Itachi saw the flash of surprise and wondered why, if he were such a horrible brother and friend to people, anyone wanted to spend time with him.

"It's better to fail at the genjutsu portion than to figure out you're lacking when your life is on the line," Itachi responded neatly. Yes, he intended to be harsher than necessary with his genjutsu to make sure the children passing through were more than competent. It wasn't as if he would be the only one casting genjutsu, so even if he failed everyone, there would be some who passed.

"I'm sure he will place you somewhere your skills will be the most helpful," Itachi said, when he was actually sure Obito would put Sasuke somewhere that he would learn the most possible.