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If I'm reading it right, your regex has only two items in (), which means that only $1 and $2 have any meaning. I copied your sample text and went to https://regex101.com/ (note: this is not an endorsement) to try to assemble a regex that'll cover all your images. Here's what I ended up with: Pattern: ^(.*\/[0-9]{1,4}\/[0-9]{1,2}\/)([^\.]+)\.(jpg|jpeg|gif|...


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Where am I going wrong? Actually, your code is just fine. Except that I would simply use wp_generate_password() to generate the random string. :) WordPress will still think that the scaled version is called painting-scaled.jpg , etc. Resulting in broken images. Yes, that's correct. Images are stored as posts of the attachment type in the WordPress posts ...


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Upon debugging we found the wp_max_upload_size function was returning 1MB. The u_bytes and p_bytes were as expected and equal to 100MB as defined in our uploads.ini file but the application of upload_size_limit filter changed the size to 1MB i.e., the problem was at: return apply_filters( 'upload_size_limit', min( $u_bytes, $p_bytes ), $u_bytes, $p_bytes ); ...


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The answer @robbert is a great, great answer. However, it's a little dated (I'm using WordPress 5.7) and I wanted to do this exact same thing, so here's a slightly updated answer with a few extras: I've used the slug size rather than the dimensions because this is a little cleaner and wanted to demonstrate it from the @robbert code. An extra filter for ...


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