Sentence 1: The sad fact of an extended life span is that you get those extra years tacked on at the end, extending your frailty and neglect, not added to your 20s, extending your time in ersatz anthropology classes.

Sentence 2: Having an extended life span is something many people dream about.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: In her 18 years with him, she had never once heard Dole say, 'Here's what we're doing.

Sentence 2: In 18 years with him she never heard Dole say "Here's what we're doing" or "How are you?".
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: Julius looked at him and judged it wise to say no more.

Sentence 2: Julius figured that it wasn't a good idea to say anymore.
Is this second sentence entailed by the first?

Answer:
yes