Just to make sure that we are on the same page here, that the Windows 2008 server is NOT a virtual machine and the target that you are trying to connect is not being used by any other initiator.

If you can ping from the Windows 2008 server to the DSS being the same subnet and no VLAN and maybe try to directly connect the Windows 2008 directly to the DSS server to rule out any network issues from the Windows to the DSS side.

Also check the Windows event logs as well to see if there is any errors coming up.