How Do I Know If A File Has Been Successfully Synced To iCloud Drive?

OS X 10.10.2 now has graphical upload progress bars:

When things get stuck, or you have a slower upload, there is a brctl tool that ships with Yosemite to monitor changes in all iCloud backed documents. Open terminal and type the following command:

brctl log --wait --shorten

On macOS Catalina 10.15 use the following command:

brctl log -w --shorten

It will show you a brief summary of the sync changes both up and down. The wait causes it to run continuously until you close the window or issue Control+C to quit brctl process. If you are familiar with the grep command line tool, you could filter the results to just show upload progress, but most iCloud accounts are quite low volume in terms of changes, so your upload of many files will likely dominate the results.

https://www.icloud.com/#iclouddrive

Also, the empirical way to tell if a file is synced is to log in to iCloud drive on the web interface and verify a file and/or folder is up there in the clouds.

This was such a problem for me I actually made a utility called "iCloudStatus" which basically behaves the way Dropbox does by showing a status icon in the menu bar (see below).

The other alternative is looking at the Finder but if you're uploading large batches of documents nested deeply in folders like I am then it will be a time consuming experience knowing when your files are uploaded.

You can download it here and for full disclosure I am the developer.

I have noticed the same problem. The only way I have found is to look at the upload status bar in finder, way down at individual file list level. It shows how far the file has uploaded and then changes to file size when completed. Definitely not as helpful as Dropbox.