This is apparently a common problem for the Sony Bravia’s and JPEG support isn’t the best. A little research has found a few pages referencing the spec DCF2.0/EXIF2.1, but what does that really mean?
Apparently it’s a limitation when using JPEGs of a high quality with Chroma Subsampling 4:4:4. I had read elsewhere that images needed to use sampling 4:2:2 or 4:2:0 but I was having varying problems trying to convert what I had using GIMP. Either it (or I) wasn’t up to the challenge.
In the end I found ImageMagick’s “mogrify” the solution to my problems.
I’m running OSX El Capitan. I used MacPorts to install:
sudo port install ImageMagick
After a few minutes installation it is as simple as running “mogrify” over the images:
mogrify -sampling-factor 2x1 /Volumes/USBKEY/*.jpg
I found my solution thanks to Wouter of Belgium who had the same problem saving files from Adobe’s Lightroom 2. He has Homebrew installation instructions on his site if you’d like to pay him a visit.