iCloud Files refusing to upload
Thankfully, there’s an app to figure out exactly which files are uploading, which are set and which are failing / out of date with iCLoud.

Even better, it’s well described and actively being developed and I believe, free to use.


https://eclecticlightdotcom.files.wordpress.com/2018/06/cirrus11.zip


The general release blog post is:


https://eclecticlight.co/2018/05/19/cirrus-version-1-0-release-the-icloud-tool-is-ready-for-general-use/


Keep in mind that there are throttles to pause uploads after so many GB a day so your initial ingest might take a while if you just dumped a ton of data and are not leaving your Mac on and not sleeping overnight or over a period of several days. I would consider reducing the initial upload to 3 GB or so and let that catch up if you can at this point.