Before Skyline, DigitPaint developed a content management system in PHP which went by the name of Xandra. This flexible cms was made redundant when DigitPaint dropped PHP development in favor of Ruby on Rails in 2005.
Thus began the development of Skyline. Back then, Skyline was developed as a proprietary cms mainly focussed on fast implementations of content managed websites. In 2007 Skyline 2 was released with some major improvements to the core and usability.
Since 2009 DigitPaint has been working on Skyline 3 which will be released as open source. Skyline 3 has a renewed user interface focussing mainly on the users of the cms and the Skyline core has been improved and extended with many new functionalities.