If anyone has had this problem or found a solution, any help would be appreciated.
I've been using W3TC and it's been amazing, but for the past month or two, I've been having some really odd issues.
When I upload a new image through the native WP media uploader, a problem occurs with W3TC. The image gets uploaded to my server just fine. It also gets uploaded to my S3 Bucket for CloudFront just fine too.
I know this is true, because when I upload a brand new file with a new filename, it appears on my site example.com/.../image.jpg and the static.example.com/.../image.jpg (from amazon) also works.
Unfortunately, despite the successful upload, the item immediately appears in the Unsuccessful File Transfer Queue. The media links in the article aren't re-written from example.com to static.example.com either.
However, links to older media appears just fine. Clearing the queue, clearing caches, and repeating that process each time fixes the issue with the newest articles.
P.S. I've completely removed W3TC and reinstalled it. Even used the reset settings feature and started from scratch to debug. Didn't help.