can not connect/ping to any computer that has TMG 2010 as its default gateway across VPN(LAN)

Hi all,

basically, im on the range which is part of our vpn network
im trying to ping/rdp to a computer that is on the network

the TMG 2010 server is on i can ping/connect to that server and any machine that doesnt have as its default gateway

any machine that has as its default gateway cant be reached
on the TMG server RRAS ive added static routes for all my internal networks
so the TMG server can ping all my internal ranges fine

i think its got to be something to do with the default gateway

TMG's external card is on so all traffic goes out of
the static routes work fine i can now verfiy

im rdp'd to a machine that does not have its DG as and then from that machine ive rdp'd to a machine that does have its gateway as 101.10 and from there i can ping fine

so its not routing, ive also created a rdp policy and a ping polcicy to allow it for all networks and ive added all the interal ranges to TMG

can anyone shed any light? im baffled!
Who is Participating?
Bruno PACIConnect With a Mentor IT ConsultantCommented:
So... I'm now supposing your schema had an error and the IP address on ROUTER 1 in instead of

The location of the TMG server in your network is not really clear... What exactly do you want to use TMG for ??? Do you want to use it to manage traffic going to Internet only ? And in this case what sort of protocols do you want to manage ? Web only (http, http, ftp) ? Any other ?

If you want to use TMG to manage all outgoing traffic from your internal subnets and then why is there an direct Internet connection on ROUTER 2 ?

If you want your TMG to be a Web Proxy server only then the best solution is to remove one NIC and leave only ONE NIC on TMG. For Web traffic to pass through TMG you'll then have to declare its IP address as the proxy in Internet Explorer configuration on your client computers.

If you want TMG to manage any traffic going to Internet then its location is bad: you can not force traffic from outgoing to Internet to pass through TMG because ROUTER 2 has a network interface directly connected to Internet and then will route outgoing traffic via this interface.

If you want TMG to manage traffic going to Internet from only then the best location is between ROUTER1 and Internet.

If this location is not possible because you can not change anything on ROUTER1, or if you don't want to change location of TMG, the only solution to make the whole thing work is to make a specific IP route configuration on client computers of subnet by doing this:
1) Declare the IP of TMG ( as the default gateway in the TCP/IP configuration of each client computer in subnet
2) Add the following static IP route on each client computer of subnet using this command: ROUTE ADD MASK /P

Configured like that, client computers of subnet will send all IP packets for to ROUTER 1 that will transmit them to ROUTER2 to reach the destination. TMG will not be involved in dialogs between and
To reach any other subnet than and, client computers will send IP packet to TMG (as it is their defauly gateway). TMG will manage the packets and will block or allow them depending of its firewall rules. Of course, TMG must be configured so that its default gateway is ROUTER 1 (

Have a good day

Bruno PACIIT ConsultantCommented:

ISA/TMG server will NEVER let pass a IP answer packet to a IP query that did not already pass through ISA/TMG server... Let me explain what I suppose happens for you :

From a computer C1 that is on a subnet A you ping a computer C2 that is on subnet 2... computer C1 uses a default gateway G1 that is not the TMG server... computer C2 uses the TMG server as the default gateway...

From computer C1 you make a PING C2.
An ICMP query packet goes out from C1 and is given to the default gateway G2. As G2 is a simple routeur it transmits the ICMP query to the subnet B and the packet reaches computer C2.
Computer C2 then replies with a ICMP response. AS TMG is the default gateway this packet is sent to TMG.

TMG receives an ICMP response that doesn't match with any ICMP session that TMG knows... Because the ICMP query never pass through TMG. TMG is not a routeur, it is a firewall ! That means that it will verify any packet that is given to it and its job is to drop any unknwon packet. In your case the packet is unknown because TMG can not understand to receive an ICMP answer without any ICMP query before.

that explains why C1 never receives the ICMP answer to the PING command.

