Using the bag purchased from craft brewer and grain crushed by craft brewer (default crush, didn't ask for anything special) I get wort pooling above the grain in the bag while I am lifting it. However it all drains out in a predictable fashion starting with a fast drain and finishing with drips some times later.
I also find that twisting the bag can give it an all-over squeeze. If you have the bag hanging just twist it around until it's nice and tight and wort will come out again. Probably easier than squeezing it the normal way and probably less likely to let crap come out of the grain.
so did i(all from craft brewer).........i also was twisting until i did the method i have mentioned above..... try it, no more twisting needed!