I didn't think Windows had support for VPN at all. Last time I checked I
thought you needed some third party VPN client from e.g. Cisco.

You could try another client in Ubuntu as well, like kvpn. It could have
more options for reconnection.

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Packages, which is subscribed to network-manager in Ubuntu.
https://bugs.launchpad.net/bugs/280571

Title:
  NetworkManager does not auto-connect to VPNs marked "Connect
  Automatically"

Status in NetworkManager:
  Confirmed
Status in “network-manager” package in Ubuntu:
  Triaged
Status in Debian GNU/Linux:
  New

Bug description:
  VPN connections marked "Connect Automatically" are not activated when
  a wired or wireless network becomes available.

To manage notifications about this bug go to:
https://bugs.launchpad.net/network-manager/+bug/280571/+subscriptions

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