Are you a Mac or iPhone user agonizing over whether Dropbox or iCloud is more deserving of your investment? We here at Cloudwards feel your pain. Trying to pick cloud storage favorites is a bit of an obsession of ours. Lucky for you, we’ve developed a simple method to help ease the decision making process:

We make them fight.

In this article, we’re going to pit one service against the other to see who comes out on top. We’ll be gauging the two services on plans and critical features like syncing, sharing and security. If iCloud isn’t your thing, you can also check out our list of other Dropbox alternatives.

We have compared iCloud to other services before, notably IDrive, where it didn’t come out too well; this time it isn’t much different as in the end we prefer Dropbox, even if just because it offers greater versatility. However, it should be noted that it isn’t quite the knockout decision it would have been a few years ago, as iCloud has made some serious improvements lately.

The Battle: Dropbox vs. iCloud

Over the course of five rounds, we’ll compare Dropbox and iCloud point by point to see who meets its users needs the best. See you on the other side. If you’d like to check out our video review of iCloud, you can find it below. We also have a written Dropbox review.

iCloud Review | Find the Right Cloud

Round One: Pricing and Plans

First off, let’s take a look at which of the two services will give you the best bang for your buck.


Dropbox offers four different plan tiers:

  • Basic: 2GB
  • Pro: 1TB
  • Business: Unlimited
  • Enterprise: Unlimited

The basic plan is free. However, several important features aren’t available unless you upgrade to a paid subscription. I’ll cover these in round three, but you can also read our Dropbox pricing guide.

The Pro and Business plans can be subscribed to on either a month-to-month or annual basis. With an annual plan, you’ll save a little on the total price — but not by very much. Do note that the 1TB plan is pretty affordable when compared to others.

Dropbox Plus
  • 2000 GB Storage
1-year plan $ 9.99/ month
$119.88 billed every year
Save 16 %
Dropbox Professional
  • 3000 GB Storage
1-year plan $ 16.58/ month
$198.96 billed every year
Save 17 %

Enterprise plans aren’t priced on the Dropbox website. You’ll need to contact them directly for a quote.

Both Basic and Pro users can earn additional space by referring others. Basic users can refer friends to earn an additional 500MB per referral, up to 16GB. Pro users get 1GB per referral, up to 32GB.


iCloud offers users 5GB of free storage space. For users just looking to back up their iPhones and iPads, that might be enough. When it isn’t, Apple offers several monthly subscription options:

Storage spaceMonthly cost

A few things of note:

  • Above prices are for the U.S.; worldwide prices fluctuate wildly
  • There are no discounts for signing up for a full year
  • iCloud doesn’t offer business plans
  • iCloud doesn’t offer referral bonuses

Also, your iCloud space is shared with iOS device backups, your iCloud Photo Library and iCloud email.

Round One Thoughts

When it comes to plans, Dropbox’s biggest advantage over iCloud is that it accommodates SMBs with an unlimited business plan. iCloud, meanwhile, is priced exclusively with the individual in mind.

However, in that regard, it really shines. The luxury of not having to jump straight to a 1TB account is something Dropbox — and most other services in our cloud price comparison — doesn’t offer. The flexibility of having to only to spend in accordance with your needs is going to benefit the average user more than a business a plan will.

Round One Winner: iCloud

Round Two: Syncing

Being able to keep all your files up-to-date across all your devices is a great feature that not all cloud storage services offer. How do Dropbox and iCloud do?


Dropbox offers a great range of features to help you manage your data. Like any good cloud storage service, that starts with the ability to sync content across devices.

Supported desktop platforms include:

  • Mac: Snow Leopard and higher
  • Windows: Vista and higher
  • Linux distros far and wide

Mobile supported is offered for:

  • iPhone/iPad: iOS 8 and higher
  • Android: OS 4.1 and higher
  • Windows Phone: 8.0 and higher

Dropbox performs syncs incrementally, which keep things running smoothly. The service also minimizes bandwidth impacts by automatically throttling sync uploads to 75 percent of the max speed. Downloads are set to 100 percent. You can manually change either set of settings if you want. Read our guide if you have trouble with Dropbox not syncing.


