How to lose files

  1. Optimize storage on iCloud - bonus points if you select Desktop and Documents in preferences
  2. Move some files out of the Documents folder
  3. Turn off optimization

To be honest, this is just my guesstimate as to how I managed to lose a lot of some documents. While I am unsure as to the exact steps that caused this dilemma, the fact is I now have problems. One example:

In finder, files are there - they have .jpg extensions, but finder shows them as Kind > CSV Document - this is my first clue something is off. I try previewing or opening these files with multiple apps. Nothing happens at all. I go into terminal - there are no files here. I use ls -la and I see the files are actually in this format: .filename-here.extension.icloud - so they are icloud pointers or symlinks, whatever you call them. But finder gives me no indication of this, so I happily moved the files around, not realizing that they weren’t actually on my hard drive.

To make matters worse, if I go into finder and search for “.icloud” files, I come up with 109 files, all in one particular folder. None of the files I am seeing in terminal are included in this search result. So it’s definitely more than 109, but I’ll have to use some terminal-fu find command in order to be sure…

OK, using find it appears that maybe it’s only 154 files. Not all of those are important, and the ones that are might have a copy somewhere else. Maybe.

Still. given the fact that my entire working career was in I.T. (i.e., I’m not technically illiterate) it seems to me that Apple has set this up in a way that makes it way too easy for someone to lose files. I know that I personally will never use iCloud outside of some basic metadata backup/sync that iOS uses.

I think this switch should never be on. Either you have enough internal storage to have all your iCloud documents locally and available all the time (because Apple doesn’t allow you to move that folder elsewhere, dammit) or you don’t use iCloud Drive ever.


I’ve learned to view and work with Cloud as a separate storage location, not as a copy of my local storage.

When I really must create a copy of something locally to put in iCloud, I use an action in the app called DropZone to COPY TO the iCloud folder rather than dragging + dropping to the iCloud folder. An example is the workflow that I take for PDF editing. I have a DropZone folder that COPIES TO a location in the iCloud storage folder for PDFExpert.

And symbolic links don’t work to reference local files into the iCloud storage location (but they do work to reference iCloud files into local locations).


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