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push harder, nancy
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It helps to push in the right place, too. Push just in front of the clip, so your thumb barely misses rubbing the clip. Sometimes it helps to shake a clip a little bit, because the phosphate coating on the clip can grip the case rims pretty tightly - shaking helps loosen them up.
At Lackland AFB's range, where the Basic Trainees get to actually touch weapons, it's not uncommon to find clips that are actually ridged - the kids push at the shoulder HARD and the brass bends the clips pretty badly. Sad to say, but Combat Arms doesn't do well by those kids.
Edit to add: And I've been a believer in the StripLULA for a very long time. I'm gonna have to pick up a Version 2 just to see what's different about it. I've used mine both with and without clips (you just have to avoid spilling the loose rounds), and it makes every single clip, new or old, tight or loose, load the mag almost as easily as "pouring" rounds into it.