So my further question is: is this how VBox bridged networking supposed to be setup? Any rationale behind this? I'd appreciate if someone could provide some explaination on VBox bridged networking setup on Windows host and I'll accept it as an answer. While the same checkbox of the physical NIC (that is bridged to) is checked. I've also noticed that in the properties windows (see screenshot below) of the "VirtualBox Host-Only Network", the second checkbox, "VirtualBox Bridged Networking Driver" is unchecked. And now I can SSH into 192.168.1.4 with no problem, even without touching hosts.allow and ny. Once I change the "VirtualBox Host-Only Network" to automatically obtain an IP address, it's getting a different IP address of 169.254.249.70(Tentative). When system boots, your VM should now be running. sudo systemctl restart vboxautostart-service Testing the Virtual Machine autostart To test that your virtual machine can actually autostart on system boot, reboot you system and check. When using a bridged connection you are bridging the virtual network of the guest (VM) to the physical network device of the host (Windows 10). Right click and select 'Bridge Connections', it's going to create a network bridge in Windows. Then in the Windows 7 host, in the Network and Sharing Center, there is a new connection named "VirtualBox Host-Only Network" after the bridge is setup, that connection is again given the same static IP of 192.168.1.4. To effect the settings, you need to restart the vboxautostart-service. go to Network connections on Windows and highlight both the real adapter and the new virtual ethernet adapter that you just created. I give the Ubuntu guest a static IP of 192.168.1.4 (assigned to eth0). It turned out to be a wrong VirtualBox Bridged Network setup. When I the following command, I can see that sshd is listening on port 22: lsof -i tcp:22 However, when I try to PuTTY into the ubuntu machine, I always get "connection refused". The guest has bridged network setup, I can ping 192.168.1.4 from any machine in the LAN, the ubuntu guest can also access the LAN. The ubuntu guest is given a static IP of 192.168.1.4, which also has openssh installed. I have virtualbox running on a Windows 2008 server, with a guest running ubuntu 10.04.
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