Question: This is a pretty silly question, but I can't find an answer anywhere. Is it necessary to send my scores to the colleges on my list each time I register for the SAT? Will registering for a future SAT automatically send those scores--once available--to the colleges that already received my results?
Your question isn't silly at all. The whole SAT registration and follow-up process is, in fact, pretty confusing, and your concern is a very logical one.
Here's how score reporting works: Each time you take the SAT I or II, your scores will be sent to the colleges and/or scholarship services you indicated on the registration form at the time you signed up to take that test. They will also go to any additional colleges or scholarship services you have requested after you registered. These schools will receive the scores for that particular administration along with scores from all SAT I and SAT II you have completed in the past.
However, let's say you took your SAT I as a junior and had your scores sent to Stanford, Swarthmore, Skidmore, and Smith. Then, when you registered to take the tests as a senior, you indicated you wanted scores sent to Harvard, Hamilton, Haverford, and Harvey Mudd. Those four colleges will see your junior and senior scores. However, the folks at Stanford, Swarthmore, Skidmore, and Smith will only have your junior scores unless you order extra reports (for $7 each).
Next time you're confused, think this way: If the College Board sees a glimmer of opportunity to separate you from more of your money, they probably will.