Schools from all over the world are moving into the direction of using more e-learning, digital gadgets and BYOD (Bring Your Own Device). In the Estonian Strategy for Lifelong Learning 2020, the switch to 1: 1 computing in classroom is called "Digital Turn". The strategy relies on expectations that smarter use of personal digital devices will improve not only digital literacy of pupils, but also their academic achievements in various subjects. The Estonian government plans to allocate 47 million Euros of national and EU structural funds until year 2020 for this purpose. There is also interest in improving digital skills of school-leavers on the side of the industry, as the Estonian ICT sector expects to double the turnover within the next 4-5 years. The sectoral analysis estimated the need for 8000 new employees in ICT companies. To achieve this, the industry has supported various educational programs like the Look@World Foundation's Smart Lab project, Samsung Digital Turn project for schools, using Raspberry Pi-s at school supported by TransferWise, Microsoft's Partners in Learning projects and so on. Challenges for the digital turn are related to people's involvement (teachers, school leaders, students, parents, officers); resources (gadgets, time, salary, maintenance); promises (this is beneficial for improving the students' skills and competences and also is the only way); lack of analysis (act more, measure less). In this article we will study the Samsung's Digital Turn project applications for the schools 2014 and 2015 in order to understand what are the goals for the schools when they think of digital turn; we also have asked school ICT administrators, educational technologists and school leaders to list seven issues that come into their mind that should be death with in the process, and surveyed teachers of one school over a 4-year period, tracking the changes in using technology as well as learning and teaching. We will analyze the data to understand the trends and difficulties schools will face during this journey. This information is needed to train all other 450 schools that have not started their digital turn change yet, but are forced to act soon. The trends in digital turn projects will tell us the maturing process and goals that the schools have as opportunities and strengths while the list of difficulties shows the project's weaknesses and threats. Looking at one school over 4 years will help us to understand the change, especially the areas that have changed in teachers' practices. In the conclusion we propose a list of actions that can be used to meet the challenges that can ruin the digital turn for most schools. We also propose an area of measures where the digital turn is the most visible.