D. Hoffmann Said:
"My whole problem is that I would like to update this cycle:"
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Copying "External Hard Drive Files" to iCloud Drive:
You can't. However, you can easily do so the opposite round: Use my user tip: Getting a Quick and Direct "iCloud Drive-to-External Hard Drive" Download - User Tip. So, Select All and transfer it over, rather than doing it piece at a time. I would also emphasize that you keep your hard drive and computer on laptop coolers while performing this.
Recommend it Comes Back:
Do your Part: Inform Apple of your feedback of this issue. Include how you’ve troubleshot this, and your results. Apple wont get back to you directly, but the more feedback they receive from its users, the more likely they will know what suits their customer prefer, and what to include in macOS versions to come.
- Go Here: Feedback - macOS - Apple
- Select: "Feature Request" for the "Applications/Utilities"
- Select: "User Interface" for the "Feedback Area"
- Comment: that you want this option and why. Include the URL of this thread.
- Proceed from there as necessary