Despite being designed for Apple products, iCloud can be used to sync content with Windows, too. Desktop applications can be downloaded for:

  • Mac: Yosemite and higher
  • Windows: Windows 7 and higher

However, mobile apps are only available for iPhone and iPad.

iCloud syncs aren’t performed incrementally. This can be an issue when working with large files. Also, iCloud doesn’t let you throttle sync speeds.

Round Two Thoughts

Despite having a Windows application, Dropbox is a better choice than iCloud to connect your devices. More platforms means more accommodation of your device preferences. In fact, with incremental uploading and throttle controls to help manage sync speeds, it’s probably a better choice even if you are someone who prefers to use Apple’s ecosystem above all else.

Round Two Winner: Dropbox

Round Three: File and Folder Sharing

Sharing files with others in your organization, or even just your friends, is one of the main benefits of storing data in the cloud. Which of our two services does best here?


Dropbox makes it easy to share your content from its web interface. You can either create a shared folder and invite others to work in it, or you can create a link to your content that anybody can access.

Shared items can include folders or files, but only folders can have edit permissions attached. View or edit permissions are set when creating the share.

There are options to password protect links and give them expiry dates, but you’ll need at least Pro account to use these features. If you’re concerned about losing track of your shared content, you can use the “sharing” and “links” tabs of the web tool to audit what access has been granted.


Folders stored in iCloud cannot be shared with others. You can share files, but you’re limited to iWork files. iWork files are those that are created using iCloud’s native productivity apps, which I’ll touch on coming up.

Round Three Thoughts

There’s really not much to say here. Dropbox is a very good tool for online collaboration, while iCloud is very insular and not designed for working with others.

Round Three Winner: Dropbox

Round Four: App Integration

Storing data is one thing, working on it is something else: how do our two contenders deal with integrating apps that let you get the most out of being online?


Dropbox has its own native productivity app like Google Drive, OneDrive and iCloud do, but it isn’t as comprehensive as its competitors. However, it has had a strong integration partnership with Microsoft Office since 2014, which is a selling point for many.

In fact, Office Online is automatically configured into the Dropbox website, so there are no further steps required by you. Any Word, PowerPoint or Excel files you have stored can be opened and edited in Office Online, right from the interface.

This allows real-time collaborations on shared content, too.

There’s no way to create a new Office Online document from Dropbox. But you can just head over to Office website and set up an account for free. You’ll then have full access to what remains one of the best productivity suites available. Afterwards, you can even access Dropbox directly from Office Online.

Note that the rules are different for Dropbox Business accounts, which require an enterprise Microsoft account.

Dropbox has several other technology partnerships that enhance its value. Noteworthy examples include handy small business apps like:

  • Adobe: share and view PDF files
  • Slack: real-time messaging for teams
  • Asana: track and manage work projects
  • IFTTT: create and automate app relationships


iCloud does have its own productivity apps: the popular iWork suite. This includes:

  • Pages: for word processing
  • Numbers: for spreadsheets
  • Keynote: for presentations

With regard to capabilities, iWork holds its own against Microsoft Office. No, Apple doesn’t offer iWork apps for Windows or Android. However, you can use it for free from any device capable of accessing iCloud, regardless of platform.

Better yet, Apple allows third-party apps to integrate with iCloud — including Office.

Other apps include:

  • Goodreader: for PDFs and other files; includes annotation capabilities
  • Todo: for creating task lists
  • iA Writer: for distraction-free writing

Some of the best iCloud-enabled apps are those produced by Apple. This list includes Safari, Calendars, Photostream, Reminders, Notes and, of course, iTunes.

Round Four Thoughts

Despite not developing their own apps, the folks at Dropbox have done a nice job leveraging partnerships that will appeal to users interested in getting work done.

