A small drop accumulates extra water from the cloud around it, depending on the temperature.
If it falls through a thicker cloud, it has more opportunity to accumulate.
If the cloud has updraughts inside it (is making thunderheads or whatever), drops can be dragged up and so make several trips through the cloud.
Hailstones do the same thing in colder air, and they can get much bigger than raindrops because ice is pretty strong, but water drops are only held together by surface tension.
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