Given: vm - a WinXPsp3 virtual machine hosted by a Win7sp1 physical machine alice is the user on vm srv - a Win2008R2sp1 server bob is the user on srv quake - a linux server mark is the user on quake Both vm and srv have the same new installation of cygwin (1.7.9) and openssh. Firewall service is disabled on vm (and its host) and on srv All the machines can be pinged from all the machines. ssh mark@quake works OK from both vm and srv. ssh bob@srv works OK from both quake and vm. ssh alice@vm works on the vm itself only, but it fails on the other two machines: alice@vm ~ $ ssh alice@vm alice@vm's password: Last login: Tue Oct 25 23:42:09 2011 from vm.shunra.net [mark@Quake ~]$ ssh -vvv alice@vm OpenSSH_4.3p2, OpenSSL 0.9.8e-fips-rhel5 01 Jul 2008 debug1: Reading configuration data /etc/ssh/ssh_config debug1: Applying options for * debug2: ssh_connect: needpriv 0 debug1: Connecting to vm [172.30.2.60] port 22. debug1: connect to address 172.30.2.60 port 22: Connection timed out ssh: connect to host vm port 22: Connection timed out bob@Srv ~ $ ssh -vvv alice@vm OpenSSH_5.9p1, OpenSSL 0.9.8r 8 Feb 2011 debug1: Reading configuration data /etc/ssh_config debug2: ssh_connect: needpriv 0 debug1: Connecting to vm [172.30.2.60] port 22. debug1: connect to address 172.30.2.60 port 22: Connection timed out ssh: connect to host vm port 22: Connection timed out I used ssh-host-config both on vm and srv to configure the ssh to run as a windows service. Besides that I did nothing else. Can anyone help me troubleshoot this issue? Thank you very much. EDIT The virtual machine software is VMWare Workstation 7.1.4. I think the problem is in its settings, but I have no idea where exactly. The Network Adapter is set to Bridged. EDIT2 All the machines are located in the company lab, I think all of them are on the same segment, but I may be wrong. Below is the ipconfig /all output for each machine (skipping the linux server). I have deleted the Tunnel adapters to keep the output minimal. If anyone thinks they matter, do tell so and I will post them as well. In addition ping output is given to show that DNS is correct. Something else, may be relevant, may be not. Doing psexec to srv works OK, whereas to vm failes with Access Denied. srv: C:\Windows\system32>ipconfig /all Windows IP Configuration Host Name . . . . . . . . . . . . : srv Primary Dns Suffix . . . . . . . : shunra.net Node Type . . . . . . . . . . . . : Hybrid IP Routing Enabled. . . . . . . . : No WINS Proxy Enabled. . . . . . . . : No DNS Suffix Search List. . . . . . : shunra.net Ethernet adapter Local Area Connection: Connection-specific DNS Suffix . : Description . . . . . . . . . . . : Broadcom BCM5709C NetXtreme II GigE (NDIS VBD Client) Physical Address. . . . . . . . . : E4-1F-13-6D-F3-00 DHCP Enabled. . . . . . . . . . . : No Autoconfiguration Enabled . . . . : Yes IPv4 Address. . . . . . . . . . . : 172.30.6.9(Preferred) Subnet Mask . . . . . . . . . . . : 255.255.248.0 Default Gateway . . . . . . . . . : 172.30.0.254 DNS Servers . . . . . . . . . . . : 172.30.1.1 172.30.1.2 NetBIOS over Tcpip. . . . . . . . : Enabled C:\Windows\system32>ping vm Pinging vm.shunra.net [172.30.2.60] with 32 bytes of data: Reply from 172.30.2.60: bytes=32 time=1ms TTL=128 Reply from 172.30.2.60: bytes=32 time=4ms TTL=128 Reply from 172.30.2.60: bytes=32 time<1ms TTL=128 Reply from 172.30.2.60: bytes=32 time<1ms TTL=128 Ping statistics for 172.30.2.60: Packets: Sent = 4, Received = 4, Lost = 0 (0% loss), Approximate round trip times in milli-seconds: Minimum = 0ms, Maximum = 4ms, Average = 1ms C:\Windows\system32> vm: C:\>ipconfig /all Windows IP Configuration Host Name . . . . . . . . . . . . : vm Primary Dns Suffix . . . . . . . : shunra.net Node Type . . . . . . . . . . . . : Hybrid IP Routing Enabled. . . . . . . . : No WINS Proxy Enabled. . . . . . . . : No DNS Suffix Search List. . . . . . : shunra.net shunranet Ethernet adapter Local Area Connection: Connection-specific DNS Suffix . : shunranet Description . . . . . . . . . . . : VMware Accelerated AMD PCNet Adapter Physical Address. . . . . . . . . : 00-0C-29-8F-A0-0B Dhcp Enabled. . . . . . . . . . . : Yes Autoconfiguration Enabled . . . . : Yes IP Address. . . . . . . . . . . . : 172.30.2.60 Subnet Mask . . . . . . . . . . . : 255.255.248.0 Default Gateway . . . . . . . . . : 172.30.0.254 DHCP Server . . . . . . . . . . . : 172.30.1.1 DNS Servers . . . . . . . . . . . : 172.30.1.1 172.30.1.2 Lease Obtained. . . . . . . . . . : Tuesday, October 25, 2011 18:16:34 Lease Expires . . . . . . . . . . : Wednesday, November 02, 2011 18:16:34 C:\>ping srv Pinging srv.shunra.net [172.30.6.9] with 32 bytes of data: Reply from 172.30.6.9: bytes=32 time=1ms TTL=128 Reply from 172.30.6.9: bytes=32 time<1ms TTL=128 Reply from 172.30.6.9: bytes=32 time<1ms TTL=128 Reply from 172.30.6.9: bytes=32 time<1ms TTL=128 Ping statistics for 172.30.6.9: Packets: Sent = 4, Received = 4, Lost = 0 (0% loss), Approximate round trip times in milli-seconds: Minimum = 0ms, Maximum = 1ms, Average = 0ms C:\> vm-host (the host machine of the vm): C:\>ipconfig /all Windows IP Configuration Host Name . . . . . . . . . . . . : vm-host Primary Dns Suffix . . . . . . . : shunra.net Node Type . . . . . . . . . . . . : Hybrid IP Routing Enabled. . . . . . . . : No WINS Proxy Enabled. . . . . . . . : No DNS Suffix Search List. . . . . . : shunra.net Ethernet adapter Local Area Connection: Connection-specific DNS Suffix . : Description . . . . . . . . . . . : Realtek RTL8168D/8111D Family PCI-E Gigabit Ethernet NIC (NDIS 6.20) Physical Address. . . . . . . . . : 6C-F0-49-E7-E9-30 DHCP Enabled. . . . . . . . . . . : No Autoconfiguration Enabled . . . . : Yes Link-local IPv6 Address . . . . . : fe80::f59d:7f6e:1510:6f%10(Preferred) IPv4 Address. . . . . . . . . . . : 172.30.6.7(Preferred) Subnet Mask . . . . . . . . . . . : 255.255.248.0 Default Gateway . . . . . . . . . : 172.30.0.254 DHCPv6 IAID . . . . . . . . . . . : 242020425 DHCPv6 Client DUID. . . . . . . . : 00-01-00-01-13-CC-39-80-6C-F0-49-E7-E9-30 DNS Servers . . . . . . . . . . . : 172.30.1.1 194.90.1.5 NetBIOS over Tcpip. . . . . . . . : Enabled Ethernet adapter VMware Network Adapter VMnet1: Connection-specific DNS Suffix . : Description . . . . . . . . . . . : VMware Virtual Ethernet Adapter for VMnet1 Physical Address. . . . . . . . . : 00-50-56-C0-00-01 DHCP Enabled. . . . . . . . . . . : No Autoconfiguration Enabled . . . . : Yes Link-local IPv6 Address . . . . . : fe80::cd92:38c0:9a6d:c008%16(Preferred) Autoconfiguration IPv4 Address. . : 169.254.192.8(Preferred) Subnet Mask . . . . . . . . . . . : 255.255.0.0 Default Gateway . . . . . . . . . : DHCPv6 IAID . . . . . . . . . . . : 352342102 DHCPv6 Client DUID. . . . . . . . : 00-01-00-01-13-CC-39-80-6C-F0-49-E7-E9-30 DNS Servers . . . . . . . . . . . : fec0:0:0:ffff::1%1 fec0:0:0:ffff::2%1 fec0:0:0:ffff::3%1 NetBIOS over Tcpip. . . . . . . . : Enabled Ethernet adapter VMware Network Adapter VMnet8: Connection-specific DNS Suffix . : Description . . . . . . . . . . . : VMware Virtual Ethernet Adapter for VMnet8 Physical Address. . . . . . . . . : 00-50-56-C0-00-08 DHCP Enabled. . . . . . . . . . . : No Autoconfiguration Enabled . . . . : Yes Link-local IPv6 Address . . . . . : fe80::edb9:b78c:a504:593b%17(Preferred) IPv4 Address. . . . . . . . . . . : 192.168.5.1(Preferred) Subnet Mask . . . . . . . . . . . : 255.255.255.0 Default Gateway . . . . . . . . . : DHCPv6 IAID . . . . . . . . . . . : 369119318 DHCPv6 Client DUID. . . . . . . . : 00-01-00-01-13-CC-39-80-6C-F0-49-E7-E9-30 DNS Servers . . . . . . . . . . . : fec0:0:0:ffff::1%1 fec0:0:0:ffff::2%1 fec0:0:0:ffff::3%1 NetBIOS over Tcpip. . . . . . . . : Enabled C:\>ping srv Pinging srv.shunra.net [172.30.6.9] with 32 bytes of data: Reply from 172.30.6.9: bytes=32 time<1ms TTL=128 Reply from 172.30.6.9: bytes=32 time<1ms TTL=128 Reply from 172.30.6.9: bytes=32 time<1ms TTL=128 Reply from 172.30.6.9: bytes=32 time<1ms TTL=128 Ping statistics for 172.30.6.9: Packets: Sent = 4, Received = 4, Lost = 0 (0% loss), Approximate round trip times in milli-seconds: Minimum = 0ms, Maximum = 0ms, Average = 0ms C:\>ping vm Pinging vm.shunra.net [172.30.2.60] with 32 bytes of data: Reply from 172.30.2.60: bytes=32 time<1ms TTL=128 Reply from 172.30.2.60: bytes=32 time<1ms TTL=128 Reply from 172.30.2.60: bytes=32 time<1ms TTL=128 Reply from 172.30.2.60: bytes=32 time<1ms TTL=128 Ping statistics for 172.30.2.60: Packets: Sent = 4, Received = 4, Lost = 0 (0% loss), Approximate round trip times in milli-seconds: Minimum = 0ms, Maximum = 0ms, Average = 0ms C:\> EDIT3 I have just checked - the vm-host is able to ssh to the vm machine! I still do not know how to leverage this discovery to solve the problem.