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I have a few music files I put on iCloud Drive a while ago, and now I want to move them to my Dropbox directory.

So I tried to download them locally in order to move to my Dropbox directory, but the download won't start by double-tapping the filename.

I also tried to choose the "Download now" section on the file (maybe the English description is different, but it is the third menu item on the pane) but the download won't start, either.

In the past the download started immediately, but now it won't. There is enough storage in my local computer (about 90GB at least). Restarting the computer won't resolve the problem.

What is wrong with it and how can I download the files? I use Catalina Beta 6 on my 2017 12' MacBook.

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  • It might be a Catalina Beta issue...
    – Steve Chambers
    Commented Aug 23, 2019 at 11:42
  • It's a beta, it's buggy, don't use it on a machine that you wouldn't want all of the data to be wiped from.
    – At0micMutex
    Commented Aug 23, 2019 at 13:25
  • It's not Beta. It happens on my released version of Big Sur.
    – Lance Kind
    Commented Nov 8, 2021 at 2:23
  • The weird thing is that "download now" works correctly for the "standard" iCloud drive folders. I'm seeing the problem with files in the root directory of iCloud.
    – Lance Kind
    Commented Nov 8, 2021 at 2:24

2 Answers 2

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Apple lets you click the file in Finder to download, but I prefer using a utility specifically designed for this.

Bailiff lets you set up rules and evict files the default settings think should be stored locally as well as request a download / pin files you want to keep whether the code thinks it should be freed up and only exist in the cloud.

Cirrus lets you look at the logs (and there are tons) so you can examine any specific file or container if needed to sort out a pause or error if those are to blame. They should work on beta versions and the developer is very responsive if you have a suggestion or need support in my experience.

I'm very happy with the default behaviors, but I get some people want to dictate and not trust the files come and go or wait for a download based on your internet connectivity and speeds.

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Sure fire workaround: Go to iCloud.com, login, open the drive, and download the content from there.

Other tips that I didn't try that entail toggling iCloud sync: https://windowsreport.com/mac/icloud-not-downloading-mac/

As to why "download now" doesn't work or clicking on the files on the finder doesn't trigger download, I don't know.

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