Dropbox versus iCloud

@katiefloyd and @MacSparky have had some robust discussions around this topic lately. I found this Seth Godin blogpost interesting and related.

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@Kaskew It’s not that I don’t believe Seth’s experience with Dropbox, but for me, it has been pretty much the opposite. I’ve had so many problems with iCloud not synching my files that I just didn’t use it for years. Dropbox on the other hand has ALWAYS synched my files and when it couldn’t it made a separate file with the date when there was a conflict but I have never lost a file. I guess we are all biased because it depends on our own experience. Just my 2 cents.

Thanks, Jeff. I was an early adopter of Dropbox and my experience with them is similar to yours. I was not an early adopter of iCloud missed out on their early missteps.

I used to have iCloud problems (slowness, sync fails) but as far as I can tell I haven’t had a single problem with synced iCloud files in more than 2 years. Dropbox has always been solid, but has become a bit superfluous to me for the most part, replaced by iCloud (as well as Droplr/Cloudapp for quickie file/screenshot sharing).

Since 2015, when several investors wrote down the value of their Dropbox stakes, the company has taken pains to focus its business. It saw the writing on the wall - that a consumer-focused business wasn’t generating the sales and growth it needed. (Crashplan saw it too, years later.) So Dropbox scrambled to reinvent itself for business, offering document collaboration and buying out companies to supplement its service by offering Paper, Carousel, and Mailbox (the last two of which failed in the market and were dropped). They’re mainly competing with Box.com and OneDrive and Google Drive, I think, though their Mac/iOS offerings are strong.

Dropbox had its IPO this past March, and its price is at a near-low, at $26 and change, down from a high of $43.50 in June. Corporate-focused Box.com has also struggled recently, underscoring the difficulty in competing with Microsoft, Google and Apple, whose products are increasingly integrated and getting better.


Unrelated to the podcast, I decided to finally split from Dropbox recently. I just find that for my personal use, iCloud does everything I need and so by quitting Dropbox I can have one less app running on my Mac (one that constantly requests unneeded permissions).

If I did anything that might benefit from the versioning I’d reconsider, but Time Machine is enough for me in that regard.


Personally, I’m still a big Dropbox fan, but I’ve come to rely on it less since moving most of my day to day operations to an iPad. Versioning is great, but file conflicts in some of the apps I depended on drove me nuts. I’ve since moved my more important file sync requirements to iCloud, and I’m happy thus far.

Also, iCloud became more attractive with iOS11 and Files.app. Still not perfect, but good enough for now (for me!).

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Add me to the iCloud bandwagon. With iOS 11 I dropped my DropBox down to the free space which I still use for sharing files with a couple clients. I only need a few gigs for this and the 1TB was too much.

I bumped up my iCloud to cover my photos and files and it’s been great between my iPad Pro as primary device but synced to an iPad Air, iPhone and Mac.

My only critique as that sometimes the sync takes too long. Mostly it seems to be a case of the Mac being a bit slow to notice changes or to push it’s own changes. Not a deal breaker though.


Is there a way to share iCloud files with others whether or not they are in the Apple ecosystem? My use case for Dropbox is sharing files with clients—you know, like a drop box…

While I don’t use this feature a lot, Dropbox does integrate with other 3rd party services like IFTTT.

I use Dropbox for my photography side project because sharing is pretty straight forward. I’ve tried other solutions, but people always seem to have a problem accessing their stuff. I haven’t had that issue with Dropbox.

I use iCloud for my personal stuff. I live in an Apple world and don’t need to share anything. It just works. I also use AWS S3 buckets to archive stuff. I have a management rule set up to move stuff to AWS Glacier.

For work, it’s OneDrive because we are an Office365 organization.

I do wish there was “one to rule them all” instead of having to pay for three,

I dropped Dropbox a couple of years ago. We have a family Office 365 which offers 1TB OneDrive for each user, and the whole bundle comes cheaper than Dropbox. So between iCloud and OneDrive I don’t need anything else.

