If you have received following message from dreamhost on VPS upgrade and your Ruby apps are broken then here are few tips that might save your day. "We will be upgrading your Virtual Private Server from version 14.04 (also known as trusty) to Debian 9.12 (aka Stretch!) ". Yes as they mentioned in their email that there are some environment changes that effect your system if you are using Ruby, Python, PHP, or run a site that relies heavily on specific server packages. Lets start with Ubuntu To Debian Upgrade Issues on VPS of Dreamhost. This post will help you only if you have already installed redmine on dreamhost VPS and your server is now upgraded to Debain Stretch. SVN Write