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Upon visiting different shuls, from various elements of society, it pains me to see many fine Jews who are definitely donning their tefillin wrong and many others about whom it is hard to tell, especially when they have receding hairlines. This being said, I sense an improvement over the years, but still even some learned people get it wrong. Presumably, then, they are having problems applying the halacha, not realizing, especially after their hairline receded, where the cutoff point is. We will focus here on tricks to figure this out.]
Bemare Habazak - Rabbis Questions (652)
Rabbi Daniel Mann
621 - Ask the Rabbi: Giving Ma’asrot to the Intended Recipients
622 - Ask the Rabbi: How to Tell When Your Tefillin Need Adjustment
623 - Ask the Rabbi: Using Replacement Mezuzot When They Are Being Checked?
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Now, a little review of the anatomy of a normal human head. The skull is highest towards the back of the head; it then gradually slopes down. Near the front of the head, the slope increases, and then turns into a "cliff" (i.e., the forehead). The hairline ends at the end of the gradual or in the midst of the increased slope. No hair (except eyebrows) is rooted in the forehead.
Based on the above, the following are signs of misplaced tefillin. If the end of the tefillin looks like it is "hanging off a cliff," it is certainly much too far forward, as a line drawn down from the end of the tefillin would hit the forehead or even the nose. Because of the increased slope, there may be a little space between the bottom of the tefillin and the head. However, if there is too much room (i.e., a finger fits in comfortably), it is very likely not in the right place.
Another sign is the tefillin’s angle. The angle is determined primarily by where the tefillin are fastened to the head by the straps – at the back of the tefillin. Generally, tefillin in the right place will be upright with only a slight downward slant. If the tefillin has a serious downward-facing angle, it is generally (unless one has a rounder head than most) too far forward, so that its rear is where its forward part should be (on the steeper slope). Thus the tefillin’s front will be too far forward, unless the tefillin are very small.
A final sign is the kippa. With average size kippot and tefillin, there should be little or no room between the two. One with a particularly large kippa or who wears it more forward than most will have to move the kippa back.
When I look around many of the shuls I regularly daven in or visit, I see many too many people with apparent (or definite) problems in this regard. Among the older generation, I would estimate that the problems are in well above 50% of the people. As I HATE correcting people (and most hate being corrected), I am torn as to when the rectifiable problem is clear enough to halachically/morally require me to do the uncomfortable. The following limud zechut decreases the problem. Most people put the tefillin at a certain position and push it forward in the process of fastening. Thus, some of those who keep the tefillin too far forward had it in the right place for a few moments after the beracha (so that it is not l’vatala) before the fastening was complete, and thereby may have fulfilled the mitzva for that short time.
More people should learn how to shorten the circumference of the head strap, which is necessary for the tefillin to stay in the right place. You are invited to visit me or ask a sofer. It may be easier to Google search: "youtube tefillin head adjust." Then, you can help yourself and your friends.

Bemare Habazak - Rabbis Questions Ask the Rabbi: Omitting Tachanun in Selichot in the Presence of Simcha
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