Punctuation

Q. When a question introduces a list, should you use a question mark or a colon? Or both?

A. First, don’t use a question mark immediately followed by a colon, or vice versa (neither :? nor ?:); instead, use the stronger mark. Assuming a direct question, the question mark is usually stronger.

Which fruit would you be most likely to recognize by texture alone?

banana
apple
blueberry
cherry
pineapple

A signal like “the following” can be helpful in such cases: “Which of the following fruits . . .”

If you incorporate the list into a sentence, the question mark can follow the last item.

Which fruit would you be most likely to recognize by texture alone: bananas, apples, blueberries, cherries, or pineapples?

Especially for shorter sentences, a comma can be used instead of a colon to introduce the list.

Which fruit do you like best, bananas or pineapples?

but

Do you prefer apples or bananas or blueberries? [See CMOS 6.67.]

[This answer relies on the 17th edition of CMOS (2017) unless otherwise noted.]