InmateAid works with every correctional facility in the United States including Tallahassee CRC, and your boyfriend does not need to do anything in advance to receive what you send.
Here is exactly how it works. When you write a letter through InmateAid, it is not delivered as an email to your boyfriend. The letter gets printed on paper by InmateAid's processing facility and mailed through the US Postal Service to the prison just like any other piece of physical mail. Your boyfriend receives a real printed letter in an envelope at mail call, handed to him by staff after the mailroom has inspected it. He holds it, reads it, and can keep it.
There is nothing for him to check online, no account for him to log into, and no technology required on his end. He simply gets mail the same way he gets any other letter, except the return address on the envelope is InmateAid's Florida address rather than your personal address.
The InmateAid logo on the envelope is recognized at facilities across the country. Inmates know what it means when that envelope arrives and it is a welcome sight at mail call.
InmateAid has been operating since April 2012 and serves over one million people every month. The delivery process is reliable, consistent, and requires nothing from your inmate to receive. Write your letter, upload any photos you want to include, and it goes out the same day if ordered before 5pm Eastern time.