I had the same problem you have with the Oregon unit.Thought it was me! I'm using the Granburg unit now and all is good.I use the Oregon version. I may be doing something wrong because when I try to file the cutters on the other side I'm not satisfied with the file's bite. Seems like the metal screw cap that tightens up one of the angle settings interferes too much. To counteract this predicament I take the chain off the bar and put it on backwards. That seems to do the trick so far. Have you experienced noticed the same thing?
Takes me close to 20 minutes I believe to get through a loop because of what I described above so I take three sharpened loops with me and change them while in the field. Since it takes me so long to file I do it at home as a sort of meditation exercise.