Having to move back to Dropbox

I tried to move from Dropbox to iCloud Drive however I have had multiple issues that Apple cannot seem to fix. Here is my story.

Six months ago, I purchased an iPhone X and my iCloud Drive would not sync. We tried a new iPhone 8 and nothing… same issue. I would create a folder on my MBP and it would sync to my iMac, iPad, even my iPod touch but never on my iPhone X. After 30 email to tcook@apple.com (I know he never saw it) and getting a call from the “Executive office” and another 3 weeks it started to work. I asked them what they did. They said “it just started working”. I explained to them that if they do not identify the problem then there is no way to fix it.

Fast forward 6 months. I started to notice that iCloud Drive was creating up to 110 duplicates of the same file and consuming space of course. They had me delete the files from iCloud and re-sync. I did so, but now its been 3 days and I do not even have the folder structure on iCloud from my MBP. iCloud Drive is so unstable that I cannot continue to use it. Apple still does not have a clue what the problem is. The only options is to escalate to the “engineers” which just send an email saying “everything looks fine and it should be working” but it does not. Dropbox just works. I so wanted to move to iCloud Drive but their lack of understanding of the product and the lack of desire to truly fix it is sadly crystal clear.

Over the past few years I’ve tried Dropbox, Google, Amazon, and iCloud. I too, tried to consolidate on iCloud, and found it stable, but frequently so slow to sync that I found it unusable for the way I work. I have seen it take 30 - 60 minutes to start the sync after I dropped 15 - 20 files into a folder - on a 1G (up&down) circuit.

In the end, I went with Google. Performance is equal to Dropbox and I’m a G Suite user, (preferring Google apps on IOS, and webmail on everything else.) so it is a good fit for me.

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Has anyone gone all in with OneDrive?

I haven’t’ for personal use. (I split between iCloud, Dropbox, and One Drive.) However, when I was teaching school, the school I taught at used Exchange and Office 365 with Windows workstations. I put all my school-related things there to ease “passing out” the files to my students. I didn’t have any issues with it at all. The syncing was fast and stable. It was the best way to go between my teacher-issued Air and my classroom desktop.

I use OneDrive for my work stuff since it comes with 365, but it’s not great for sharing. Once you experience sharing with Dropbox or Google, it’s hard to get too excited about OneDrive.


Half the time my students had issues trying to get their files shared with me. I thought it was user error since many hadn’t used it before. However with your statement makes me think it was OneDrive. Google Drive and Dropbox do spoil a person.

UPDATE: These “engineers” at Apple are incredible. Last time I had this “no sync” issue, they reset my iCloud account and it started to work. Of course I had to re-sync hundred of gigs back to iCloud Drive. I told them that they never identified the problem and because of that, the problem was not “solved”. I used the analogy of the memory leak. Once you reboot the computer, the memory leak symptoms disappear until you hit that memory space again. They wanted to reset my account AGAIN since I am having the problem again.

They were supposed to purge the “recently deleted” files (~40GB) because being on iCloud Drive. The “genius” deleted everything EXCEPT the “recently deleted”.

Long story, shot the reset my account AGAIN even though I told them not to. Now of course everything is working until the next time. This is the second time in a year that I have the same issue.

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Do you use Backup and Sync or Drive File Stream? If yes, how has your experience been compared to the Dropbox app?

How did you go about getting the reset to be done? Phone call? Jumping through several loops/transfered to another department, as usual with a phone call to Apple? I’ve thought about doing this since I constantly get weird sync issues that are hard to replicate or prove on the spot.

Had OneDrive at my previous job. It wasn’t great - IIRC OneDrive - like Creative Cloud - won’t sync files with certain characters in the filename - ? | : etc
Also, I thought it was unintuitive how some files were on our Sharepoint, some on our OneDrive, some on my OneDrive, and getting them to work together or syncing those locations was all too cumbersome coming from using Dropbox or Google.

When iCloud is good,

It is very good indeed,

But when it is bad it is horrid.

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Is it just me?
Am I the only person who has ever had no problems with iCloud?
Or have I just not found the problems yet?
now i’m starting to wonder whether i should move my files…

I use Backup & Sync with a standard Gmail account. (I also have a private domain legacy G Suite account). Sync starts as soon as a change occurs on Google or my local drive, the same as occurs with Dropbox.

I stopped using Dropbox on Mac because of their client software. I occasionally use Dropbox on my iPad if I have no other option.

I use OneDrive for Personal and Work. Not a heavy user, but it works fine for me since I have Windows and Mac and everything seems to worked fine.

