A very common one [Linked Image]
Almost every power strip or extension cord I see around here has that problem. Sometimes the cord grips are useless right from the beginning, sometimes they're cheap plastic and break, or the people are just not capable of using them properly. Yanking the plug out of the receptacle by tugging on the cord adds to the problem, especially with Schuko plugs that usually grip pretty tight.
The Italian plugs I know are pretty spacious inside, so there's absolutely no reason for doing this, apart from sloppy work or cheap materials.
The picture definitely looks like it's taken in Italy, but why on earth is it labeled 220V? All receptacles there are 220V, apart from red CEE ones.