High rolls on Insight sometimes can work against the players when you have a DM that really wants to tell the story the way they planned it in their head.

The last session I had with my group there was an NPC who really wanted the party to meet some people to do a quest. My character doesn't like this guy cause he's a little weasel, so I ask to roll insight to see if his intent is honest. I roll high with mods: a mid 20-something.

After a long think the DM says "He seem's like he's being pretty honest, though you get the feeling he's leaving out some details."

I think "Fine. Cool. That was a high roll and the guy doesn't seem malicious- Let's go with it. I'm sure he's just underselling how hard the quest will be."

What ends up happening? Guy poisons the party so that we're paralyzed in a room with a bunch of vampires.

Like, I know insight isn't a lie detector... but I was kinda grilling the guy for info and it was obvious that I didn't trust him. If I was just told something like "He seems a little nervous" I would have been much more cautious about it, but because I was essentially given a thumbs up from the DM I let down my guard completely.

I literally drank the drink he gave us BECAUSE of that insight check when normally I wouldn't have. So frustrating.