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I have an Xbox Serires S and a bunch of old physical discs games. I now realize those discs make lovely paperweights...

I have some saved data on the cloud and a local external hard drive. If I re-buy the digital version of the game on the Xbox, will the saved data be available when I start the game up? For example, if I have a saved game of Red Dead 2, can I just re-buy the game online and start from my saved game? Or would it make me start a new story entirely?

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According to this answer in the Microsoft Community, your saves will still work, as long as you're signed in to the same account that uploaded the saves to the cloud.

Based on prior experience with multiple other platforms (but not the Series X|S, as I don't own it), I would recommend buying the digital copy from the same region as your physical copy. In some cases (but not all), two copies of the same game but from different regions may not be compatible to one another. The same applies to DLC. If you already own DLC for the game, it may not work with a digital copy of another region.

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