The piece of text I’ve used as this article’s title should be familiar to all WordPress users. Can’t place it? The image above should give you a clue… it’s on the Media Settings page in the WordPress admin console.
I’m going to make a bold statement here:
You should ALWAYS keep it ticked.
Now I’ll tell you why.
If you ever need to copy your WordPress site from one hosting company to another, you’ll probably end up using FTP to transfer the files, firstly down to your local computer from the old host, and then up to the new host. What if I told you that many FTP servers refuse to behave properly when there are more than 10,000 files in a folder? The limit can vary from host to host, but there’s usually a limit of some kind in place. And after the limit is exceeded, on any folders with more files than the limit, your FTP program will not be listing all the files in those folders – and that means you can’t copy all of your files.
“But I’ll never hit that limit!” I hear you say. Well, maybe not quickly, but consider another point. Every time you upload an image into the WordPress Media Library, WordPress makes up to 3 copies of it, often more if you have certain plugins running. On a site that uses WooCommerce, you’ll usually find that at least 6 extra images of various sizes are being created whenever you upload an image. A quick calculation tells us that if you upload 1428 images into a WooCommerce website (not hard if there are a lot of products), your uploads folder will contain over 10,000 files.
UNLESS of course, you ticked that nice little box on your media settings page that says “Organize my uploads into month- and year-based folders”. With that box ticked, as long as you don’t upload your 1400-odd images all in the same month, it will be much harder to hit the limit because as each month goes by, WordPress creates a new folder for the uploads of that month.
So by keeping this setting enabled, you are making it much less likely that you’ll have problems in future if you need to move or copy your site. After all, when you create a new site, who knows how big it might get? Think big and plan accordingly.