How can I make OSX to upload files to icloud? As you can see from the screenshot, some of the files have the 'download from icloud' icon to the right of the file name, but some of them (from DSCF6758.RAF onwards) are not.



The folder is on the iCloud Drive.

I still have plenty of space in the iCloud.

At the moment my SSD drive is low on free space (only 5% free space left)



How can I trigger the upload process on these not-yet-uploaded files?
The menubar app Bailiff lets your pin files on your drive and evict them without needing to wait for the background processes to do the work for you. 


https://eclecticlight.co/cirrus-bailiff/


Once you’ve got the files removed, you still need to wait for snapshots to purge. The df command isn’t going to show you purgeable content, so this tool. It might not be sufficient to fix what you’re trying to do in the end, but it does do what you asked.