Have you ever tried offering Tito more than half a cup? The only reason I ask is to see if he would really eat it all up or if he'd eat his portion then maybe come back later and nibble on it throughout the day.

I am able to free feed all 8 of my cats with no problems. I do know that some cats will overeat when free fed though.

Its also a little sticky since he is on adult food and Sophie's on kitten.

I don't know. I'd try mixing up some adult and kitten food together and then free feeding them both on a weekend when you can closely monitor who is eating what. That might make your decision of what to do easier.

If it looks like Tito is eating too much, you could always just take the food away again. I bet once he realizes the food is staying out though, he won't eat as much. My cats like to eat little bites here and there all throughout the whole day.