I'm working a big batch of files destined for an e-commerce website. I'm outputting them as JPEGs, 1200px x 1200px. I've been asked to keep them around 250KB, and exporting the JPEGs using the Image processor, JPEG quality 5 hits that target. However, I'd like to know if there are any technical reasons why doing it that way is inferior to adding the extra workflow step of sending the high quality JPEGs through a compression tool, like this one: https://compressimage.toolur.com/
No point. Jpeg compression is jpeg compression. The general rule is to do it only once if you want to avoid artifact buildup.
In fact, recompressing will most likely produce a bigger file than saving at a lower quality level to begin with. The jpeg algorithm works much more efficiently on flat areas than it does on busy high frequency detail. The artifacts from the first compression will be treated as added detail in the second round.
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