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On Prem AD connected to Azure AD connect. A vendor we are using requires an IPsec tunnel to a DC on their side to then create a trust to our on Prem AD. Problem is, their router is not compatible with ours due to them being behind a NAT and refusing to use OpenVPN.

I already have a tunnel from our On Prem DC to Azure AD, which works. I added another connection to the same VNet to our vendor. That’s up and connected. I can ping and RDP into the machine they setup. There are no pings or RDP to our on Prem AD. Can this work? I just need both connections to communicate with each to allow our DC to communicate with their VM. The vendor won’t help for anything, mostly because I don’t feel like he knows how to do it.

Appreciate any help.

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