Winter Squash Learning Curve Questions

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My first year growing winter squash. I experienced that on a vine I will be many small squash (having bloomed and then continued growing) yet only on will survive and the other ones wrinkle up and wither. (Attached are pictures) Is this normal? Or do I need to be providing more water or nutrients?


Appreciate any feedback.
 

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It is a pollination problem. It is normal as not all female blooms correctly pollinate or fail to pollinate due to factors such as few pollinators, insufficient pollination and weather. It is getting very very late for squash as all squash cannot withstand frost or cold weather. One plants winter squash at the same time he plants summer squash. Winter squash takes much longer to ripen and will store for a long period of time whereas summer squash cannot. Winter squash, depending on the variety is usually harvested in either late summer or fall, thus the name winter squash.
 
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Your squash plant will produce far more flowers and fruit than it has time and energy to ripen. What growers do is cut the vine after it has 4-5 fruits on it so that all the plant's energy goes toward ripening those.
 

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