hi are you getting any error messages? Unzip the folder and there is an upload option on the playdate website .. let me know any more info thanks!
Viewing post in Dove & War Playdate Visual Novel comments
Hey, new to playdate as well, had mine for a week, I'd like to recommend contacting playdate as the past 48 hours there have been issues purchasing and sideloading titles. I've sent in customer support tickets. I originally had Tochi sideloaded on mine and it was fine but I was figuring everything out and deleted the file. Now I can't sideload some of my other files. I'll try to sideload on my end and give an update. It may not be your game it may very well be issues on Playdates end.
I don't really know. I've only had the OS 2 version, as my Playdate only arrived a week ago. So it had to have been some time ago. If the game was working fine before then, thin I'd disregard my comment. However you should contact playdate (panic) as this is apparently affecting several games at this time. Specifically ones on itch.io
Edit: by "this" I mean, where games in pulp were working fine and then suddenly they no longer can be added via the sideload option. I'm not really sure what the issue is but it is doing this for 5 other games that I had side loaded previously on day one. The files have not changed. So there's no reason they shouldn't be "able to resideload".