It appears that the toolpath type may be related. It seems that different types of toolpaths that use the same tool will prompt. Two paths of the same type don’t?
tool change bug.c2d (728 KB)
Path POCKET 1 uses an endmill, everything else uses a 60 deg V Bit (tool #1002).
I get tool change prompts for
POCKET 1 → VEE 1 (expected - change from endmill to V bit).
VEE 1 → 2 (V Carve / drill path)
2 → 3 (drill path / V Carve)
4 → 5 (V Carve / drill path)
5 → 6 (drill path / V Carve)
NO prompt for
3 → 4 - (V Carve / V Carve)
EXPECT - Only tool change prompt should be the first one