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Would have had to have been doing, e.g.:

For him to have become a threat in the teachers eyes, he would have had to have been exhibiting severely bad behavior all the time.

Would have had to be doing, e.g.:

If I hadn't finished my work at school, I would have had to be doing it at home, whilst everyone else could have been doing something fun.

Are these grammatically correct despite being so clumsy? Keeping in mind that in both sentences there should be maintained a sense of progression. So it is an ongoing action.

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  • Yes, they are grammatical despite being so clumsy.
    – Alan Carmack
    Commented Sep 30, 2016 at 14:55
  • These sentences are grammatically correct, but not natural. In both cases it would be more natural to use a simple infinitive instead: to exhibit rather than to have been exhibiting and to do rather than to be doing. Other parts of the sentences are not natural either, for example severely bad rather than extremely bad. books.google.com/ngrams/…
    – JavaLatte
    Commented Oct 18, 2016 at 11:35

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Grammar is like water, in that speakers will take the path of least resistance. Things begin to become ungrammatical, or at the very least unidiomatic, when the water starts flowing upstream, as it does in your examples.

I suspect most native speakers would use must there, to avoid would have had to have been:

For him to have become a threat in the teacher's eyes, he must have been exhibiting severely bad behavior.

That's not possible in the second example. My AmE ear tells me to avoid "would have had to be doing" and to say something like this instead:

If I hadn't finished my work at school, I would have had to continue working on it at home, while...."

or simply, would have had to finish it at home, as the semantics of the sentence don't demand the continuous.

Maybe something like this:

If I hadn't reached him before he left the office to discuss that emergency, I would have had to be phoning him repeatedly until he answered the call on his mobile phone.

But even then, many native speakers would find would have had to phone him repeatedly sufficient. As long as there's some indication of repetition, such as "repeatedly" or "again and again", it isn't necessary to use the continuous tense. Absent the adverbs, then would have had to be phoning him until... is more viable.

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