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If you want to make a question related to possession, when is it preferable to use Чей/Чья ...? and when is it better to use Кого...? ? Are both options grammatically correct?

Thank you!

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Чей/чья is the only one you can use here. Кого in a possession-related question would be as much of a solecism as "of whom" instead of "whose".

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