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I'm confused with the meaning of "circumvent"

According to my vocabulary book, the meaning of circumvent is "to frustrate as though by surrounding" An example sentence given was, "Our hopes for an early end of the meeting were circumvented by the chairperson's refusal to deal with the items on the agenda."

However, another dictionary says the exact opposite, and said the meaning of CIRCUMVENT is "find a way around (an obstacle)". An example sentence given was, "the checkpoints were easy to circumvent".

So which is it? I'm really confused since I see how these two meanings can be used in the same situation with completely different meanings.

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In your example sentences, circumvent actually means the same thing—not the opposite. It's just that you're looking at the sentences differently, so it appears to mean the opposite.

Our hopes for an early end of the meeting were circumvented by the chairperson's refusal to deal with the items on the agenda.

1) The chairperson found a way around the agenda items (and your hopes).
2) Your agenda items and hopes were frustrated.

The checkpoints were easy to circumvent.

1) It was easy to find a way around the checkpoints.
2) The purpose of the checkpoints was frustrated.

In your question, you are using only 1) with the first sentence and only 2) with the second sentence. However, circumvention means the same thing if you switch points of view and look at each sentence from the same perspective.

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circumvent TFD

  1. To surround (an enemy, for example); enclose or entrap.
  2. To go around; bypass
  3. To avoid or get around by artful maneuvering

So you can avoid, go around, obviate, bypass, outwit, outfox etc. Definition #1 is a little used military definition.

Here is Oxford Dictionary and surrounding is not included.

Find a way around (an obstacle) ‘if you come to an obstruction in a road you can seek to circumvent it’

1.1 Overcome (a problem or difficulty) in a clever and surreptitious way.
‘it was always possible to circumvent the regulations’

2 archaic Deceive; outwit. ‘he's circumvented her with some of his stories’

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Circumvent means to bypass.

Lets say there are 2 points A & B. You wanted to go from point A to point B. There is a path from A to B. But you find it difficult for some reason.So you find another path around. And by going in that path is easy for you.

Circumvent means to go in another path from 1 point to another point rather than the usual path ,so as to avoid some problem.

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