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A well-known British writer has this:

[to question] how it might all have started

To my non-native English speaker ear this sounds a bit off; I'd have said

[to question] how it all might have started

Is there a difference in tone between the two variants that I might be missing? What sounds more natural?

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    There's a difference in euphony if not in practical meaning.
    – TimR
    Commented Jan 31 at 0:29
  • ... Yes, as Tim implies, the less logical-looking variant sounds more attractive. It's surprising that the Google 5-grams for "how it might all have" / "how it all might have" show that the less euphonic variant seems twice as popular.
    – Edwin Ashworth
    Commented Jan 31 at 12:35
  • If you think "all have started" goes together then you don't break it up with the word "might".
    – Stuart F
    Commented Mar 1 at 9:40

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… how it all might have started
… how it might all have started

A fine point of meaning. I have also considered a close variant such as:

… how it might partly have started
May draw attention to the various ways in which the matter may have started. Partly is acting adverbially on start

… how it partly might have started
May draw attention to the role parts of it played in starting the matter. Partly is acting in an adjectival manner on it

But this is straining to find nuances that, while possible in this variant, do not seem to work with your own example. I therefore suggest that there is no significant difference there.

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