I setup an Azure Files storage account with Public access disabled and an internal Private Endpoint address of 10.0.0.4 and the provided PrivateLink DNS enabled.

I also have a Virtual Network Gateway with Point to Site connections using Azure VPN

If I connect to the Azure VPN from a Remote Client, I am able to PsPing 10.0.0.4:443 successfully (on why Azure decided to block ICMP that’s another irritating story) anyway the problem lies with the mapping of such storage account, my understanding is that only works with fqdn and my DNS resolution points to the disabled Public IP access, no good.

To overcome, I setup a DNS Private Resolver, this operates on a different Vnet address space (172.16.0.0/21) which has two subnets for Inbound Endpoint (172.16.5.0/28) and for Outbound Endpoint (172.16.6.0/28). Upon launching the DNS Private Resolver it gets an address of 172.16.5.4 which I can then add as DNS Server to my main VNet (where the VNG, Storage Account sits on) so that Azure VPN default to this DNS Server at the client level.

This is where my luck ends, I can’t map this drive by using either the fqdn or the PrivateLink fqdn, the DNS records in Azure do point to the Private Endpoint IP however the lack of knowing how to troubleshoot makes it difficult, I try PsPing or Ping to 172.16.5.4 and I get no replies, should I get any? I dunno. Is that interface even pingable so to speak?

I thought that the reason could be because the main vnet (10.0.0.0/16) and the DNS Private Resolver VNet (172.16.0.0/8) could not communicate being separate Vnets so I added Vnet Peering between the two.

This didn’t help either.

Any kind soul that can help fix this?