Flip-sort is a natural sorting procedure which raises fascinating combinatorial questions. It finds its roots in the seminal work of Knuth on stack-based sorting algorithms and leads to many links with permutation patterns. We present several structural, enumerative, and algorithmic results on permutations that need few (resp. many) iterations of this procedure to be sorted. In particular, we give the shape of the permutations after one iteration, and characterize several families of permutations related to the best and worst cases of flip-sort. En passant, we also give some links between pop-stack sorting, automata, and lattice paths, and introduce several tactics of bijective proofs which have their own interest.