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What are best practices to storing uploads in WordPress?

We’ve been storing all of our images using the default /year/month/day, but I’m thinking there has to be a better way to store things because everytime that I update a image or pdf. I have to reupload it and it gets stored in a new location.

We occasionally get in the situation where we update a pdf that was uploaded one month, external users are linking to that one and when we reupload, it’s stored in a new location instead of it being overwritten.

So to make sure that people that are linking to the correct PDF, I have to either find the original upload folder and upload through FTP or put in a redirect for the older version.

I know you can change the upload location to store in one folder, but I can see that getting out of hand.

What are best practice for storing files? I haven’t been able to find a plugin that allows you to store files based on post type or choose upload location.

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What are best practices to storing uploads in WordPress?

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