The first move of the toolpath should be perpendicular to the axis of rotation. Otherwise you end up with a really big offset move at the beginning of the ramp-in which can result in the tool traveling backwards relative to the direction of the toolpath. This is because on the initial plunge move, we do not know the offset direction, so the Y offset is 0. The first move of the ramp is at close to 90 and needs almost a full tool radius offset. If you are doing a linear ramp at the start of a roughing operation, you end up with a full tool radius offset change on each ramp move.
The feature you are cutting should have no sharp corners.
Open profile sides should use the insert arc check box in the Stepovers tab.
Roughing operations create sharp corners on the inner stepovers if you use too large a tool. The default tool is always too large.
There is a limit on depth of cut with a given tool. It is related to the no sharp corners rule. If you are cutting a rectangular pocket, when the tool moves along one side, the Y offset is 0. The corner radius must be large enough that the tool does not gouge the next side wall when it finishes the current cut. The limit is: