You do need a documented positive Covid test before seeking the recovery letter--which means doing a proctored test at home or a test out somewhere (PCR/antigen, etc) so that you have a document listing the type of test, date of test, patient's name and birthdate,and test results. The exemption letter needs to be signed by a medical professional, list the medical practice's name/address/phone#, have patient name/birthdate. State that the patient had a positive test on day x, and is now recovered and cleared for travel. The recovery letter and 11-90 day positive Covid test means that person doesn't need to test before boarding. (This is due to the possibility of having a false positive test result from recently having Covid.)
We recently did this for DD22 who tested positive for Covid at the start of senior week. Since she did the test at the college health center I asked her to get a copy of her results and ask for a recovery letter from them. Once safe passage inspected her docs, the site listed her as clear to sail, no testing needed.