<Snipped quote by VeyrinDay>
I'm a bit confused by where this would come into play IC, as there was no initial ambush would have brought about the need for this, nor has there been any potential for ambush at your locations.
Additionally, considering the low roll total of 4, she would not take note of any potential ambush even if there was one. At best her passive perception of 14 would be applied for any potential danger incoming.
Did you have something specific in mind for how to otherwise apply this IC?
what I imagined was that Tenria would observe the activity in the market. Were the traders really free entrepreneurs or do they have to regularly pay protection money? To whom? Was it authorized? Were there any enforcers of someone with power other than the legal authority? How dangerous were they? How would these people see outsiders? How about rich outsiders?
In my idea, a natural 20 of this would make Tenria able to assess Itylara's authority in Sarlano, and if she's not that powerful, Tenria might be able to identify the power struggle within the city. In technical terms, any travelers wandering with Tenria would never get any ambush-type encounter for a mile around the city's border after Tenria managed to do something with the information she got from her observation.
Yes, I got four. That can mean that Tenria failed in her observation. But she can also fail miserably, like an enforcer or a bandit noticed the signet ring on Tenria's hand. This can prompt the further encounter to have more creatures, but with higher probability to prevent using bribe/persuasion.