Apple doesn’t chase down such alliances as vigorously as Dropbox, but they don’t need to: They’re really good at making software. They do let developers integrate with iCloud, so there are some decent third-party options. However, it seems a lot of the big names you get with Dropbox aren’t available with iCloud.

Ultimately, deciding whose integration library is the best depends on your needs. Dropbox is more geared towards teams, while iCloud is more geared towards individuals. In case you make the wrong choice, you can read our guide on how to remove Dropbox from Mac.

Round Four Winner: Tie

Round Five: File Protection

Protecting your files is as important as sharing them. Though Dropbox is not zero-knowledge provider, while Apple is, there are other considerations to take into account as well.


Dropbox follows the industry standard by protecting in-transit files with TLS/SSL encryption. Files traveling through this secure tunnel are encrypted with 128-bit AES.

Upon arriving at the data center, your files are decrypted prior to storage. Content is then re-encrypted with 256-bit AES. However, your metadata (file names, dates, sizes, etc) remains readable.

To help secure their account further, users are offered the option of enabling two-step verification. When this feature is turned on, you’ll need to enter both your password and a six-digit code to access your account. This code can be received via text message or through the Dropbox mobile app.

Normally, Dropbox retains deleted files for 30 days to protect users against accidental deletion by themselves or others. Additionally, all file versions are retained for 30 days.

Dropbox Pro users can select a subscription add-on called extended version history (EVH) for $3.99 per month. EVH saves deleted files and all file versions for up to one year. Dropbox Business users automatically get indefinite file version and deleted file recovery.

The web interface also includes an “events” tab that lets you monitor activity on your account. This is a good way of to keep track of what actions others are taking on your shared content.


Like Dropbox, iCloud protects your data as its travels between device and data center with a secure TLS/SSL tunnel using 128-bit AES.

Your content is also stored while at rest on the cloud. Apple doesn’t make it clear what encryption level they use other than to say that it’s at least 128-bit AES. As mentioned before, that level of encryption should be fine for the foreseeable future.

I couldn’t find any information from Apple on whether or not they encrypt metadata. I would assume not, since most cloud storage services that don’t offer zero-knowledge encryption also don’t encrypt metadata.

While zero-knowledge encryption isn’t available for all of your iCloud content, it is for iCloud Keychain. iCloud Keychain is a manager for storing passwords, credit card numbers and other information in iCloud. Zero-knowledge encryption prevents Apple employees or hackers from reading that data.

Apple offers the option of two-factor authentication as an added security requirement. When you try to sign into iCloud on a new device for the first time, you’ll need to provide both your password and a six-digit code. This code is automatically displayed on “trusted” devices.

iCloud lets you restore deleted files for up to 30 days. There’s no overarching versioning system in place for iCloud. However, you can restore a limited number of iWork versions.

Round Five Thoughts

Both Dropbox and iCloud do a pretty good job protecting your content with at-rest encryption and two-factor authentication. However, both would do well by encrypting user metadata and granting users the ability to opt into zero-knowledge encryption.

This is especially true since both Dropbox and iCloud have been subject to high-profile hacks. Details of 68,680,741 Dropbox accounts were stolen in 2012, while iCloud accounts belonging to multiple celebrities were broken into in 2014.

Dropbox does a better job than iCloud with version and deleted file control by extending it to all of your stored content. I think that’s a reasonable tiebreaker in deciding which service best protects user content today.

Round Five Winner: Dropbox

The Verdict

iCloud has come a long way in the past five years, but it’s clear to me that it isn’t a Dropbox replacement just yet, even for Mac users. Where it falls most short – syncing and sharing – are two of the most fundamentally important aspects of cloud storage.

However, maybe it’s wrong to look at iCloud as competition for Dropbox in the first place. Use Dropbox to enhance your work collaborations and take advantage of iCloud’s flexible pricing structure, and you can get the best of both worlds. In iCloud’s case, that’s more storage for iPhone contacts, photos, iTunes and other elements of a more personal cloud experience.

