So I really didn't want to remember an insane password to connect to my OpenVPN, and I don't have the luxury of controller the certificate signing, meaning that I can't create a signed key certificate file to use.

Disclaimer: I realize the solution described in this post is not ideal, but IMO it's better than keeping the password in a plain-text file on the desktop (like my boss does).

AutoHotkey can be found here.

AHK Script:

 #Persistent
 SetTimer, EnterAuth, 250
 return
 
 EnterAuth:
 Process, wait, openvpn-gui.exe, 2
 If %ErrorLevel% = 0
 {
 Run, C:\Program Files (x86)\OpenVPN\config\shortcut.lnk
 Sleep, 2000
 }
 IfWinExist OpenVPN - User Authentication
 {
 ControlSetText, Edit1, {USERNAME}, OpenVPN - User Authentication ahk_class #32770
 ControlSetText, Edit2, {PASSWORD}, OpenVPN - User Authentication ahk_class #32770
 ControlSend, Edit1, {Enter}, OpenVPN - User Authentication ahk_class #32770
 ExitApp
 }
 return

Where {USERNAME}/{PASSWORD} get replaced by your OpenVPN username and password, and the shortcut.lnk is a shortcut to openvpn with the connect command, i.e.:

 "C:\Program Files (x86)\OpenVPN\bin\openvpn-gui-1.0.3.exe" --connect my-openvpn-config.ovpn

I then compiled the executable and added a scheduled task to run after user logon to run the executable and trigger OpenVPN to launch. It works great.