The spray skirt should not be at all able to exceed the power you can generate with arms and/or legs. A few things you can do:
1) Place your hands on the boat just behind your hips and push down. This should easily break the skirt free.
2) With above, extend your legs against the foot braces and simply push. This should also be sufficient.
3) Lean forward toward the front of the boat and push down with arms against boat just below the coaming. Extending legs vs. the pegs should facilitate this exit as well.
As with all things kayaking, practice until you find the solution that works for you. I haven't seen this happen, but I can certainly imagine that the pull for releasing the skirt may fail over years of use (if any will fail, it will be one of my old ones that I sometimes still use). I've tried all the above with skirts new and old and they all work. In truth, I don't even try to grab the loop since these methods all work quite well and are much faster.
Still, there is something to be said about putting an easily grabbed object on the skirt pull so that it is both hard to leave in the boat and easier to find when you need it.
EZ-Dock modular docks
Canoe / Kayak Anchors
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