Sentence 1: The armored men tore the clothes from the two younger women leaving them naked and shivering.

Sentence 2: The men were embarrassed to be naked.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: Massachusetts put in a tough program in November 1995 and has seen its welfare rolls drop to the lowest level in 23 years.

Sentence 2: Massachusetts put in a lenient program in 1995, increasing its welfare rolls significantly.
Is this second sentence entailed by the first?

Answer: no

Sentence 1: Take all necessary precautions when participating in any outdoor sport.

Sentence 2: They all take precautions when doing outdoor sports.
Is this second sentence entailed by the first?

Answer:
yes