To get the messengers to trigger, try going to see your companions, hang around them for a minute or so. If nothing happens, move on to the next. You should eventually encounter a messenger talking to them. Then go see the person on the other end of the convo. Say you find a messenger talking to Dorian, who says something about Josephine, then go see Josephine next to hear the follow-up.
It's very finicky. I do it when I'm waiting for resource collection quests to finish.
What do these messengers even look like? How do you identify them?
I've put nearly 300 hours into the game and I'm pretty sure I never saw them once.





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