In the coming years, distribution grids will be progressively flooded by renewable energy sources (RES) that will be interconnected with the main grid through power electronic converters. Photovoltaics (PVs) are one of the most promising renewable technologies even for densely built‐up areas where space problems are inevitable. The high penetration prospect of PV facilities on low‐voltage distribution networks raises questions regarding the necessity of advanced functions that will enable electronically coupled RES to support the operation of distribution grids and to enhance their reliability. In this context, the objective of this study is to investigate the effectiveness of various islanding prevention measures installed in commercial PV inverters, when multiple inverters are operating in parallel with a low‐voltage distribution network (LVDN). Extensive experiments were performed under various PV penetration levels, linear/non‐linear load and over/under voltage and over/under frequency conditions, as well as for various values of total harmonic distortion of the mains voltage. Further to the primary statistical analysis, the results were analysed in depth by advanced mathematical methods such as box plot and cluster analysis. The findings of this study indicate that commercial anti‐islanding techniques present a high probability of failure in the case of multiple PV units at the same point of common coupling, calling for new and more advanced algorithms.