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So I've recently installed both Ubuntu 16.04 and Debian 9 (Stretch) as guest machines on VirtualBox on a Windows 10 host. Both are able to connect to the internet just fine when I'm not on VPN (updates, web browsers, etc.). However, when I connect to VPN, which both VM's show that they are connected in the guest, only the Debian VM actually has outside connectivity - Ubuntu encounters "unable to resolve" type errors.

I've checked the network settings within the guests, and both are identical. I've checked the VM network settings, and those are ALSO identical. Does anyone know of a reason this could be happening, and more importantly, what I can do to fix? To me the most confounding part is that one works flawlessly, while the other works not at all. I've even gone so far as to delete the VM and rebuild it from scratch - no luck. Settings are below:

VM Network (Ubuntu & Debian):

  • Attached to NAT
  • Adapter Type: Intel PRO/1000 MT Desktop (82540EM)
  • Promiscuous Mode: Deny
  • MAC Address: 080027DA2981
  • Cable Connected: Checked
  • Port Forwarding: Empty

Guest machine, Ubuntu & Debian:

General

  • Automatically connect to this network when it is available All users may connect to this network

Ethernet

  • Device:
  • Cloned MAC address:
  • MTU: automatic
  • Wake on LAN: Default checked

802.1x Security

  • Everything unchecked/blank

DCB

  • Everything unchecked/blank

IPv4Settings

  • Automatic (DHCP)
  • Everything else blank

IPv6Settings

  • Automatic
  • IPv6 privacy extensions: Enabled (prefer temporary address)
  • Everything else unchecked/blank

Thank you in advance!

Cross posted.

1 Answer 1

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It sounds like it could be a DNS issue. You can confirm this by checking if you can get any pages up via IP address.

If that works, modify /etc/resolve.conf on the Ubuntu box to match that of the Debian box. (If the Debian box uses 127.x.x.x you may need to run additional software on the Ubuntu box or find a Nameserver that can be reached over the VPN)

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