Windows Server 2016 Remote Desktop problem on secondary IP address

Question

Windows Server 2016 Remote Desktop problem on secondary IP address

Steve Palm 1

Trying to set up a Windows Server 2016 install so that we can access it over a ZeroTier network instead of the current VPN solution. Connecting to it in Desktop/PC mode is no problem at all, but when I try to add a Workspace to use published apps I can authenticate and pull down the list of applications, but when it tries to connect to and configure the gateway for the connection it fails on the Mac with error 0x300005f.

The connection dialog shows that it is trying to connect to the IP address set up for the VPN, it is as though the gateway (sorry, I don't have all the right terms) is not pulling the right IP address based on where we are connecting from.

I had followed a post here: https://social.technet.microsoft.com/Forums/en-US/757ab679-ec7e-448a-a3cc-89da9d9fbaad/rdweb-connecting-to-wrong-server?forum=winserverTS

I set up a Local Computer Group with all the IP addresses involved and set the policy for the gateway in the resource authorization and connection authorization policies.

What piece am I missing that would allow the server to accept connections on more than one IP address for Workspaces/RDWeb apps? It is maddening that it works 99% except for actually launching the application.

It would be great if somehow we could just add the workspace with the IP address (which I am using in the URL), but it seems to have to route through the gateway which is configuring things for the wrong IP address.

Eleven Yu (Shanghai Wicresoft Co,.Ltd.) 10,801 Reputation points Microsoft External Staff

2020-12-03T08:10:46.647+00:00
Hi,

Sorry, could you please provide a more clear clarification so that we can better understand your problem?

Please describe your RDS deployment? How you installed the RDS session host, RDCB, RDWeb, RD Gatway role?

How client PC connect to the remote desktop and access remote apps? RDP file? mstsc? Microsoft Remote Desktop App?

What is exactly the problem you are facing? The error occurs on client Mac PC? What action you have done when the issue occurred?

Thanks,
Eleven
Steve Palm 1 Reputation point

2020-12-03T20:54:16.497+00:00

It is a single azure hosted windows server instance.

It has multiple IP addresses, one on the NIC and two zerotier networks that show up as separate network interfaces, all of them are Domain networks.

It was set up by a consultant who we parted ways with due to the fact they couldn't get many things working, I am not familiar with TerminalServices/RemoteApps/etc, trying to learn as I go.

The public IP is blocked by firewall, I had set up a Linux azure VM running a VPN on the same virtual network as the windows server host, and they were using that to connect to the system using the NIC IP address.

All clients are using Mac Microsoft Remote Desktop app.

The problem is that while I can start a remote desktop session as PC/Desktop, trying to access workspace/published apps gives an error because it is trying to connect to the NIC address instead of the zerotier network interface the connection is coming in on. I don't know why the two types of connections behave differently.

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Eleven Yu (Shanghai Wicresoft Co,.Ltd.) 10,801 Reputation points Microsoft External Staff

2020-12-03T08:10:46.647+00:00

Hi,

Sorry, could you please provide a more clear clarification so that we can better understand your problem?

Please describe your RDS deployment? How you installed the RDS session host, RDCB, RDWeb, RD Gatway role?

How client PC connect to the remote desktop and access remote apps? RDP file? mstsc? Microsoft Remote Desktop App?

What is exactly the problem you are facing? The error occurs on client Mac PC? What action you have done when the issue occurred?

Thanks,
Eleven
Steve Palm 1 Reputation point

2020-12-03T20:54:16.497+00:00

It is a single azure hosted windows server instance.

It has multiple IP addresses, one on the NIC and two zerotier networks that show up as separate network interfaces, all of them are Domain networks.

It was set up by a consultant who we parted ways with due to the fact they couldn't get many things working, I am not familiar with TerminalServices/RemoteApps/etc, trying to learn as I go.

The public IP is blocked by firewall, I had set up a Linux azure VM running a VPN on the same virtual network as the windows server host, and they were using that to connect to the system using the NIC IP address.

All clients are using Mac Microsoft Remote Desktop app.

The problem is that while I can start a remote desktop session as PC/Desktop, trying to access workspace/published apps gives an error because it is trying to connect to the NIC address instead of the zerotier network interface the connection is coming in on. I don't know why the two types of connections behave differently.

Answer 1

Eleven Yu (Shanghai Wicresoft Co,.Ltd.) 10,801 Microsoft External Staff

Hi,

Thanks for your detailed explanation. From your description, the prolems should be more related to azure networking.

So, we suggest that you can post your question to azure network team.
https://learn.microsoft.com/en-us/answers/questions/topics/single/25516.html

And maybe your problem will need to capture some dumps or traces to further analysis, which I suggest to contact Microsoft Customer Support and Services where more in-depth investigation can be done so that you would get a more satisfying explanation and solution to this issue.

You may find phone number for your region accordingly from the link below:
Global Customer Service phone numbers
https://support.microsoft.com/en-us/help/4051701/global-customer-service-phone-numbers

Thanks,
Eleven

Steve Palm 1 Reputation point

2020-12-04T09:00:50.237+00:00

It has nothing to do with Azure networking, as I can connect to it using any of the IP addresses, so all networking is functioning as it should. The problem is that however the published apps work, they insist on using the wrong IP which seems squarely in the gateway/broker/whatever configuration.

And again, in case you missed it, I can open a desktop control session fine from any address, I just can not used the published apps, whatever they are called.

How does one set up a server with multiple NICs on different nets and allow full remote app functionality? Essentially that is what this is, but it is trying to make everyone connecting on NIC2 connect to the IP of NIC1 which they can not reach.

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Windows Server 2016 Remote Desktop problem on secondary IP address

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