This perk does not function in most areas that would be seen as artificial, as it suggests. The Gobsquat, sewers, ruins, western barrows, and inside of many 'city' QAs do not take it into account at all. It also does not work in interior areas which would also be fitting for it.
Still happening.
So many of these things are not a city.
Works fine after every reset until the main gate area is entered. After entering that area it no longer functions at all. It only happens after entering this area specifically.