My rent auto-pay failed on the 1st and the late fee was $95

Heads up for anyone renting in a big city: my payment app showed "scheduled" on the 1st but the landlord's portal says it never landed, so I got hit with a $95 late fee on a $1,650 unit in Chicago. Turns out my debit card expired in March and the app just quietly stopped trying after one failed try. Nobody emailed me, nobody called, the balance just sat there looking fine. I called the office, showed them the app screen, and got $50 knocked off, but only because I asked on day two instead of waiting a week. Now I send rent as a manual transfer on the 28th and keep a screenshot. Has anyone actually gotten a full late fee reversed, or is half off the best you can hope for?