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Examples:

"I'm going to study until 8PM" Is he going to stop studying at 8PM sharp or 8:01PM?

"I'm not going to study until 8PM" Is he going to start studying at 8PM sharp or 8:01PM?

"I'm working until Friday" Does he stop working after his work on Thursday or Friday?

"I'm not working until Friday" Does he start working at Friday or Saturday?

"The kidnappers have given us until October 11th to deliver the documents" Do they need to deliver the documents before it hits October 10th or 11th?

From other similar posts, I learned that until is mostly exclusive but it can sometimes be inclusive but how do I tell exactly?

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The first two questions are pointless. No one saying those things about 8 PM intends the precision implied in the questions. The meanings sought aren't implied by the word "until".

The two questions about Friday aren't pointless, but the meanings are ambiguous until more information is supplied.

Examples that resolve ambiguity:

"I'm working until Friday, so I can't travel until Saturday."
"I'm working until 5 PM Friday, so we can't party until 6 PM."
"I'm working until Friday, when I'll be able to sleep all day."

An ambiguous statement clarified by questions:

"I'm not working until Friday."
"So, do you mean you won't start working until Friday, or do you mean you aren't going to continue working all the way up to Friday?"
"I mean I'm quitting Thursday morning."

As they stand, without a framing context, your statements are all under-determined. The meaning you're searching for isn't there.

The only example that I would call unambiguous is the one about the kidnappers, but if I had to meet a ransom demand, I would certainly ask "What time on the 11th?"

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  • 1. Can you please rephrase the first paragraph? I'm not sure I follow. And isn't it fine to say those sentences in speech? 2. So basically, without proper context or more information, it's hard to tell if until is inclusive or exclusive? In my third sentence (without providing more info), he either finishes on Thursday or Friday? 3. Can you give some examples using "until" where the sentences are not unambiguous? – Max Jun 3 '20 at 1:02
  • 1.Tell me what you didn't understand about the first paragraph. 2 "Until" is neither inclusive nor exclusive. The information about what is intended is either in context, or in other information in the sentence. 3.You have given examples that are ambiguous, and I have already given examples which aren't ambiguous. If you want to examine the question further, I suggest you find an example of "until" at google books that you actually don't understand, where it makes a difference, and put it up as a question. When I say "makes a difference", I mean something other than 8 vs. 8:01PM. – Jack O'Flaherty Jun 3 '20 at 2:15

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