@dankoenigsfeld
Hmmm, apologies but I don`t see a "bug" here, this is user use of Toolpaths.
In your original example yes, the Contour is considerably faster, however it doesn`t cut all the material away, leaves a small block at every junction, the Pocket takes longer but it does clear all the material away, do you want to have to go clear those leftover small blocks later by hand? Yes save machine time but then becomes more Labour Intensive ?
That is your choice as the Operator.
By far the easiest way to do it would be to use a slightly larger cutter, a 5/16 or 3/8 instead of a 1/4 actually does the full clearance of material in about the same time as the Contour not clearing it away, see the numbers below 🙂
Contour using 1/4in cutter = 13.264ft in 2.42 mins but doesnt clear all
Pocket using 3/8in cutter = 14.578ft in 2.47 mins and clears all (5/16 is almost the same)
That`s with Feeds set "like for like".
Summary, you are expecting the Pocket to clear all material away using the 1/4 cutter versus the Contour that is not clearing all the material away in the same time? This it cannot possibly do, IMHO your expectations are a bit "skewed" as far as your example is concerned anyway.
Either us a larger cuutter or run the smaller one faster, only options that I can see 🙂 🙂
Aplogies if this not what you want to hear 😞