This may just be a minor limitation of the device being accurately reproduced in the SImulator but... FWIW... the US changed from Standard to Daylight time last night, and although the Playdate Simulator was set to Automatic time, it did not reflect the time change untll Automatic was toggled on/off.
(I had it asleep at the official moment of the changeover, but the next day I had it running a while and saw no automatic change.)
Just ran into this: Australia changed off daylight saving last night, and my Playdate which was set to "automatic" time, didn't adjust until I flipped it to manual and then back to automatic, causing it to reload the time.