I chamfer/rad with my cutoff thousands of times per week. the cutting block of my cutoff looks like this:
(.187 stock, .010 chamfer)
T0505 (iscar 2mm cutoff)
G0 X.21 Z1.00
(skipping over some code...sub approach, sync, chuck sub)
G1X.150F.0015(PLUNGE)
X.2F.02
W-.030(BEGIN OF CHAMF)
X.193(ABOVE STOCK)
X.187W.020F.0009(BURR PREVENTER/RAMP IN)
U-.020W.010F.0005(CHAMF TO OAL)
X-.05F.0015T0 (CUTOFF)
On one machine I use a NTK .060" wide cutoff that comes to a sharp point. This one is more succeptable to corner chipping. Ive noticed that sometimes when I touch off the tool it will move a couple/few thou so if you rapid too close to the stock it will hit and chip the edge. In that case I cheat my numbers a few thousandths and just change the nnumbers to something like this:
X.200(ABOVE STOCK) (CHEATED)
X.192W.020F.0009(BURR PREVENTER/RAMP IN) (CHEATED)
The other cutoff I use is an Iscar Tang grip 2 or 3mm cutoff that has a .004 corner rad. I strongly prefer this tool over a sharp point cutoff. It is extremely consistent with the cutoff chamfer/rad. I have put up to a .125 rad on the end of the part with the 2mm tool. In that case I did 4 plunges to clear stock so it was only cleaning up a little material on the final G2 move. Also you can push the iscar cutoffs a lot harder. I use .001-.002ipr with the 2mm and .0015-.003ipr with the 3mm.
So try a cutoff/insert with a small corner rad and you'll never have this issue again! (you'll have to cheat your cutoff numbers slightly as it is easier to do that than using cutter comp on the cutoff, in my oppinion)
CNC Product Manager / Training Consultant