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I want to automatically connect to wifi and an openvpn connection on startup and resume. I am able to connect to my wifi network automatically on startup. I am also able to select and connect to my VPN manually after logging in.

I selected Automatically connect to this VPN when using this connection for my wifi connection in the Network Connections settings menu (I ran nm-connection-editor to open it).

When I start up, I see the icons on the top right of the taskbar repeatedly toggle the Wifi and Openvpn icons, followed by error messages stating that it failed to establish a connection.

I'm running Ubuntu 18.04 on an HP ENVY x360.

Network device info:

  *-network                 
       description: Wireless interface
       product: Wireless 7265
       vendor: Intel Corporation
       physical id: 0
       bus info: pci@0000:02:00.0
       logical name: wlo1
       version: 61
       serial: 7c:b0:c2:f8:8d:29
       width: 64 bits
       clock: 33MHz
       capabilities: pm msi pciexpress bus_master cap_list ethernet physical wireless
       configuration: broadcast=yes driver=iwlwifi driverversion=4.15.0-46-generic firmware=29.1044073957.0 ip=192.168.1.126 latency=0 link=yes multicast=yes wireless=IEEE 802.11
       resources: irq:156 memory:df100000-df101fff
  *-network
       description: Ethernet interface
       physical id: 2
       logical name: docker0
       serial: 02:42:b1:a1:76:c3
       capabilities: ethernet physical
       configuration: broadcast=yes driver=bridge driverversion=2.3 firmware=N/A ip=172.17.0.1 link=no multicast=yes
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The actual steps depend on how OpenVPN was installed, but if it was installed via the package manager (vs built manually or tarball), there should be a startup script already available. If your (single) config file is in /etc/openvpn/, it should be used to start your OpenVPN daemon (background process).

Notes:

  1. https://openvpn.net/community-resources/how-to/#configuring-openvpn-to-run-automatically-on-system-startup
  2. in the past, I recall the extension had to be .conf on linux, and .opvn on windows? (going off memory, I've used several OS's w/ OpenVPN)
  3. add only a single config file to that directory, because by default (it's configurable), openvpn is going to start all config files located there: see /etc/default/openvpn & /etc/init.d/openvpn
  4. This also assumes the authentication info is supplied in the ovpn config file.

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