A set of segments in the plane may form a Euclidean TSP tour or a matching, among others. Optimal TSP tours as well as minimum weight perfect matchings have no crossing segments, but several heuristics and approximation algorithms may produce solutions with crossings. To improve such solutions, we can successively apply a flip operation that replaces a pair of crossing segments by non-crossing ones. This paper considers the maximum number D(n) of flips performed on n segments. First, we present reductions relating D(n) for different sets of segments (TSP tours, monochromatic matchings, red-blue matchings, and multigraphs). Second, we show that if all except t points are in convex position, then D(n) = O(tn^2), providing a smooth transition between the convex O(n^2) bound and the general O(n^3) bound. Last, we show that if instead of counting the total number of flips, we only count the number of distinct flips, then the cubic upper bound improves to O(n^8/3).