I've had the same problem for about a year, and now, I think, I've finally found the way to fix it (at least somehow).
Looks like in my case it was the same as in https://bugs.launchpad.net/ubuntu/+source/network- manager/+bug/991666/comments/16 (duplicate routes entries). So what I've done. - run `sudo route -n` before connecting to VPN and after - found entries that were pushed from the VPN server - found duplicate entry - manually added all but duplicate pushed entries to routes (Network connections -> your VPN connection -> IPv4 settings -> Routes -> Add ...) and checked "Ignore automatically obtained routes" checkbox. - restarted VPN connection Since that all works just fine. Thanks to @botevmg! -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/991666 Title: VPN Connects Successfully & Then Shortly Thereafter Fails To manage notifications about this bug go to: https://bugs.launchpad.net/network-manager-pptp/+bug/991666/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs