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It depends on both the policy of the college and whether you self-report through one of the college portals like the Common App or Coalition App.
If a college asks for all your test scores, then you oblige them. If they only want you to report either your 1.) Superscore or 2.) Highest SAT, then do that. On the Coalition portals, they ask you "how many times did you take the SAT?" and then "What is your highest score?" Then you have to fill out the English vs Math part and give the test dates of the highest scores. On the Common app, it asks "How many SAT tests to you wish to report?" Then you tell them and then it asks "How many future SATs you will take?" Then you fill out the Reading vs Math. So on Coalition, you disclose total Tests and on Common App you decide how many to disclose.
In some cases, it gets more nuanced and complicated. At U.Washington they are test-optional but when reading your app, are test-blind unless your SAT is above the 75% percentile. Then they process those differently. Maybe those are applicants that are considered for Merit Awards, something like that.
All the literature I've seen from colleges weighs in the direction that you will not be penalized for taking the SAT multiple times. However, some CV posters will disagree with that and chime in that there is a certain maximum number like 3, or 4. I think if you are at 1200 and keep improving 50pts each test and now you are at 1450, then keep going. But if you are at 1450 and the next one is 1420 and after that 1460, then you're kind of stuck at the mid-1400s until you change up something drastically through private tutoring or something like that.