With the advancement of technology and the raising of massive amount of data, the used techniques for data security are continually a challenge. This paper contributes on identifying the gaps and evaluating security level on web portals hosted or managed by Republic of Kosovo institutions or businesses, whose data privacy and security could be a big business concern. The results have been obtained from real case scenario, where 25 security researchers have contributed in white hack activities. These activities, were part of a one day conference called. “The DAY when hacking is legal”, held in Pristine.