As a foal, Zap Apple was always surrounded my dogs -Winona or Winona II (referred to as “Junior”) usually slept next to her bed, they begged for scraps at the table, followed her around the acres, and tried valiantly to rescue her when she was given a bath (usually by jumping in the water with her, and splashing everything in the bathroom). So when Winona II had her first litter, Zap was just excited to have even more dogs to play with -and even better, these dogs were smaller than her, so she could pick them up and dress them up in her doll’s clothes! Zap thinks they’re soo cute, but her mom doesn’t seem to agree with her for some reason.
Oh, and in case you’re wondering, all the pups are named similarly to Winona -Winny, Winnifred, Winola, Winchester… they
had Fluttershy ask Winona and later Winona II what they wanted their pups names to be, and they just really like the name “Winona”. They originally wanted to name all the puppies that, but eventually got talked around to (see, “bribed with treats”) just similar names.