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Edit: I did cleaned up the question to focus on the main and more urgent problem to solve.

I create a site-to-site VPN on Azure, and connected it to a virtual machine hosted in our server room in the office.

There is another VM in the office that connects to a client VPN. This is using Tosibox, and it requires a hard token, so there is no way to move it to Azure.

The problem I'm having is that I need from within Azure to be able:

  1. To route the traffic to client IP address through Azure virtual network (solved, it is in the config available in the Azure portal)
  2. Once the request comes in the office, route it to the client VPN.

I'm in no way a network admin or anything so if there is somebody who can provide some hints, that'd be nice. Thanks.

Edit 2: More details:

Different endpoints:

  1. Azure-VN: Azure Virtual Network
  2. Azure-Machine: Machine hosted in the Azure VN
  3. Office-VPN: Virtual machine hosted in the office that is the point of contact of the Azure VN
  4. Tosibox-VM: Machine hosted in the office that has the Tosibox VPN and thus the Tosibox Key (needs to be a different machine as only 1 Tosibox Key is allowed per Machine and we have to support multiple keys)
  5. Client: Client machine where I need to connect

Current Situation:

The site-to-site is working as:

  1. Azure Portal has all things green
  2. From Azure-Machine I can ping/contact Tosibox-VM
  3. From Tosibox-VM I can ping/contact Azure-Machine

The Tosibox VPN is up and running. All is green in the client and I can get to the data I need from Tosibox-VM

So now, I can do this:

From Azure-Machine: PING Tosibox-VM

From Tosibox-VM: PING Client

What I need to do:

From Azure-Machine: PING Client

Additional Information

There is no hardware involved in the setup of the Azure VN. Only Tosibox has a hard token, though the VPN is software based as the token is only used for encryption.

Mike Sherrill 'Cat Recall'
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Georges Legros
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    This question has far to wide a scope to be dealt with here, especially in its current state. – Patrick Oct 08 '15 at 13:50
  • I'd be happy to reduce scope or focus on specifics, I'm just trying to give as much context as possible to avoid solution that could close the doors for the entire goal – Georges Legros Oct 08 '15 at 13:52
  • Just edited the question, I hope this helps getting valuable answers – Georges Legros Oct 08 '15 at 19:13
  • Can you add a little more details describing the current topology? The Azure -> Office VPN. Where does that terminate? Is that the same router as the your office -> client VPN? If not what is the potential route that traffic would need to take to get Azure -> Office -> Office -> Client? Can you include the hardware that you have that comprises the network you wish to configure? – Patrick Oct 09 '15 at 09:45
  • Tell me if this is enough or if you're still missing some informations – Georges Legros Oct 09 '15 at 10:07
  • @GeorgesLegros: How did you resolve this problem? – Mike Sherrill 'Cat Recall' Mar 14 '17 at 16:09

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