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I am trying to rdp from my local mac to an Azure instance through a (IKEv2) vpn connection. I am never prompted for a password, and it looks like the connection just times out. The error code I get is 0x204.

I have tried using both Microsoft Remote Desktop 8 and 10 for mac.

The connection is active and reports that it is connected.

From the mac, I can connect to another VM (in the same azure account) which is not running behind a vpn.

From Parallels Desktop (with networking set to Shared mode and the vpn connection active on the mac), I can successfully connect using the windows rdp client.

So it seems the Microsoft RDP-client for mac is not using the vpn connection.

Is there a way to make it do so?

Is there another solution, that will allow me to rdp to an Azure VM from my mac (without going through Parallels)?

Note: This is not the same question as this, since that is not about going through an azure vnet gateway.

AdamAL
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  • i think you need to add a route to connect to that subnet through vnet gateway, windows does that by default, mac obviously cant because its crap ;) – 4c74356b41 Mar 07 '19 at 14:21
  • Could you elaborate on how to "add a route to connect to that subnet"? – AdamAL Mar 07 '19 at 14:26
  • not a Linux person exactly, it's easily Google able. it's route add in windows – 4c74356b41 Mar 07 '19 at 14:32
  • I, on the other hand, am not strong in networking. From your cues, and googling, I figure your suggestion has to do with static routing, though I am not even exactly sure what that would mean in this context. Could you elaborate on what you think the basic failure mode is, and what conceptually needs to happen to make it work? – AdamAL Mar 07 '19 at 15:19
  • looking at official doc, this might not be needed, did you follow this: https://learn.microsoft.com/en-us/azure/vpn-gateway/point-to-site-vpn-client-configuration-azure-cert#installmac ? – 4c74356b41 Mar 07 '19 at 15:22
  • Yes, that is the guide I followed. – AdamAL Mar 07 '19 at 15:25
  • i think that xml file should instruct mac os to forward connections, does ping or trace work? something native to macos? – 4c74356b41 Mar 07 '19 at 15:27
  • Unless I am missing something, the only use of the xml in the guide is to get the value from the `VpnServer` tag. I can `traceroute` the adresses of both the working and non-working rdp connections. Ping times out for both. I get an error (hostname too long) when traceroute'ing the VpnServer value. – AdamAL Mar 07 '19 at 15:45

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I needed to add hosts file entries for each azure site I needed to access.

For example for accessing my-vm-name.someregion.cloudapp.azure.com, I needed to add a hosts file entry for it's private IP within the subnet. E.g. 10.2.0.100.

The reason everything worked in Windows under Parallels, is that the relevant entries had already been added to the hosts file previously.

AdamAL
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