Will Ivy League schools view my application negatively if I take the SAT more than three times?
Ivy League schools don't provide strict guidelines for the number of times you should take the SAT, but I would recommend that you avoid taking it more than three times.
In our blog article on how many times you should take the SAT, we say that you shouldn't take it more than six times. That's fine as a general rule, but many elite colleges, including Yale and Cornell, ask you to send all of your SAT scores. It might look like you didn't take the study process seriously (or were way too obsessed with earning those last few points) if you sat for the test more than three times. Also, these schools don't want to admit kids who are way too focused on standardized testing and not focused enough on other aspects of their application that show depth of character and strong academic/extracurricular passions.
Taking the SAT more than three times won't necessarily ruin your chances at Ivy League schools, but you'll look better if you avoid over-testing. Be sure to check out the average scores at the specific schools where you're applying to get a better sense of what your target should be. Here's a whole article detailing what a good score looks like at these elite schools.