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From defines.lua de jure assimilation toggles: will only assimilate duchy titles which contain the assimilating Kingdom's capital or border existing de jure land of that title
 
But not if a vassal kingdom is held by a vassal for a 100 years, then it won't drift, Bravoos didn't drift into the north, after being held by a vassal of mine for a 100 years? Is it if I hold the kingdom title?
It must be fully controlled to drift