That windmill in the foreground with the blue door is where they hold second breakfast.

Frodo B. and Samweis G. were, according to our sources, recruited by a Valinor national to export magical waste into enemy territory.

I mean… in fairness, it wasn’t going to last.

So since their war-virginity was about to be stolen from them anyway, he made sure to get in there first, for his own benefit:-).

Hobbits are the f-22 of fucking-with-sauron tech. He can hardly detect or manipulate them, compared to the other races, and they are literally small and sneaky around his minions who are generally not built to handle that