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(+2)

I think I found the issue: I raised the price with 99 cents in order to harmonize more with the price level on Steam. This means that you might have to add another 99 cents in order to unlock this content. Sorry for the inconvenience, I wasn't aware of the fact that this would influence people who'd already bought the season.

(+1)

How would i go about adding the 99cents with out having to flat out do another 11 on top?

(+2)

That doesn't work on itch. You can not add money. But I have the game Radiant bought with 5$ and now it costs 10$ and I haven't lost it.  

It should work now, after I restored the price to the original level. Let me know if there are further challenges.

Yes, it is working, I've just reinstalled from itch.io app

Happy to hear.