jpegoptim
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--auto-mode can result in an infinite loop
Generally this seems to be possible with any JPEG file after repeatedly running
jpegoptim -v -m 80 --auto-mode file.jpg
Image quality limit set to: 80
Using maximum of 1 parallel threads
file.jpg 658x881 24bit N Exif,JFIF,ICC [OK] (retry w/progressive) 153443 --> 106748 bytes (30.43%), optimized.
jpegoptim -v -m 80 --auto-mode file.jpg
Image quality limit set to: 80
Using maximum of 1 parallel threads
file.jpg 658x881 24bit P JFIF,Exif,ICC [OK] (retry w/normal) (revert to progressive) (retry w/lossless) (retry w/normal) (revert to progressive) (retry w/lossless) (retry w/normal) (revert to progressive) # repeat forever