I talked to dude (Elder Mossbern) in the screenshot before receiving quest, and when I went back and received quest, he can’t be “checked” after talking, he just stays as if I didn’t talk to him. Teleporting back and returning fixed it.
My guess is that it works for all of them and it related to the fact that I speaked with him before getting the quest.
Screenshort: https://imgur.com/a/EeBsjzx