Thank you for your bug report. What VPN type/plugin are you using?
Could you add your 'journalctl -b 0' log after getting the issue?

** No longer affects: network-manager

** Changed in: network-manager (Ubuntu)
   Importance: Undecided => Low

** Changed in: network-manager (Ubuntu)
       Status: New => Incomplete

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Touch seeded packages, which is subscribed to network-manager in Ubuntu.
https://bugs.launchpad.net/bugs/1851322

Title:
  VPN auto-connect is not working

Status in network-manager package in Ubuntu:
  Incomplete

Bug description:
  Hi,

  This is a duplicate of bug:
  https://bugs.launchpad.net/network-manager/+bug/1718931

  It is marked as fixed, but the feature is still broken for me.

  I configured my Wifi connection to automatically connect to a VPN, but it 
only works if I manually
  connect to the Wifi via NetworkManager.

  ProblemType: Bug
  DistroRelease: Ubuntu 19.10
  Package: network-manager 1.20.4-2ubuntu2
  ProcVersionSignature: Ubuntu 5.3.0-19.20-generic 5.3.1
  Uname: Linux 5.3.0-19-generic x86_64
  NonfreeKernelModules: nvidia_modeset nvidia
  ApportVersion: 2.20.11-0ubuntu8.1
  Architecture: amd64
  CurrentDesktop: ubuntu:GNOME
  Date: Tue Nov  5 04:07:00 2019
  IfupdownConfig:
   # interfaces(5) file used by ifup(8) and ifdown(8)
   auto lo
   iface lo inet loopback
  InstallationDate: Installed on 2019-09-26 (39 days ago)
  InstallationMedia: Ubuntu 19.04 "Disco Dingo" - Release amd64 (20190416)
  SourcePackage: network-manager
  UpgradeStatus: No upgrade log present (probably fresh install)
  nmcli-nm:
   RUNNING  VERSION  STATE      STARTUP  CONNECTIVITY  NETWORKING  WIFI-HW  
WIFI     WWAN-HW  WWAN    
   running  1.20.4   connected  started  full          enabled     enabled  
enabled  enabled  enabled

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