Without seeing you file, I can't tell if the following might be your problem. However, I have seen a number of people hand-filing with this problem, so I thought I'd share:
One common error when hand-filing is not keeping the file in the same plane throughout the stroke. Some people tend to push down on the handle as they stroke, tipping the file like a see-saw. Even with that guide trying to set the correct depth for you, if you push down on the handle end, the other end rises up. This can wipe out the point that should be on the tooth, leading to the flat looking side plate shown in some of the teeth in your picture. In addition, If you are more prone to do this when filling left-handed vs right-handed, you'll file the teeth on one side differently than the others, causing the chain to cut on a curve.
When filing, be conscious of moving the file in a straight line. You can help yourself learn the muscle memory for this by putting the saw in a vise to hold it while sharpening. (I use a stump vise, or you can clamp the bar in a bench vise, as long as it leaves the chin free to move). This frees up both hands to hold the file. One hand on the file handle, the other on the fr end of your file/guide. Instead of providing all the power for the strike with the hand pushing on the handle, think about providing half the power by pulling with the hand on the other end. (While learning the feel, you may even want most of the power to come from the pulling hand.) That two-handed method helps assure that you have a smooth, level stroke.
This problem can happen whether you are freehand filing with a round file, using the clip-on guide or using the Pferd Chains Sharp CSX/Stihl 2-in-1 (which are the same thing). The roller guide does help avoid this, since if your file is not held in the appropriate plane, it will lift up off one of the rollers.
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Roller file guide.JPG
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