Dropbox to Icloud

I’d like to go from dropbox to Icloud.
But the organization of Icloud does not seem simple to me.
Is it better to use the different Page, Numbers and Keynote folders, and create folders within the different domains (and thus create several times, for example, the folder of each client with a Page file and a Numbers file) or create, like Dorpbox, a “document” folder where will be merged the Page and Numbrers files of each client?

I made the switch and keep everything in the Documents folder. Shared with the Mac and iOS.

I actually do both ways of organization. If the files are one offs and I’m probably only going to be accessing them in those apps, then I let them live in their respective app folder.

If the files belong to a group, like a project then I will put them all in the same folder. That way if I need to open the keynote and numbers file at the same time, then I just open the finder window to their folder and open both files from there.

For example, the training I give I present from keynote. There are no other files that go along with the presentation so that just lives in the keynote folder. Now I have my expense reports for work, but because it has a numbers file and a PDF that goes along with them, I keep the files inside 1 folder.


I would really like to know how @MacSparky organizes his iCloud Drive. I would love to ditch Dropbox and go full iCloud but

  1. I am scared to delete those default Application-Focused folders (Pages, Day One, etc) because I don’t want to break things.
  2. I have more content that could fit in iCloud and that I want to move there, but I don’t want all of it syncing back to my Mac.

I think there is a way to optimize Mac storage for this scenario?

Love some insight.


I’m having the same thoughts about moving from Dropbox to iCloud. With the Files app on the iPad documents are so much easier to work with. And moving to one cloud service seems like it would reduce the risk of data hack. I waffle on this idea though as do I want “all my eggs in one basket”. :slight_smile:

I was thinking that I would go more of the client/project route as far as structure. I believe early on when iCloud was primarily a way to sync between devices, and wasn’t as visible to the user, the application folder structure made sense. I seem to remember seeing developer notes for some apps that indicate certain folders should not be deleted because they were hard coded in the app.

I probably won’t start off by deleting anything and will just add the client/project folders and move working documents around within them as needed.

Once selective sync is available on iCloud, I plan to go all in. As it stands, I have too much data in Dropbox and not enough confidence in iCloud to manage which files it stores locally.

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I really like iCloud Files but I find it really difficult to use for some reason. Probably user error on my end by every time I search for something in Files it never shows up. Search in Dropbox and finds it every time. I really dislike the array of misc. app centric directories created in Files - can you delete those?

I made the move about a year ago. I have more files in iCloud then will fit on my MacBook Pro and I just let the Mac ‘optimize that by itself.

I have found that my active files are local and things I haven’t touched get ‘optimized’. I pay for the 2 TB plan and I have more then enough room.

Files app: saving grace really. I love having access to my desktop folder from all my iOS devices. Simple things like saving a file that I want to do something later with on my laptop.

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Ever since iOS 11 and the indispensable FILES app, I’ve been ALL IN with iCloud and the iCloud Drive. As a 12-year Mac user with thousands of content documents of various types in my “Documents” folder hierarchy, I organize all of my files for all Apple devices under the Documents folder in iCloud. I have had no mishaps or losses with iCloud. I pay for the 200 GB storage level in order to make all documents and photos accessible to all my Apple Mac and iOS devices.

I highly recommend deleting the various app-specific folders. They are a holdover from the old iOS days prior to iOS 11 and prior to the Files app. No mishaps whatsoever after deleting app-specific folders.

I continue to use a free (2 GB) account at Dropbox solely for one set of several hundred document files — namely, those that I want to share as a file archive with my wife. Apple is now stepping toward collaboration and multi-user (and family) file sharing in iCloud, but IMHO iCloud sharing of large multi-folder collections of hundreds of files is not yet as simple as sharing in Dropbox.

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I’m also all in. I haven’t bothered to delete the app-centric folders. They just stay there, and I ignore them. There are some iOS apps that don’t do iCloud other than the old way (GoodReader for example), but generally I get to keep my many decades old hierarchical file system, available from all my devices.

What I miss from Dropbox is the ability to share a URL to a file easily or to collaborate on a folder full of stuff. Dropbox nails this, and iCloud doesn’t touch it at all. Plus, Dropbox has a backup system built in—I think iCloud should be able to match all these features.

I am really thinking to move from dropbox too… I find that dropbox does not play so well with the Files app: Favorite folders disappearing from the side bar, the files displayed are not always in perfect sync,…
Apart from the inability to share a folder like dropbox, it seems that iCloud will fit the bill for me.