Thanks, blackcat. I do get what they're doing, and I think DD does too (you can suck ten items at a time over to the "boxes" side, or back to the "loose items" side) -- they are clearly trying to get kids to understand that one thing in the tens place (boxes) is the same as ten loose items. But asking the particular question they're asking just seems a bizarre way to try to acheive that goal.
I sat her down last night and walked her through a few examples on paper, and she looked at me like "yeah, duh" and I said that that's ALL that Dreambox game is trying to get her to do, and she was like, "OH."
I also like your strategy of doing it myself if I deem it unhelpful. I'll keep that in my back pocket.
