When can a D1 school officially begin recruiting and/or offer a HS prospect (What year in HS would the prospect have to be)?

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Regarding your question posted, here is the timeline for "official" recruiting:

* Sept. 1 of player's junior year - colleges can begin sending letters

* July 1 following players' junior year - colleges can begin making weekly calls

"Unofficially," recruiting and offers can occur way earlier and in many forms:

* A college can recruit a player when he is on campus for an unofficial visit, at a game on campus, or at a camp/showcase

* At any time during a player's high school years, a college can call the player's coach or select director and have them ask the player to call the college. If the player initiates the call, the college can recruit and make an offer.

* I believe NCAA rules still allow a college college to email players at any time -- not just after Sept. 1 of junior year.

I hope this answers your questions.