Uploaded Images Go Into Old Year and Month Folders Inside Upload

It might be that you’re uploading the images to posts or pages that were previously published, and the images are being placed into the folder corresponding to the year/month when those posts/pages were originally published rather than the most recent image folders.

This post shows that, if you’ve checked the box to “Organize my uploads into month- and year-based folders,” what I’ve described above will happen:

https://jackiedelia.com/how-wordpress-handles-media-files-uploaded-to-old-pages/

Thanks Jamie. However, these images are going into new pages that are in draft mode, so I don’t think that is causing the problem.

As an example, here is a page I recently published (all images show they are in folders from 2012)
https://spfinsurance.com/how-much-life-insurance-do-i-need/

Here’s a page published before the problem started (all images in correct upload folder)
https://spfinsurance.com/2017/02/life-insurance-for-an-uncertain-world/

Tim

I set up a fresh install with the latest copy of WordPress (4.8.1) and installed the theme unit test data: https://codex.www.ads-software.com/Theme_Unit_Test. When I uploaded an image to the media library, it went into the uploads folder for the current month/year. When I uploaded an image to a post published several years ago, it went into the uploads folder corresponding to the month/year that the post was published. So it seems that, with the latest WP version in a clean install, the media uploads are being handled as expected.