The analysis of unintentional islanding in distribution grids with a large penetration of renewable energy sources is of increasing interest due to the recently introduced requirements of P/f and Q/V supporting capabilities of Distributed Energy Resources (DERs) and the wider frequency and voltage ranges, DERs should be able to operate with, before protection tripping. DER anti-islanding protections, if present, may fail to detect this grid transition and so uncontrolled islanding operation may appear. Since this operating mode may be dangerous for the electric network operation and may cause damages for the grid equipment, in this paper the increase of its risk due to P/f and Q/V droop characteristics of generators is addressed. Analytic results are initially derived for the steady-state unintentional islanding operation and then they are validated on a laboratory-scale grid setup. The proposed investigation will show that the risk of permanent unintentional islanding increases introducing P/f or Q/V droop regulation and that such risk is maximum including both the P/f and Q/V droop regulations, rather than only one of them.