Pool Pillows for winterizing - what do they do?

Protects from damage caused by the accumulation of rain, snow, and ice. The pillow into an ice compensator: when the pressure builds up due to the pool freezing, the ice expands inward towards, and compresses the pillow instead of outwards into the pool walls.

If you don't use a pillow, the pressure from the ice pushing on the walls could damage the cover, liner, and the walls themselves.

Inflate the pillow to around 70% of its capacity

A 4'x4" should be just fine.
 
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Many people get mad that they pop- but that’s usually because they over inflate them so they pop when they do their job. Their purpose is literally to get squished - like a gizmo but for the whole pool- not to raise the cover so water doesn’t accumulate as many believe.
I don’t use one & things have been fine but I don’t live in the great frozen north lol 😂.
Although my pool has been frozen solid a couple times I am generally able to keep most precipitation off my cover for the bulk of the off season.
 
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These answers seem to imply that I need to keep the top of the cover more or less dry. Is that correct? We often have a foot or more of standing water in places on the cover, which we drain before opening in the spring. Is there a reason to drain the cover often?
 
I consider pillows a right of passage. Most start with them and almost everyone eventually gives up, frustrated that they popped. Eventhough its their own fault as said above from overinflation, they eventually have enough friends telling them not to use them and they go without. Nobody ever goes back to pillows once they've gone without. :)
 
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These answers seem to imply that I need to keep the top of the cover more or less dry. Is that correct? We often have a foot or more of standing water in places on the cover, which we drain before opening in the spring. Is there a reason to drain the cover often?
The water on the cover displaces the water in the pool. A little helps with the wind for some people but alot can cause water to go where you don’t want it to go (out of the skimmer) & means you have to refill more in the spring.
I like to keep my cover as clean as possible so removal isn’t so disgusting or arduous & because of mosquitoes 🦟 as that’s not chlorinated water.
I use a leaf cover on top & dump that off when the bulk of the leaves have fallen & again before opening.
I use an automatic cover pump to keep the cover dry- we get alot of rain in the off season. It gets removed in freezing temperatures.
I also don’t want to risk the weight of the cover pulling on my rails & wall or getting heavy & ripping releasing funky stuff into my beautiful oasis.
 
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I use a pillow. I have used THE SAME PILLOW FOR 10 YEARS. In freezing weather. I do not understand how people keep popping them. I fill mine all the way (it is also a huge pillow, like 6' x 4'). I do so because it leaks out of the fill hole - it is a pretty pool seal, so by spring it is down to about 80% capacity. The grommets on the ends have ripped on it, but I just bunch it up and tie on my ropes.

As for my method. During the fall, I try to keep water off of the cover by pumping it off. Keeping the cover dry lets leaves blow off. Once the leaves are down, I let some water collect, but not enough to push the water out of the pool. Sometimes that is not possible (lots of snow, and a non-frozen pool for example) but I do try.

Once spring comes around, I keep the water off the cover again - avoiding mosquitoes, frogs, and whatever else likes to grow in there.

While it may not be it's "official" reason, having a pillow in the middle makes pumping off water a lot easier, by keeping it near the edges.
 
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