Crew Agent Making an Executive Decision when Tool not available?

Can someone clarify what happened here for me with the Trip Planner Example?

The first thought is “do I need a tool” answer: Yes, then the tool fails.
So the second time it thinks “do I need a tool” the answer: NO.

Did the tool failure the first time influnced the outcome the 2nd time when it said No? (If so that is pretty amazing.)