In this new era of technology, it is crucial for a professional organization such as Universiti Teknologi Mara Cawangan Terengganu Kampus Kuala Terengganu (UiTMCTKKT), which in needs of managing yearly strategic planning, to have a reliable Management Information System (MIS) in order to work efficiently. Currently, there is no specific system used for the university to manage the yearly strategic planning and tracking its progress for reporting purposes. Hence, derived a problem where there is a lack of documents sharing and sorting system as currently the staffs only communicate and sharing the documents through the communication applications such as WhatsApp and Telegram. Furthermore, Ketua Pusat Pengajian (KPP) also needs to continually remind the staffs to make progress on the strategic planning before the deadline through the communication applications. In response to the problems, a Strategic Planning to Success (STRAPS) system is developed, where it is an online web-based system that incorporates the Plan-Do-Check-Act (PDCA) technique, as well as, the cloud computing theory. This theory and technique will be implemented as a concept for the development of the system. Additionally, a System Development Life Cycle (SDLC) Waterfall Model is used as a suggested method to guide the whole process of the development of the STRAPS system. Besides that, a system testing plan and evaluation from the thirty (30) respondents and two (2) experts also are carried out as a method to improve the functionality, usability and interface design of the system. The result of the testing, which is performed in an environment that closely resembles the production environment, is then being discussed in this paper to provide more reliable and efficient outcomes. It is an essential phase as it means that the system is well accepted and meets the specifications of the users and ready to go live.