Circling back to GPP. Thanks to @FiyaFly , who was able to help me out with the syntax for the fields. Do not use quotes in the target or start in paths. Target Path: C:\Program Files (x86)\Google\Chrome\Application\chrome.exe Arguments: --incognito --proxy-server=squid1.domain.com:3128 --user-data-dir="%LOCALAPPDATA%\Google\Squid1\User Data" Start in: C:\Program Files (x86)\Google\Chrome\Application\ I also used the create option and desktop (standard, not all users desktop).