I often smoke GH Kendal Dark and Dark Birdseye in shag cut among others. I find that they need to be packed tight, but not with the usual way of packing a pipe. 

What I do that works for me is to take a clump and completely separate/loosen it up on a piece of paper, tray, whatever. Then I scoop it together, put it in one palm and roll it into a ball with my other hand until it’s somewhat firm. I can’t think of anything to compare the firmness to other than if you have ever squeezed a commercially made non filter cigarette. The filtered ones are much more loosely packed. It should be tight but still able to draw air through with some resistance.

The ball/clump should slide into the bowl without much effort or tamping. Obviously the quantity of tobacco determines size so a little trial and error is needed until it becomes a habit. Also better to have too much and pull some off and roll it a bit more than to add for a more even result. 

Grab the ball/clump with fingertips and put it in the bowl. Light tamp only at this point. The rest is fairly standard pipe smoking. The drier the tobacco, the tighter the clump needs to be. I get the best results this way. Takes a little practice at first but easily picked up. Smaller bowls are better. 

By the way the method I described and use, used to be a common way of packing pipes for shag and ribbon cut many years ago (old codger times) and it’s also how I still pack true ribbon cut tobacco, just a looser ball. 

I take the tobacco and cut it with scissors to a ribbon . Then gravity fill . Pack it tight and if draw is good , fire up . No problems whatsoever. 

I have a few shag cuts among my basket… never smoked it in a pipe, though. I tend to use 4 Aces Turkish and Drum for careful blending with other tobacco for better tasting cigarettes. Yes… I smoke a few of those. Gets me out of my building at work every day! There’s another let’s say more particular smoker at work (our sous chef) who enjoys them, too. 

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