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[birdmantd]

Mac is unable to connect via RDP to a virtual server using a L2TP VPN.

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Tags: Mac, Networking, Windows

There are 5 servers. 2 physical servers (OS Windows 10 Pro) containing 3 virtual servers (OS Windows Server 2003). There is also an L2TP VPN connection by a MikroTik.

VPN Type: L2TP/IPsec with pre-shared key

# Physical Server 1 (IP: 192.168.1.14) (OS Windows 10 Pro) contains
1. Network server (IP: 192.168.1.11) – (OS Windows Server 2003) VMware Virtual Server
2. ERP server (IP: 192.168.1.12) – (OS Windows Server 2003) VMware Virtual Server

# Physical Server 2 (IP: 192.168.1.15) (OS Windows 10 Pro) contains
1. SQL server (IP: 192.168.1.13) – (OS Windows Server 2003) VMware Virtual Server

Now whenever I connect the VPN and try to connect with the server with a windows PC all works fine. But there is a Mac user. The problem is, after connecting with the VPN the MacBook Pro(macOS Monterey 12) user can connect with the physical servers (192.168.1.14 and 192.168.1.15) but the user can’t connect with the virtual servers (192.168.1.11, 192.168.1.12 and 192.168.1.13).

How can I solve this problem?

• This topic was modified 1 year, 5 months ago by birdmantd.

Topic

Sounds like a mess.

In reply to Mac is unable to connect via RDP to a virtual server using a L2TP VPN.

No one I know would, in a business do this. It’s too far out of what we would actually setup in a business.

Also, Server 2003 is end of life. No one would or should run this today (unpatched vulnerabilities.)

But as it works with the Windows PC, it’s a Mac issue. Maybe Mac is being more secure.

My advice is to forget the virtual servers and install the Servers on their own iron.

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