The Common Agricultural Policy (CAP) reform of 2014-2020 is characterized by a strong mandate of Member States regarding the 1st Pillar. This paper’s objective is to elucidate the possible impacts of Italian choices on direct payments and their coherence with the specific objectives of the CAP, which was established by the Expert Group on Monitoring and Evaluating the CAP (EGMEC): food security and sustainable food production. Thus, an online survey was disseminated among Italian CAP experts in the spring of 2015. The results from a sample of 25 respondents show that Italian direct payments may positively contribute to viable food production by improving agricultural competitiveness. In addition, the combined effect of general direct payment schemes and Italian choices is to ensure sustainable food provision or, at least, to successfully allow the exploration of this new route in CAP history, which most likely represents future challenge for European agriculture.