What should I do if my CMS keeps re-uploading oversized images?

If your CMS keeps re-uploading oversized images, the fix usually depends on where the resizing is failing. Here’s a practical checklist:

1) Confirm where the image is being made “oversized”

• Before upload: the file itself is too large/dimensions too big.
• During upload: the CMS accepts it, but stores the original instead of a resized version.
• After upload: the CMS generates a resized version, but the front end is still serving the original.

2) Check CMS image settings

Look for settings like:

• maximum upload dimensions
• automatic image compression
• thumbnail/medium/large size generation
• “preserve original image”
• CDN or media library optimization options

3) Make sure the frontend is using the resized version

Sometimes the CMS generates smaller images, but the page template still references the original file.
Check:

• image size being requested in HTML/CSS
• responsive image attributes (srcset, sizes)
• template logic or component settings

4) Rebuild or regenerate thumbnails

If image sizes were changed after images were already uploaded, existing files may not have been regenerated.

• Run a thumbnail/media regeneration tool if your CMS has one.
• Clear caches after regenerating.

5) Inspect plugins or middleware

A plugin or integration may be:

• re-uploading the original file
• bypassing optimization
• syncing from another system and overriding resized images

Disable them temporarily to test.

6) Check server-side image processing

If the CMS relies on server libraries to resize images, make sure they’re working:

• ImageMagick / GD / libvips installed correctly
• PHP/Python/Node image libraries functioning
• memory limits not too low
• permissions allow writing generated files

7) Add upload restrictions

To prevent oversized uploads in the future:

• enforce max file size
• limit pixel dimensions
• auto-compress on upload
• reject images above a threshold

8) Clear cache/CDN

If a CDN or page cache is serving the old large image:

• purge CDN cache
• clear application cache
• hard refresh and test again

9) Test with one known image

Try a controlled test:

• upload a large image
• note the original size
• check the stored file size
• inspect the page source to see which file is used This helps pinpoint whether the issue is upload, storage, or display.

If you tell me which CMS you’re using (WordPress, Drupal, Contentful, Strapi, Shopify, etc.) and whether the oversized image is happening on upload or on the page, I can give you exact steps.