“cunning.” The Hebrew word can have a negative or positive meaning: crafty or prudent. Here there is an element of both. They did act deceptively, but it was to save their lives.
“wineskins.” A “bottle” or container made from animal skin. The Hebrew reads, “torn and tied up.” It is likely that the skins had torn on an extremity and then that tear was tied up.
[For more on skin-bottles, which were usually made from the skins of goats, see commentary on 1 Sam. 10:3.]