I am having the exact issue described here:
There are many random images that are not transferred to S3 when using the Upload feature in W3 Total Cache. I have checked the Unsuccessful file transfer queue and it is always empty.
These images are in the exact same folders as the images that are successfully transferred. I have deleted all files from S3 and done the upload from W3 Total Cache again with the exact same results. Permissions are the same on all files.
Here's an example of one that doesn't upload...
/wp-content/uploads/2012/07/Crossfit-Girls-420x315.jpg
and one that does upload:
/wp-content/uploads/2012/07/Crossfit-Girls-300x300.jpg
Any help? Thanks.