OK...
DS is not yet good at looking at markers and knowing that there are XX markers there. He's getting better at the number rack, with the red and white beads and can generally recognize lower numbers, but not numbers >5 on two lines or larger numbers in general.
Two of the games he was stuck on were the type where they quickly flash a picture of the number rack and he has to click on the written number of it. The other one was adding to 10, but the numbers were represented by dots in various ways (e.g. three rows of two, plus a single dot to be 7). He can't really recognize what those are without counting the dots, so it would take him a long time and he would get frustrated.
After scouring the FAQ, I learned that getting the same games over and over has to do with not finishing the game. The software doesn't know where to "place" him within the curriculum if he doesn't finish it out.
So we sat together and worked through these hard ones. I explained that he just had to finish, even if he got things wrong. I help him work things out that are "too hard" and he cleared a few games, so it boosted his confidence again.
I'm often either next to him or nearby to help if he needs it. I wish he'd be more independent....