Still, when it comes to investing more substantially in one or the other …

Winner: Dropbox

Do you think we got it right? Let us know in the comments below, thank you for reading.

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29 thoughts on “Dropbox vs iCloud: Best Choice for Mac Users”

  1. The last paragraph says it all. I am in the process of choosing a cloud storage options. This article helps me identify main functions that suits my needs. That will be my focus and hopefully will help in the decision making process. Rather than picking the best plan offered, it should be based on the functionality required.

  2. I mostly agree with this analysis, but it leaves out some important criteria (to me at least) like customer service, privacy policy, and so on, things that you really dinged Dropbox for in a separate review. For instance, Apple would seem to have a MUCH better privacy policy. That might be important to some of us. Also, there are other apps, like Ulysses, that are pro grade, have a strong user base, and ONLY work with iCloud. It would be even more helpful, in these comparison, if you would use your entire checklist.

    1. - Chief Editor


      You’ll find a separate Dropbox review linked in the article that should answer all your questions.


  3. I have used Dropbox for years and love it. It saved my bacon a couple times when I left my pc and open files on it and it lost power due to a brown out. I thought I lost hours of work, turns out it was all there in recent files in Dropbox. One thin I like to point out is it does easily store photos, I have thousands on my account with no issue

  4. Dropbox is way better for seem-less and instantaneous photo file uploading.

    I can’t get over how stupid it is that iCloud Photos doesn’t let you access the actual photo files from your Mac desktop, except through a browser.

    Don’t underestimate how much this sucks and how dumb Apple looks for not being able to match this capability of Google dropbox.

    With Dropbox, you can access photo files(i.e. *.jpg), in a folder on your desktop. However with iCloud you have to open up a Chrome browser to go through your photos.

    Despite my desire to use Dropbox, I have found over time that Apple devices are completely USELESS unless you have adequate cloud storage. This is for MBpro or iPhone. So since I have to buy a 1TB plan anyway, I decided to cancel dropbox and try to make apple work.

    But it sucks. iCloud sucks. Im telling you. But i’m still using it.

    1. uhhhhm, I think you’re missing something here.

      there’s an app for that on your mac called “photos”. think of it as a finder window exclusively for browsing your fotos & videos, that also has in-baked organizing and editing capabilities.

      If you need to grab the actual files for whatever purpose, it is as easy as drag&drop from the app window.

      It is actually pretty simple, no browser required.

      apart from that I agree that icloud drive has some annoying limitations

  5. I fully agree with the article and also with Dustin’s latest comment. Dropbox is so far the best cloud storage service I have used, but I can’t understand why don’t they offer a family plan. (What if I have a wife and kids, shall we buy 5 accounts for 50 bucks?)

    On the other hand, iCloud’s photo “handling” really sucks. This is such a basic function, it is hard to understand why don’t they implement it. (That is, that one could put photos in any folders AND still handle them as a photo library.)

  6. After working for years with Dropbox, i agree that Dropbox wins today from the i-Cloud.
    Espacialy after the improvement during the latest years with the Office online integration and not less important, the integration of dropbox options trough windows explorer and the local software access to the stored files.
    The 1Tb upgrade as first/only upgrade option for 9.99€/month is the disadvantage.

  7. Excellent article. It’s so tempting to switch to iCloud to streamline things but clearly iCloud is not there yet.

  8. How can I delete photo’s from dropbox? I want to clean up some space because my dropbox is full. I do not want to upgrade. I would like to prevent dropbox from saving my photos all together since I have them on my iPad, iPhone and pc. Can you help. Thanks

  9. Reconsider the Fact that files at Dropbox will be de-crypted and encrypted again with a key that the vendor controls. This means, that the vendor CAN access contents of files and the vendor CAN be forced to provide decrypted content to e.g. your stinky friends at the NSA easily.

