Hi Jordan, I'd recommend the following. The Plesk hoster or VPS owner can prepare the environment by himself. See: http://devblog.plesk.com/2014/09/plesk-and-ruby-on-rails/ http://devblog.plesk.com/2014/10/plesk-and-django/ (full disclosure, I work for Parallels & had our dev team take a look at this question.)