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We've been using Azure's built-in VNet/VPN solution, with a combination of both point-to-site and site-to-site connections, and so far it's worked reasonably well. But our company is very - very - distributed, and we need to grant some remote OS X clients access to resources inside our Azure VNet. And of course, despite it being one of the top requests on UserVoice, MS doesn't support any non-Windows client in their Point-to-Site VPN configuration.

So I'm left looking for other options. One possibility, of course, would be to configure each of the remote home offices with, say, a Dell Sonicwall, and configure that Sonicwall with a Site-to-Site VPN connection. But that gets expensive and complicated, and still doesn't allow them to, say, connect to the VPN if they're on the road or at a coffee shop.

So I've been looking into some of the VPN solutions that show up on the Azure marketplace - for instance, VNS3 from Cohesive, or SohaCloud, or pfSense, or whatever. The problem is that these all seem to be focused on the (much more complex) Site-to-Site configuration style - at least, that's what all their documentation seems to be pointing to (for instance, https://cohesive.net/dnld/Cohesive-Networks_VNS3-3.5-Azure.pdf). And all I want is a really simple Point-to-Site configuration.

What's my best (meaning simplest) option here? I'm no network guy, and I start feeling out of my depth (and like I'm headed down a rathole) whenever I start trying to translate the documentation into my particular scenario.

I certainly can't be the only person who's had to figure out how to let OS X clients into an Azure VNet - what's the recommended approach here?

  • Use a Linux VM with OpenVPN to terminate connections from your teleworkers. Better yet, use it as a SSH jumpbox and don't waste your time. If you need RDP access to that Virtual Network you could either spin up a Windows Server VM with a "Terminal Server" role (or whatever kids these days call it now) as a jumpbox, or use OpenVPN on Linux/Windows and RDP from your favorite Mac client. – evilSnobu Sep 14 '16 at 7:16
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They now support the mac natively using IKEv2: https://docs.microsoft.com/en-us/azure/vpn-gateway/point-to-site-vpn-client-configuration-azure-cert#installmac

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You have two workarounds:

  1. Install a Windows Server on the Azure and connect it to the VNET. You may use it as a jumpbox to access the resource on the VNET.

Note: Windows Server only allow 2 users login at same time. If you need to let more than 2 users to connect to the jumpbox, you need to install the RDS services and purchase the CAL.

  1. Install a VPN server on Azure and let your clients connect to the VPN server.

Note: You need to enable the NAT on the VPN server, because the IP addresses of the VPN clients are not registered in Azure and are un-routable. Every VPN client should use the VPN server's internal IP address as the source address when it tries to access the resource in VNET.

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