I don't find this sentence very natural. Normally you would say "He should know it by now". This has the two possible meanings that you describe.
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IvanhrI don't have any problems with 'should have known by now' but I find the 'it' after the phrase very unnatural. For exampleI should have known by now that you are an avid runner.Personally, I think I would, by preference, still use "I should know by now that ...", but I agree that this one sounds less unnatural. I think there may be a crossover with the
IvanhrI should have known by now that you are an avid runner.Then, does this "I should have known by now that you are an avid runner" mean two meanings?
pructusThen, does this "I should have known by now that you are an avid runner" mean two meanings?1. I know now that you are an avid runner.2. I didn't know that you were an avid runner until now, but it's not good that I didn't know until now.This sentence would be understood to mean the same as "I should know by now that..." (which for me is preferre