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How to force a default transform on existing content within a Redactor field

You'll need the Retcon plugin to do this. https://plugins.craftcms.com/retcon
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Transformed JPGs have larger file size than original

The upscaleImages setting only cares about image resolution (pixel dimensions), not file size. If you set this to false, Craft will never create an image with larger dimensions than the base image. So ...
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