The soil needs to be watered deeply each time. Shallow waterings, which is what it sounds like you're doing based on you saying that you water "multiple times a day", are bad for plants as it causes them to develop a shallow root system. After you water, check the soil a few inches deep to see if it's moist. If it isn't moist then you need to water more.

And before you water you should check the soil a few inches deep to see if it's dry. If it's dry, water. If it's moist, wait a day or two before checking again.

Rodney

I sink a plastic bottle into the soil to water. Besides achieving the purpose of deep watering, it also keep the top soil dry. Bugs like to lay eggs into wet soil and the bugs can move well inside. They could eat roots to make a plant not grow well. Once the baby bugs are gone, then the plant can grow well again. Just in case there are cutworms eating the roots, you can dig around the plant a few inches deep to remove the possible cutworms and wireworms. You can also lay traps to remove other insects like flies with soya sauce and oil mixture.

Multiple waterings a day? That doesn't sound good at all. I give mine a good deep drip watering in the evening and that's it.

I learned my lesson with overwatering tomatoes years ago. I was watering them every day and the brown leaves looked like they needed more when they actually wanted less.

Squash in my warm dry climate (California) need to be watered every day but multiple times would probably result in root rot among other things. Don't worry if the leaves shrivel in the day from the heat. No amount of water will prevent that.