Free Hand, often thought to mean the pipe was made with no particular design in mind, actually means that you need a free hand to smoke it. (I kid)
They don't 'sit', although, they will clench, as most are offset for balance.
I've got a cob and a briar freehand. Their bowls are about the largest I smoke, and do tend to mimic a Dublin's taper inside.
My briar is a Savenelli gifted by a forum member that has been in my rotation for perhaps a bowl a week and gets better with practice. Its drilling and bowl configuration have the draft almost below the bottom, which gets fairly narrow there.
I've learned to leave some space when loading. Often, a bowl will be left for delay gratification and re-lit and smoked for several times.