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I've a network topology on Azure which looks like this:

Virtual Private Network A:

  • address 10.0.0.0/16
  • Gateway:
    • GatewaySubnet: 10.0.1.0/24
    • Public IP: dynamic
    • Client IP range: 172.16.0.0/24

Virtual Private Network B:

  • address 10.1.0.0/16
  • Gateway:
    • GatewaySubnet: 10.1.1.0/24
    • Public IP: dynamic
    • Client IP range: 172.16.1.0/24

They are both connected to each other using site-to-site connection. I could login to one of the Virtual Machine from VPN_A and I can ping VPN_B.

The problem occurs when I'm logged in remotely and connected to VPN_A using VPN connection. At this stage I can ping machines from VPN_A, but I cannot ping VPN_B.

Could you help me and point out what are the options to achieve this ? Is there a way to redirect my request, so if I'm connected to VPN_A only and I'll send request to VPN_B, it will know somehow that this request must travel:

  1. From local machine to VPN_A
  2. From VPN_A to VPN_B
  3. From VPN_B back to VPN_A
  4. From VPN_A to local machine

Thank you for help

My VM are using Ubuntu as operating system.

For site-to-side connection I was following Microsoft Azure documentation (https://azure.microsoft.com/en-us/documentation/articles/vpn-gateway-create-site-to-site-rm-powershell/) so from my understanding I've created IPsec IKE S2S VPN tunnel between my two gateways using their dynamic public IP address.

For client-to-vnet connection I was following this documentation: (https://azure.microsoft.com/en-us/documentation/articles/vpn-gateway-point-to-site-create/), so I think it is P2S SSTP tunnel from my client to VPN.

  • NAT is like violence: if it's not working, you're probably not using enough. – womble Jul 7 '16 at 8:23
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Right now in Azure there is no way to route traffic the way you described.

You can either create a site to site link to each vnet (or a point to site connection for testing)

You can invest in an Express route connection and use MPLS to swap routing information

You could consider using one Vnet with multiple subnets instead of two Vnets, unless you have created them in different regions for a reason not mentioned above.

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