You might find this useful. If you like to live dangerously and accept command line script from strangers on the Internet, you will enjoy this one. It's pretty self-explanatory and harmless, it keeps looping until it manages to get the connect client in a 'connection established' state. If you like you can save this script somewhere as 'connect.cmd' on your Windows 10 machine, and create a shortcut to it that is set to run in minimized state, and then put that shortcut in the Startup folder of Windows. It will then run unobtrusively and keep doing its damnedest to get that connection started no matter what state your system is in. It exits once the connection is up, but if you want it to run forever and forever then replace the last line with "timeout 10 >nul & goto :main" so it always keeps checking.
Behold the fruits of my 2 minutes labor:
@echo off
set serverurl=vpn.yourserver.com
:main
ping -n 1 %serverurl% | find "TTL" >nul
if errorlevel 1 timeout 1 >nul & goto :main
"C:\Program Files (x86)\OpenVPN Technologies\OpenVPN Client\core\ovpncli.exe" Status | find "established" >nul
if errorlevel 1 "C:\Program Files (x86)\OpenVPN Technologies\OpenVPN Client\core\ovpncli.exe" Connect >nul
"C:\Program Files (x86)\OpenVPN Technologies\OpenVPN Client\core\ovpncli.exe" Status | find "established" >nul
if errorlevel 1 timeout 10 >nul & goto :main