The most recent time this happened was March of this year, with Chile's Aysén Region dropping DST and moving to the newly created America/Coyhaique.
https://data.iana.org/time-zones/tzdb/NEWS
I used to manage a large application for scheduling shifts at warehouses in many different locations, and storing future events as local timestamps and lazily converting them just before calculations into their location’s zoned time was the only way I could stay sane.