PS: I thought of testing Dropbox recently for 15 days, I cancelled subscription before its renewal, I didn’t see any added value.

@mina and @wweber have introduced a new concept for me. I have not used OneDrive from Microsoft. Can eilther of you elaborate on how it functions; strengths and weaknesses? How is it similar and/or different than DrobBox and iCloud?

File sharing is why I still pay for DropBox @DeadSalmon

@Kashew I also use OneDrive but for backing up stuff on my Synology with Cloud Sync, which I setup a one way to the cloud sync. The one BIG difference I had seen with dropbox is that it doesn’t do block sync, but has to reupload your whole file if you make a change. Dropbox only copies the block that has changed, which is MUCH faster. If you just put stuff there but don’t change it often, you won’t see a difference, but if you put your working file for sharing and stuff, it might make a difference. I haven’t checked if Microsoft has change this behavior in the last two years but at least that’s how it worked when I looked at it.

I answered a similar question in another thread. I had Dropbox but dropped it (no pun intended) in favor of iCloud for my personal stuff and OneDrive for my work-related files. OneDrive is part of the Office365 subscription that I have through my office. I can say that OneDrive works great on both iOS and macOS. In iOS, the app integrates with Files, so you can access everything on all your iOS devices very easily. On macOS, the app also integrates with the finder, and works just like an iCloud syncing folder. You can easily share folders with others in both the iOS and macOS apps, which makes it easy to share big files with clients in my case. Syncs are fast and accurate. If you have an Office365 subscription, you get 1TB of storage, which is more than enough for me and most people.

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OneDrive is closer to Dropbox than to iCloud. It has sharing capabilities similar to Dropbox. I have all my photos sync to OneDrive on my iPhone as a backup to iCloud.
Other than versioning which is very expensive on Dropbox, it has everything that Dropbox offers.
And as I mentioned; on top of all of that you get Office 365 on five of your devices.


Has anyone seen rigorous or formalized testing for iCloud reliability recently? Tests like throwing hundreds/thousands of files at it, modifying some at different clients, testing how long sync takes, and then verifying integrity?

I’m really hoping iCloud is gonna come through…but so far logging into a desktop iMac I haven’t used for a few months, Dropbox has updated > 13,500 files and iCloud is just sitting there showing old modification dates on everything. All the changes I had made on my laptop appear on iOS devices but the iMac isn’t syncing a darn thing.

This is really puzzling…native apps and 1Password sync fine but Ulysses, Notability, and everything using iCloud Drive don’t.

Two things. Firstly, if I could point to one program that hasn’t missed a beat in the decade I have been using it and have NEVER had an issue, its Dropbox.
Secondly, I see Apple is facing a class action lawsuit for passing iCloud off as where your files are stored, yet they are really over at Amazon AWS cloud(s). Seems to me to be somewhat misleading from someone such as Apple who make it their business to be upfront about everything. Might be worth keeping an eye on what the US Justice system thinks of this?

I do not recall Apple ever claiming that all iCloud data only sat on their own hardware, do you? Indeed, the iCloud terms make numerous references to partners providing the services… Over the years they’ve utilized Amazon Web Services, Microsoft Azure, and Google Cloud Platform for iCloud functionality, maintained by them under the iCloud banner. Does iCloud look or act like AWS to a consumer? No, of course not.

It was reported back in 2011 that Apple used Azure, and it was no secret when Google Cloud got a big Apple contract last year. But the fainting couches seem to be full at the esteemed plaintiffs’ offices.

Despite committing $10bn to data center investment over five years in 2018, the company acknowledged in its iOS Security Guide that it stores encrypted file chunks on both Apple and third-party storage services like AWS and Google Cloud.

So I’m a little perplexed by the hyperventilating going on about this, and I wonder how plaintiffs expect to prove they were damaged. Meritless? Frivolous? We’ll see.