Upgrading websites built using Telerik’s Sitefinity CMS is now a whole lot easier! Keeping your website is always important, not only to get the latest security updates; but also the latest features.
Sitefinity now has a project manager (windows app) that allows for incremental upgrades: http://www.sitefinity.com/documentation/documentationarticles/installation-and-administration-guide/install-sitefinity/downloading-and-installing-sitefinity
A quick hint I could give you here is to not download the full Sitefinity msi installers but instead just use the exe project manager for the particular versions. I have broken down the process into 3 or 4 upgrade steps simply because we go two versions back in our automated tests for the upgrade, so it’s best to go either in the path of 4.2 ->4.3 Hotfix 1->4.4->5.0 SP1 Hotfix 1->5.1 SP2 or potentially you can skip 4.3 and go directly to 4.4.
Since 5.0 and 5.1 introduce some changes to the web config and the project, it’s best to handle those without skipping.
For the full documentation see: http://www.sitefinity.com/documentation/documentationarticles/installation-and-administration-guide/upgrade