Chained RDP over chained VPN

Chained RDP over chained VPN
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Subject Author Date
Chained RDP over chained VPN Frank Winkler 06-19-2008
Posted by Frank Winkler on June 19, 2008, 8:47 am
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Hi there !

One of my colleagues has a very strange problem. He asked me to help him as
I'm the infrastructure and networking guy but I'm quite sure that this is
not a Cisco problem but rather a Billy-OS one.

From home, he RDPs to a machine in the company LAN over a VPN tunnel.
There he opens a second VPN connection (onboard PPTP) to a customer site,
and as soon as he tries to start a second RDP session to a customer
machine, the Cisco VPN tunnel breaks down. The same thing worls without the
first VPN tunnel, i.e. from a client inside our LAN.

Any ideas?

TIA

        fw

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Posted by artie lange on June 19, 2008, 9:02 am
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Frank Winkler wrote:
> Hi there !
>
> One of my colleagues has a very strange problem. He asked me to help him
> as I'm the infrastructure and networking guy but I'm quite sure that
> this is not a Cisco problem but rather a Billy-OS one.
>
> From home, he RDPs to a machine in the company LAN over a VPN tunnel.
> There he opens a second VPN connection (onboard PPTP) to a customer
> site, and as soon as he tries to start a second RDP session to a
> customer machine, the Cisco VPN tunnel breaks down. The same thing worls
> without the first VPN tunnel, i.e. from a client inside our LAN.
>
> Any ideas?
>
> TIA
>
> fw


On the properties of the PPTP connection, goto the networking tab,
double click the TCP/IP option, goto the advanced option, and ensure the
use default gateway on remote network is unchecked.




Posted by Frank Winkler on June 19, 2008, 10:08 am
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artie lange wrote:

>On the properties of the PPTP connection, goto the networking tab,
>double click the TCP/IP option, goto the advanced option, and ensure the
>use default gateway on remote network is unchecked.

We'll try that - I forgot to mention that I have no clue of Billy-OS ;) ...

But what's the connection between the default route on the "hop" system and
the breaking VPN tunnel?

Regards

        fw

Posted by artie lange on June 19, 2008, 10:26 am
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Frank Winkler wrote:
> artie lange wrote:
>
> >On the properties of the PPTP connection, goto the networking tab,
> >double click the TCP/IP option, goto the advanced option, and ensure the
> >use default gateway on remote network is unchecked.
>
> We'll try that - I forgot to mention that I have no clue of Billy-OS ;) ...
>
> But what's the connection between the default route on the "hop" system
> and the breaking VPN tunnel?
>
> Regards
>
> fw

By enabling the default route on the PPTP connection, all traffic is
routed over the VPN ,thus breaking your IPSEC VPN.

Google split tunneling.

Posted by Frank Winkler on June 20, 2008, 4:02 am
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artie lange wrote:

>By enabling the default route on the PPTP connection, all traffic is
>routed over the VPN ,thus breaking your IPSEC VPN.
>
>Google split tunneling.

Aaah, of course, I know spilt tunneling - but I didn't fully understand the
wording of that option and what it does in fact. If M$ called it "split
tunneling", I would have known what's going on :) ...

Other good news: it works now. And now that the above clarified, things
make sense. Thanks for your hint!

Regards

        fw


other useful resources:
The Federal Communications Commission (FCC)
Telecommunications Industry Association
Electronic and Software Security Products and Services
International Telecommunication Union

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