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So one of the schools I applied to (USC) requires a dean's letter for academic honor code violations. I was sanctioned my freshman year for getting too many lockout fees, which was against my undergraduate school's honor code. I decided to report and and requested a letter from my university and it's been a few weeks. I asked them to resend, and the letter still hasn't been received.
Just wanted to know if anyone has had experience with this or if academia just operates on snail mail

I went in-person to my registrar. She's a very kind and intelligent woman and drafted a letter within a few days of me asking. She sent me the draft and asked if it looked OK, and when I confirmed she sent hard copies out to the schools that required them.

Email the admissions office (if you haven't already). Sometimes they have received it, but it just doesn't reflect as such on the status checker.

I had one sent to USC. I emailed them about a week after my UG sent it to confirm receipt.