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(+1)
upload a build and mark it as a Windows build, but the game isn't tagged as an HTML5 AND Windows game, just HTML5

You sure you ticked the box on the downloadable executeable file that shows the platform? Because that should totally work.

https://itch.io/games/platform-web/platform-windows

(There are no buttons to generate this url, since selecting one platform changes the platform selector, but you do can combine those.)

Yeah I did? It still didn't work. And now it did. Why does that always happen to me?

Well, thanks for telling me anyway! I'll keep an eye on that!