Sentence 1: No, sir, not then, but I expect she did later.

Sentence 2: She didn't do it then, but she did it later in the day.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: It's not all fun and games for celebrity canines, however.

Sentence 2: Famous dogs don't get to enjoy all the time.
Is this second sentence entailed by the first?

Answer: yes

Sentence 1: For the next 19 years, Jerusalem was two cities.

Sentence 2: Jerusalem was divided in two cities for almost two decades.
Is this second sentence entailed by the first?

Answer:
it is not possible to tell