Now, why does it works from C2 pinging C1 !? Explanation:

C2 sends an ICMP query to C1 via the default gateway TMG.
If there is a rule in TMG that allow ICMP between subnet 2 and subnet 1 then TMG let the ICMP packet go through... TMG also memorize that an ICMP dialog has been initiated and expect to see an answer coming back in the following seconds.
Anyway, the ICMP query reaches C1 that answers with an ICMP response. This ICMP response is sent to C2 via G1 gateway.
As G1 is a simple "stupid" routeur it's job is to pass network packets from one subnet to the other without looking at what these packets are for.
So... G1 makes its job and transmit the ICMP answer packt to subnet 2 to C2 computer..

C2 computer receives the ICMP answer and then display "Successfully pinging C1... echo reply".

Meanwhile... TMG expect the ICMP answer to come back and is ready to let this asnwer pass as TMG knows that an ICMP query as been initiated. Unforntunatly, the ICMP answer will not come back through TMG because C1 is configured to use another gateway...
The poor TMG server waits and waits for a while (around 30 seconds) and finally suppose that the ICMP target is dead or any... anyway, TMG will the decide to stop waiting, will erase the ICMP dialog for its memory and will probably write something in its log saying "Session closed (timeout)".

The morality is that, if you want things to work well with TMG you must ensure that your IP configuration on client computers is "normal" and that is query packets have to pass through TMG then the IP route back must also pass through TMG...

Have a good day.

awilderbeastAuthor Commented:
ok i follow you now

how can i get round it?

create routes on my router so that all traffic destined for the 101.0/24 network goes to the external interface of the TMG server 200.1, if i did that would the TMG server know what to do with the traffic?

Free Tool: ZipGrep

ZipGrep is a utility that can list and search zip (.war, .ear, .jar, etc) archives for text patterns, without the need to extract the archive's contents.

One of a set of tools we're offering as a way to say thank you for being a part of the community.

Bruno PACIIT ConsultantCommented:

Well, the best way is to not put the TMG as the default gateway on your client computers. Make them use your usual router (let's call it ROUTER1) that links subnets and 102.0...

The route to go to (what is behind your TMG if I understood well) via TMG should be added in the IP route table of your router ROUTEUR1.
So... All client computer that need to reach a subnet that is not its own subnet will send IP packets to IP routeur ROUTEUR1.
ROUTEUR1 will use it's route table to transmit the packet: if the packet is for then ROUTEUR1 delivers it on its 192.168.102.x interface, if the packet is for the ROUTEUR1 transmit it to the next routeur that is TMG TMG will then make its job with this packet...

You have to make things the simpliest so that your usual IP routeur is the central point for any trans-subnet packet. Doing like that you ensure that TMG will only be involved in internal-external traffic and not in internal-internal traffic.

Have a good day.
awilderbeastAuthor Commented:
ok  i get that now thanks

what do you suggest as a solution? alter my routers routing table?

send all packets destined for the network to tmgs internal interface and then tmg wil know what to do with the rest?

Bruno PACIIT ConsultantCommented:

In my opinion, the best way if to alter your routing table.
If you want to pass through TMG for all network traffic between and you'll have to create so much rules to allow normal traffic between these subnets that you will probably give up and create a unique rule allowing ALL traffic between these subnets... And then what is the intesrets to have a firewall on the way if it allows all traffic ?

If I have understand well these 2 subnets ( and al internal networks !? Do you really want to restrict network traffic between them ? If not, avoid to have the firewall in the middle of the path, instead go through your routeur.

You'll pass through your firewall only for traffics going to subnet and others. For that you have two options:
1) configure a static route on all your computers so that traffic to is transmit to the TMG server.
2) don't touch IP routes on computers but instead add the IP route to your routeur, which is the default gateway fol all your computers.

Have a good day.
awilderbeastAuthor Commented:
i cant think how to avoid having the firewall in between the 2

my network goes as per screen shot

Bruno PACIIT ConsultantCommented:

ok... to be sure of what we are talking about, I modified your schema addind numbers to routers

By the way, are you sure of the IP address on ROUTER 1 ??? Isn't it !??

Question has a verified solution.

Are you are experiencing a similar issue? Get a personalized answer when you ask a related question.

Have a better answer? Share it in a comment.

All Courses

From novice to tech pro — start learning today.