Cloud Services Comparison (202007)

I am another user who has tried them all. Here are my insights which might or might not help you. Some of my comments involve the clients, especially on iOS.

I am currently using iCloud and having no problems, and have had no problems for over a year of using them.

My cloud storage is 165K files, and about 200GB.


  • Fast and stable. Not as fast as Dropbox which does much of their syncing over a local LAN
  • Very glad they have implemented a basic selective sync on MacOS. Wish they would do this on iPadOS
  • No in-file search on iOS. Does to in-file search on MacOS


  • I have been running my small business on G Suite for 10+ years. Originally it was very good, but now sucks in a big way
  • When there was just Google Drive the sync was very good. Now that they have 2 different services: Backup & Sync and Filestream, both are horrible.
  • Every time you shut down your computer, upon startup it goes thru the sync process all over again. This can take anywhere from 2-6 hours or more. You can imagine what impact this has when you travel with a laptop.
  • File Management is very poor. You can’t do many mass actions on files that we are so used to on the Mac. When you try to do it in the Finder, many crashes.
  • Google is much, much better if you only use it via a browser. Very fast to search, very slow to browse.
  • Shared drives work well if you need that function
  • Very minimal ways to sort your files when in the browser. And did I mention that using Finder to manage Google Drive will send you to an early grave.
  • Does in-file search


  • Currently have an Office 365 subscription with 1TB of storage
  • Fairly fast & stable. Like Dropbox, they also do a LAN and bit-block sync. (Not sure if I am calling it directly)
  • Multiple occasions where sync just doesn’t work. Typical Microsoft
  • They don’t accept all of the characters in a file name that Apple allows. If you migrate your files, plan on a lot of cleanup
  • Somewhat limited on how many files per folder
  • Does in-file search
  • If I didn’t dislike Excel / Word / Powerpoint so much, I would probably use OneDrive more


  • My original cloud service that worked tremendously well
  • Moved away from due to several reasons: truncated files names on iOS, their attempt at becoming more invasive on my computer
  • Extra cost for something I am already paying 3 other cloud services for.


iCloud is by far my favorite. OneDrive and Dropbox and very similar. Google Drive is terrible.


Quite striking that iCloud seems to be improving over time while others are degrading…

I agree, if I had that many problems with Google Drive I wouldn’t be happy either. When you say File Management is very poor, you are referring to the web interface, correct?

I did my initial upload to Google by syncing files via Backup & Sync and now do 99% of my file management via the Finder or the Drive app on my iPad. So far, I have never experienced any crashes, and I’m primarily an iPad user so I rarely notice the sync process on my Mini.

While I have seen some improvement over the past couple of years I continue to have problems with syncing files & notes on iCloud. Maybe my iCloud files are still on Microsoft Azure servers rather than Google’s. :slightly_frowning_face:

I have also tried a few (Dropbox, iCloud, Google Drive).

Dropbox is extremely reliable and very fast at syncing. It works really well and integrates seamlessly into the Finder. I use the business plan which is expensive but gives unlimited storage and undos of deleted files.

iCloud - I want to like it because it is Apple but it never seems to quite work right. Even syncing contacts and calendars can sometimes be flaky. And although I love everything Apple they are notorious for changing and dropping things as and when they want. I used one of the very first iterations of Apple Cloud syncing - it was called .Mac and I found it not only very unreliable but then Apple suddenly decided they weren’t interested at that point in Cloud syncing and shut it down with a deadline to remove all my files (they then started it up again as iCloud but by then I had lost faith).

I now use iCloud to sync Contacts, Calendars, Notes and PhotoStream and I have paid for more space as my daughter uses it for her school work - but I have yet to trust it as my primary Cloud storage. I will stick with the reliable and fast Dropbox as long as it exists. I just hope they aren’t bought-out by Apple.

Ooh I am not the only one then apparently! I thought I might have been doing something wrong with my system since I noticed this happening to me. I’ve experienced something similar with other apps and I guess in my mind I’ve even put notifications about “You’re opening this app for the first time” that have happened with some non related apps into the same bucket of possibly having some permission issues.

I’ve also kinda tried Creative Cloud because for some reason I have 1TB of storage with them whether I’m subscribed to a plan or not.

CC has the same issue as OneDrive has with not accepting certain characters, and somehow I don’t like what CoreSync and other Adobe background processes seem to be doing to with memory and cpu. Like it’s in a way as invasive or more invasive than Dropbox but with fewer functional benefits.

I’ve tried Resilio Sync as well and while it gave me a glimpse of hope there was some reason why I stopped using it that I can’t recall off top. Possibly the setup and how it wasn’t as clear cut as I wanted it to be.