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In a longer, complicated sentence where one repeats the subject, verb and object, does one invert only the first svo or all of them to create a question? Or maybe both cases are correct with a slightly different meaning?

The example which motivates my question is:

"Could You estimate, very roughly, when You could send the samples?"

"Could You estimate, very roughly, when could You send the samples?"

My boss insists to use the first form, but he is French native speaker... so let's say that I don't trust his English instincts too much ;)

  • Il a raison. Look at the simplified 'Estimate when you could send the samples, please ... you don't have to be spot on.' Or switch to *'Can you be sure when will you be free?' (the asterisk labels as ungrammatical) – Edwin Ashworth Nov 16 '17 at 10:28
  • You boss is right -- the first one is correct. Unlike main clause interrogatives, subordinate interrogatives (embedded questions) don't normally exhibit subject-auxiliary inversion. Compare the main clause interrogative "When could you send the samples?", which does have inversion. – BillJ Nov 16 '17 at 10:38

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