local           broadcast
vpn1-server     original default gateway
default         vpn1-default-gateway

And then when the second one comes up, it looks like:

Destination     Gateway:
local           broadcast
vpn2-server     vpn1-default-gateway
default         vpn2-default-gateway

...At that point, you no longer have a route to the first VPN server 
that works, so you can't reach anything.

> Another problem is that pptp is udp only and cannot be tunneled through
> a firewall easily like openvpn or ipsec, so if there is any kind of nat
> going on when you connect through the first vpn, it won't work because
> you won't get your packets back.  If you were able to use openvpn tcp or
> IPSEC in a tcp tunneling configuration, it should work.

Actually, PPTP tunnels use GRE packets.  I can't think of any reason 
that you wouldn't be able to tunnel those, but many NAT devices 
definitely can't handle them (or can't handle more than one simultaneous 
GRE session).
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