files with .icloud extensions not opening

[slaxton]

After upgrading to Mac Catalina OS, I found 408+ of my files in dropbox now have .icloud extensions and won't open. Apple says it is dropbox's issue. I need the files. How do I retrieve them from dropbox?

[Jay]

Hi @slaxton, thanks for joining the Community!

I'm sorry to hear about this. It sounds like the file that you're referring to seems to be a file generated by iCloud.

It's possible that iCloud generated a placeholder of the original file when you moved it to iCloud originally. If this was the case, the placeholder file could have been created prior to you adding it to the Dropbox folder, in which case you copied over the iCloud placeholder instead of the original file.

Please note that this behavior is an implementation that Apple made on iCloud since Sierra.

I'd recommend trying to download your files to your machine from iCloud using their system, and then move them to your Dropbox folder.

Hope this helps to clarify matters!

[slaxton]

Hi Jay,

Thanks for this. In fact, I never moved these files out of Dropbox - they were safely in Dropbox when I had Apple clean-install Catalina. Somehow during the installation, Catalina added .icloud extensions to aliases already in Dropbox. I don't understand how the OS got access to them - that seems very wrong to me - but I know that they are aliases because when I couldn't open the files directly from dropbox, I dragged one to my desktop and it disappeared, "poof!" Apple thinks that the files are actually still in the Dropbox cloud, I just can't access them because they have .icloud extensions preventing them from linking up to Dropbox. They say the only way I can access the actual files (as opposed to just the aliases) is through you, Dropbox. Can you help?

Thanks,

Susan 

[Jay]

You can try downloading each file and folder manually via the Dropbox site to your computer, however, it does seem like iCloud has made these changes, so it might persist even after putting files back into the Dropbox folder.

Is there no option with iCloud to download the files from their system, or to disable that feature?

[slaxton]

Hi Jay, 

Thanks for being in touch. When I try downloading the files from Dropbox, they completely disappear - it is clear that the "files" with iCloud extensions appended are merely aliases.  I was on the phone with Apple yesterday for 2 1/2 hours and they couldn't find a way to fix the problem, though they acknowledged that the Catalina  conversion probably caused the issue, as indicated by the "iCloud" appendage. Note that this is a double extension; the files in question read "filename.docx.icloud" etc. 

Apple says my only hope for retrieving the 408 affected files is to find out from Dropbox another way to access the actual files rather than simply the links to them. They can't do that for me, so I am wondering if Dropbox can. Note that of course the computer was backed up by Time Machine, but Time Machine (understandably) doesn't back up Dropbox files, only the software. I thought the files in Dropbox were "safe" from the clean reinstall of Catalina, and as it turns out, they were not. How did Dropbox let Apple into their system? I'd be worried about that if I were Dropbox.  

If you can't help me, can you direct me to someone who can? If I subscribe to a higher level of Dropbox, can I speak to someone on the phone for support? 

Thank you,

Susan

[slaxton]

Hi Jay, 

Thanks again for trying to help me. The Apple technicians say that there is no way to change or reverse the extension on the file that will make it so that I can retrieve the files themselves. Yes. It appears that iCloud went into Dropbox and replaced the Dropbox links with aliases, but they still say that the actual files are in the Dropbox cloud and not in the iCloud. So what I am asking you is where then are my actual Dropbox files now, and is there some way Dropbox can make them available to me? By the way, what I've discovered by rummaging the internet and iCloud is that these are called "icloud synchronization files," if that is any help. 

Thanks,

Susan

[Jay]

You can try and see if the files were deleted so you can recover them.

Otherwise, try checking the version history on one of the .icloud files to see if the full file is in the history.

[slaxton]

I've tried both delete/restore and versions. None of the files are in the "deleted" folder. When I drag them off Dropbox to my desktop, they disappear from the desktop, but appear in the Dropbox deleted area. When I "restore" them to Dropbox, they still have the .iCloud extension and won't open.

There are no other "versions" for these files.

If it's any help, they're identified in my Mac finder as "iCloud extension files," not pdf, docx or jpg.

Where exactly does Dropbox keep the actual files (not the mere links to them)? How can I access them? Are they lost forever? If I upgrade to another level of Dropbox, can I get telephone support? 

Thanks,

Susan 

[Jay]

It sounds like the files are no longer on the Dropbox site, if you're not seeing any version history, or deleted files. This would mean that the files are no longer on your Dropbox account to be able to recover them.

When did you upgrade to Catalina? Was it within the last 30 days?

Regarding phone support, this is only available on Dropbox Business teams, which requires a minimum purchase of 3 licenses.

[slaxton]

Hi Jay,

I upgraded to Catalina on August 23. The computer kept crashing afterward, so I had to send it to Apple for a clean install. That took 10 days. Everything was backed up on Time Machine before the upgrade except, of course, the files that were in Dropbox. I didn't realize what had happened until I tried to open one of the affected Dropbox files two weeks ago, and I have been trying to figure it out ever since. Apple says they can't help me with dropbox files–they claim they don't know your system. I've spent hours on the phone with them.

If Dropbox no longer has the files, that is very bad news indeed. Did iCloud take the files out of Dropbox? How could Dropbox have allowed that to happen? I thought they were safely stored there, away from the upgrade, and didn't have to be backed up.

-Susan