The VLT Data Flow System (DFS) has been developed to maximize the scientific output from the operation of the ESO observatory facilities. From its original conception in the mid 90s till the system now in production at Paranal, at La Silla, at the ESO HQ and externally at home institutes of astronomers, extensive efforts, iteration and retrofitting have been invested in the DFS to maintain a good level of performance and to keep it up to date. In the end what has been obtained is a robust, efficient and reliable 'science support engine', without which it would be difficult, if not impossible, to operate the VLT in a manner as efficient and with such great success as is the case today. Of course, in the end the symbiosis between the VLT Control System (VCS) and the DFS plus the hard work of dedicated development and operational staff, is what has made the success of the VLT possible. Although the basic framework of DFS can be considered as 'completed' and that DFS has been in operation for approximately 3 years by now, the implementation of improvements and enhancements is an ongoing process mostly due to the appearance of new requirements. This article describes the origin of such new requirements towards DFS and discusses the challenges that have been faced adapting the DFS to an ever-changing operational environment. Examples of recent, new concepts designed and implemented to make the base part of DFS more generic and flexible are given. Also the general adaptation of the DFS at system level to reduce maintenance costs and increase robustness and reliability and to some extend to keep it conform with industry standards is mentioned. Finally the general infrastructure needed to cope with a changing system is discussed in depth.