How to Upgrade Debian 7 Wheezy to Debian 8 Jessie. Worked perfectly on a VPS I have. I did get bit by a couple of things so be sure to check Issues to be aware of for jessie. I specifically got hit with: Apache Upgrading to 2.4 from 2.2. This went smooth enough I'm going to migrate my CentOS servers over to Debian (there's no way to go from CentOS 6 to 7, you have to start from scratch and rebuild... Screw that noise.)