    On the other hand Apple is not yet fully transparent in it’s guarantees – anyway it sounds more secure than dropbox at the moment and this makes it – for sensitive information – the better choice. But – and that’s important – Apple makes it very, very easy to lower personal security by allowing photo analysis, siri etc. – so if one tries to force Apple to provide information, it might be less information – but probably this information is enough to perform a targeted attack to the desired individual…

    The sad truth is: Do not store important and/or confidential information on remote servers – especiialy if you do not control them…


      Thanks for the comment, Jack. We talk about that some in other Dropbox articles. The best approach to using Dropbox is probably to pair it with Boxcryptor or a similar service.

    1. - Chief Editor

      No, because Dropbox doesn’t offer one 🙂 Had you read the article before becoming all hard-boiled, you’d have seen that we very clearly explain and define our choices, every step of the way.

  10. Interesting comments. I use both, but one big advantage of Dropbox seems to be that I can be much more selective of what I store there. I don’t want all my documents in the cloud, only this year’s, to keep it focused and tidy, not 20 years’ worth. Happy to be corrected if I’ve overlooked something. Thanks

  11. To pay for my 50GB of icloud I buy an itunes gift card in my local store, I redeem it and I am done. That’s what made me choose icloud over dropbox.

  12. I’m a hardcore Mac user and I installed and used Dropbox first when it released. Was so happy that I got a bunch of my clients and friends etc. to sign up and earned a lot of free space.

    Then, became a paid G-Suite user for my graphic design studio email service and I though Google Drive would be perfect with so much space available as part of my plan. Switched to that but unfortunately learnt that MS Office refused to connect with it epically when I needed to access documents etc. on my iPad on the move.

    So then I thought let’s switch to One Drive as it’s part of my Office subscription but it totally sucked in syncing correctly and also didn’t play good with lot of other apps. So then was wondering what to do.

    Being a Apple fanatic, always wanted to align myself with their cloud service but can see and know that iCloud is a pure Apple iWork friendly service which has not got the kind of features and versatility that Dropbox has.

    So have come full-circle back to Dropbox. Planning to sign up for the Pro plan now. The only downside I see is that for backing up WhatsApp etc. on the iPhone, one still needs to subscribe to Apple’s service as well.

    So basically at the end of it, I am not too happy that I will be paying Dropbox, Apple, Google and Microsoft all for their services. It’s just ridiculous!

    Oh and let me not start thinking about the video and audio streaming service subscriptions to add to this!

    Clearly, the tech companies have found ways of making far more money by moving everything online now!

  13. A big difference for those who are not geeks: there is no phone help or screen-sharing on Dropbox, only chat text, while you can talk to real humans who speak English on the Apple help line and screen-share. I could not get Dropbox work on a Mac, obviously because of lack of help features on Dropbox (I am not a Geek). So I dropped Dropbox (pun intended!)

  14. I had the misfortune to think that iCloud would be an intelligent way to keep my files safe and accessible. It caused me months of headache, months of payjng for a service i couldnt use and more hassle to get everything back on to my computer – even IT people couldnt understand why connection and download was so bad. Google docs connects faster wherever i am & easier to access, so much better. I havent tried Dropbox.

  15. Just made the switch over from Dropbox to iCloud. Not looking back. When you sync photos to dropbox from your mac it creates new file names as in (1) if you have over 10,000 photos from lets say your iPhone because it can’t distinguish between 2 photos with the same name. and Dropbox will crash when trying to upload from the photos app on mac. And even when just uploading using the desktop client, it crashes. With iCloud photos are seamlessly uploaded. I was hesitant on using another Apple service at first but they haven’t disappointed.

  16. After getting a new Macbook, and restoring from a backup, I could not get my iCloud drive to sync. I tried everything, and tech is my career. Just switched to Dropbox, and no problems.

  17. After iCloud stopped syncing on my MacPro running Max El Capitan in the middle of a project, I am currently shifting over to dropbox, especially after finding out, that dropbox now even desktop, download and document shares and this also in a better way on El Capitan than iCloud does.

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