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So I've been running around between areas for quite some time, trying to get this guy to show up, and he never does. I'm of course referencing the messenger who apparently shows up when you enter the Tularean Forest after completing either the Riverstride or Caves Rescue quest (I did both).

Is there a specific amount of time I need to have passed before the messenger will show up and kick off the fight for the trumpet?
This question / problem has been solved by Thievimage
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Castrum: [...]
It occurs after 2 months dating from when you learnt about the war (when ambassadors arrive to Harmondale). You have only 1 month window to do the quest, after that the Judge dies and the plot goes on.
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Castrum: [...]
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Thiev: It occurs after 2 months dating from when you learnt about the war (when ambassadors arrive to Harmondale). You have only 1 month window to do the quest, after that the Judge dies and the plot goes on.
Thanks. I kept playing and eventually I got back to Harmondale and the judge died, so oh well.
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Castrum: [...]
Then you got something to remember about in the next playthrough ;)