As Jim says, put the bottom of the sleeping into the stuff sack first. Once I get it started, I use my fist to push it all into the sack. Then, I pull the draw string tight and the shape it to fit into the specific area of my pack. It depends on the pack and the bag/quilt as to where it goes in the pack.

Tango
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If you think you can, you can. If you think you can't, you can't. Either way, you're right.