Sentence 1: I think so. But the German spoke with less than his usual confidence.

Sentence 2: The German was speaking about the war.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: Men in dark red armor, faces hidden by wide necked leather helms drove long pikes through the screaming men.

Sentence 2: They executed them for committing adultery.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: He had a new one too, Ca'daan could see.

Sentence 2: Ca'daan used his eyes to note the newness of his item.
Is this second sentence entailed by the first?

Answer:
yes