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If you try to assign them, they just leave again
now click on that dorm and EDIT, Use the + icon on the bottom. Now ADD your berry planter. or scriptorum, later the kitchen same way. Now that dorm will staff the connected industry.
was having this problem for a long time, seeing sporadic success and then failure for no obvious reason
what I have found works for me 100% now is
(1) pause the game at any speed which stops the bug where it closed the people list on you
(2) click the monastery-type building (herb garden, scriptorium, anything) that you want to staff
(3) click the plus sign, choose from the unemployed and click their plus sign
(4) it will add the person
(5) to add a second person, either click the same building again which will cause its window to change a little (become longer or shorter) OR click a different building and reclick your building
(6) repeat steps 3-4
(7) repeat 5 again if needed
you can also click a different building as well instead of clicking the same building over and over again
the point is that the bug in adding people is avoided by seemingly cycling the building's panel; also, if your initial add is unsuccessful, try cycling the building's panel to get past the bug - sometimes it doesn't work during the first add which always made me think there was a game prereq stopping me which turned out to not be the case