Vinyl liners tend to lose their elasticity over time. If you keep the pool full, everything's fine. But if you drain it, the liner may draw up, and then not be able to be restretched.
If your liner is more than 3 - 4 years old, you may want to consider replacement. You can try draining again, during hot SUNNY weather, and see if you can stretch a hot liner back into place.
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