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My roommate has a PS4 with PS+ and downloaded Bloodborne, we have different users, and I play the game on my user but I want to buy the DLC, if I buy it will it work on my user with a different PSN account that has no PS+?
Or do I need to buy it and download on my friend's user and account?
If I buy on his account will I be able to play on my user? Sorry if this got a little bit confusing.
It is possible to buy DLC without owning a base game. I cannot find any official documentation regarding it, but I found this Reddit thread and tried myself to add DLC to shopping cart in store. So you can buy it on your own account.
Both of you will be able to play DLC - this is how sharing works for local accounts. However, if your roommate will ever decide to stop paying for PS+ you will lose access to game itself.
If you purchase DLC on his account everything will be the same - both of you will have access to game and DLC until PS+ is active.
