The classifier is returning a set of confidence scores, so if the shape you drew probably had a high confidence of both cookie and moon. (in fact if you draw it, and click on it in the endgame screen you can see some details what it saw in the image). We are not hinting the classifier what your task is, so we try not to bias the classifier. Jonas (developer behind quick draw)

Sounds like that drawing satisfies both criteria. (shrug)

So it's not really "guessing", it's just seeing if my drawing matches a predetermined bank of answers? Makes sense, since one time it asked me to draw a "police car" and before I had even finished drawing the chassis of a normal car it had already guessed "police car" and moved on.

It's probably assigning a number of possibilities with a confidence rating, and as soon as the confidence rating is > than some percentage of what it's asking you to draw, it says it.

I'd say it's "guessing" from a predetermined (rather small) bank of answers, since the same guesses appear over and over again.

it's correct that we have "only" trained it on a couple of hundreds of classes, so it will only guess from that dataset.