What are your best stories about obsessively pursuing a GM's side-content unrelated to the main quest?

One of my players brought a class he saw on Homebrew wiki, a detective. So I shipped out a quick mysterious case for him to solve.

Long story short, they ended up finding out that one of their party is related to their favorite Artificer NPC, and they went to ask for more clues. NPC is as surprised as they are. So the party goes to talk with the adoptive parents of the ranger. And they show them the basket, the blanket, and tell them the story about a hooded figure leaving the basket on their door step. I put lots of clues in this story that would lead to the magician's tower they left before meeting the detective and the wizard living there, but no, they had to roll 7 times each to figure out what was that fucking basket made of and where the wood came from and who made it...

/r/MrRipper Thread