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If anyone knows a good solution for this that would be amazing, but I suspect it's a lost cause. Accudio/1290240131341774848
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Managed to come up with a system for my specific circumstance. Using a server side logic using the aspect ratio to work out when the image will be 100% width or height. We then combine with the standard media queries and inline the calculated widths into the sizes attribute.
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It's a nasty hack, but it works. It's very specific to the circumstance so I won't post any code, but if anyone needs some help implementing something like this let me know.