Regenerating not always deletes old size thumbnails
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My featured images usually are 2060×687 pixels.
For testing purposes, I changed the size for ‘large’ to max 2060 wide and max 300 high. After regenerating the thumbnails, on my site indeed a thumbnail of 899×300 had been used.
So I set the size back to max 2060 wide and 2060 high, regenerated the thumbnails again (on the simple image size admin page), but on my site the old images (899×300) still had been used. Even after clearing cache, refreshing browser, etc.
Then I decided to regenerate the thumbnails through the option in the media library (I tested regenerating a single image, as well as bulk regenerating all images), and after that, the images used on my site suddenly were the righ size (2060×687).
So, it seems regenerating through the simple image size admin page does not delete old thumbnails, while regenerating through the media library page does.
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