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We have a Windows 7 PC with 3 network adapters (2 physical and 1 virtual):

Ethernet adapter Local Area Connection:

Connection-specific DNS Suffix  . :
   IPv4 Address. . . . . . . . . . . : 192.168.75.20
   Subnet Mask . . . . . . . . . . . : 255.255.255.0
   Default Gateway . . . . . . . . . : 192.168.75.1


Unknown adapter Local Area Connection 3:


Connection-specific DNS Suffix  . :
   IPv4 Address. . . . . . . . . . . : 10.8.0.3
   Subnet Mask . . . . . . . . . . . : 255.255.0.0
   Default Gateway . . . . . . . . . :


Ethernet adapter Local Area Connection 2:


Connection-specific DNS Suffix  . :
   IPv4 Address. . . . . . . . . . . : 192.168.1.253
   Subnet Mask . . . . . . . . . . . : 255.255.255.0
   IPv4 Address. . . . . . . . . . . : 192.168.150.2
   Subnet Mask . . . . . . . . . . . : 255.255.255.0
   IPv4 Address. . . . . . . . . . . : 192.168.255.126
   Subnet Mask . . . . . . . . . . . : 255.255.252.0
   Default Gateway . . . . . . . . . :

When I disable the Local Area Connection 3 virtual adapter, I am able to Remote Desktop to another machine on the corporate network with IP address 172.27.117.78. But if the Local Area Connection 3 adapter is enabled, then the Remote Desktop fails to connect to 172.27.117.78. Apparently Windows tries to connect to 172.27.117.78 using Local Area Connection 3 which cannot access that machine.

So I tried to have Windows give priority to the Local Area Connection adapter, using the answers here:

  • I set Local Area Connection properties > TCP/IPv4 properties > Advanced > Interface metric = 1
  • I set Local Area Connection 2 properties > TCP/IPv4 properties > Advanced > Interface metric = 2
  • I set Local Area Connection 3 properties > TCP/IPv4 properties > Advanced > Interface metric = 3
  • I went to Control Panel > Network and Internet > Network Connections > Advanced > Advanced Settings > Adapters and Bindings, and moved Local Area Connection to the top of the list, Local Area Connection 2 below that, and Local Area Connection 3 below that.

After doing all that, the Remote Desktop still fails to connect to 172.27.117.78 if the Local Area Connection 3 adapter is enabled.

Also, I tried disabling Local Area Connection 2 to remove it from the equation. Same problem, when Local Area Connection 3 is disabled, the Remote Desktop connection works, but when Local Area Connection 3 is enabled, the Remote Desktop connection fails.

Edit: Here is the output of route print (the "82579LM" interface is Local Area Connection and the "TAP-Windows Adapter V9" interface is Local Area Connection3):

C:\WINDOWS\system32>route print
===========================================================================
Interface List
 11...xx xx xx xx xx xx ......Intel(R) 82579LM Gigabit Network Connection
 13...xx xx xx xx xx xx ......Intel(R) Gigabit CT Desktop Adapter
 16...xx xx xx xx xx xx ......TAP-Windows Adapter V9
  1...........................Software Loopback Interface 1
 12...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter
 14...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter #2
 15...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter #3
===========================================================================

IPv4 Route Table


Active Routes:
Network Destination        Netmask          Gateway       Interface  Metric
          0.0.0.0          0.0.0.0     192.168.75.1    192.168.75.20    257
          0.0.0.0        128.0.0.0         10.8.0.1         10.8.0.3      3
         10.8.0.0      255.255.0.0         On-link          10.8.0.3    259
         10.8.0.3  255.255.255.255         On-link          10.8.0.3    259
     10.8.255.255  255.255.255.255         On-link          10.8.0.3    259
         54.x.x.x  255.255.255.255     192.168.75.1    192.168.75.20      1
        127.0.0.0        255.0.0.0         On-link         127.0.0.1    306
        127.0.0.1  255.255.255.255         On-link         127.0.0.1    306
  127.255.255.255  255.255.255.255         On-link         127.0.0.1    306
        128.0.0.0        128.0.0.0         10.8.0.1         10.8.0.3      3
      192.168.1.0    255.255.255.0         On-link     192.168.1.253    258
    192.168.1.253  255.255.255.255         On-link     192.168.1.253    258
    192.168.1.255  255.255.255.255         On-link     192.168.1.253    258
     192.168.75.0    255.255.255.0         On-link     192.168.75.20    257
    192.168.75.20  255.255.255.255         On-link     192.168.75.20    257
   192.168.75.255  255.255.255.255         On-link     192.168.75.20    257
    192.168.150.0    255.255.255.0         On-link     192.168.1.253    258
    192.168.150.2  255.255.255.255         On-link     192.168.1.253    258
  192.168.150.255  255.255.255.255         On-link     192.168.1.253    258
    192.168.252.0    255.255.252.0         On-link     192.168.1.253    258
  192.168.255.126  255.255.255.255         On-link     192.168.1.253    258
  192.168.255.255  255.255.255.255         On-link     192.168.1.253    258
        224.0.0.0        240.0.0.0         On-link         127.0.0.1    306
        224.0.0.0        240.0.0.0         On-link     192.168.75.20    257
        224.0.0.0        240.0.0.0         On-link     192.168.1.253    258
        224.0.0.0        240.0.0.0         On-link          10.8.0.3    259
  255.255.255.255  255.255.255.255         On-link         127.0.0.1    306
  255.255.255.255  255.255.255.255         On-link     192.168.75.20    257
  255.255.255.255  255.255.255.255         On-link     192.168.1.253    258
  255.255.255.255  255.255.255.255         On-link          10.8.0.3    259
===========================================================================
Persistent Routes:
  Network Address          Netmask  Gateway Address  Metric
          0.0.0.0          0.0.0.0     192.168.75.1  Default
===========================================================================


IPv6 Route Table


Active Routes:
 If Metric Network Destination      Gateway
  1    306 ::1/128                  On-link
  1    306 ff00::/8                 On-link
===========================================================================
Persistent Routes:
  None
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