The Complete Guide to Backing Up Your Mac – Part 2 – Cloud Backup and Syncing

This is a bit overdue, but welcome to part 2 of the complete guide to backing up your Mac. If you’re looking for a guide on physical backups I would suggest looking at part 1 of the guide. This section will be about cloud backup and syncing.

There are a few things that should be emphasized first before we start this. First, you should not consider this an either-or situation. In fact, it would be better to use a cloud syncing method in conjunction with a local physical backup. Both systems have their pros and cons that compliment each other.

Physical backups typically allow you to grab the entirety of your hard drive should you so choose. Even if you don’t do a full disk backup, you can still backup up your Mac’s profile and settings to quickly restore to. In the event you need to restore, a physical backup will likely be quicker than needing to connect to the Internet (assuming you can). But the more you grab means the more time it takes to backup and restore, and that data is at risk of something happening to it if it and the computer are stored in the same location.

Say a fire happens at your home and you lose your computer in the fire, likely it means you lost your physical backup too (unless you took it with you in a bag)! But with a cloud backup, you know your data is still safe. A cloud backup allows you to backup off-site. Cloud backups also have the benefit of focusing on backing up the most important data, typically your personal documents, pictures, video, etc. While not as complete as most physical backups, most people are willing to take time re-customizing their desktop settings and icons than losing their thesis paper or family photos.

There are other benefits too, as cloud backups let you access these things through the web and across other machines. For some, this is a privacy concern, meaning some third party theoretically has access to your data. With that said, let’s focus on what to think about with choosing a cloud storage provider. Also, I’m going to try to limit this to individual users rather than enterprise level because that’s a whole different ball game.

Storage Space/Price

Google Drive's Free and paid comparison chart, mainly showing users get 15 gigs of storage for free and up to 2 terabytes on a paid tier.

I really tried to split these up but kept running into places where they intersected, so I figured I’d keep them together.

First off, you want to make sure you have enough storage space. It doesn’t matter if it’s otherwise perfect if you don’t have enough space. If you’re looking only at free options, then Google Drive is your best bet with 15 gigs of free storage out of the gate, compared to 5 gigs for most other services like OneDrive, iCloud, and or 2 gigs if you’re Dropbox.

Now even the free tier can come with other caveats or benefits. For example, Google Drive says that any files stored in their proprietary “G-Doc” formats don’t count against your storage. So an essay converted to or written in Google Docs won’t count against your storage limits. iCloud, starting with iOS 15, will let you have unlimited storage for up to 3 weeks when upgrading to a new iOS device in order to help you backup and transfer everything. Note also that all the services that offer email accounts along with your cloud storage will count that against your limit, at least on free and most individual tiers.

If you’re willing to pay, then you’ll obviously get more storage, though that is also at the intersection with your budget. Some services give you the flexibility on how you pay. Google Drive and Dropbox allow you to pay monthly for storage or get a discount when paying for a year. iCloud and, on the other hand, only give you one option: monthly for iCloud and annual for If you’re only hoping to try out a service for a month, paying a yearly subscription out of the gate can be rough.

One last factor regarding storage space is how much storage space you can get on the paid tiers. Much like your payment options, different providers will have different variations on their plans. Most typically don’t give more than 3 paid options for individuals, some offer fewer. Apple and Google give you 3 paid options. Depending on your point of view Apple eek’s out a win on the low end while Google eeks it out on the high end (at least between these two). See Apple’s first paid plan is $0.99 American/month for just 50 gigs. Google and OneDrive both start their paid plans at $1.99/month, but offer 100 gigs of storage instead (and both monthly and annual subscription prices). Next Google and Apple both offer 200 gigs at $2.99. The high end is where we see some differentiation. Apple and Google both offer 2 terabytes (200 gigs) for $9.99/month, though Google still gets the advantage for annual subscription of basically $100/year. actually does better than Google though, even factoring the annual subscription by offering their plan annual plan for the equivalent of $8/month for 2 TB. OneDrive technically is the best price at $69.99/year (or about $5.83/month), but only offers 1 TB of storage max. Dropbox is actually the most expensive, and least flexible, only offering one individual tier for $11.99/month or $9.99/month for the annual option for 2 TB. In other words it costs as much as Apple, but only offers the single tier. Surprisingly a case where Apple gives you more options, though it makes sense give storage space is Dropbox’s entire business model.

So based off storage space and pricing, Google is the winner in storage space at the free tier, Apple wins on the lowest paid tier, OneDrive wins on the mid-tier, and I’m going to give the high-end tier to since you get the most space for the least amount of money (again OneDrive is cheaper at their highest plan but offers less storage).

File Size Limits

Dropbox's notes on file size limitations in their desktop apps, web page, and through API's

On the surface, this may seem like an odd point to bring up. For most people the size of their files isn’t going to matter. However, if you work in video or audio work, have huge photo projects, or massive spreadsheets/databases, this is something to consider. Services, for reasons both practical and secure, have limitations on the size of individual files that users can upload. While this isn’t as big of a deal as it used to be, it’s still worth mentioning if you’re more of a content creator sort. And these amounts can vary wildly. One of the most consistent things is that almost all providers have higher upload limits if you’re uploading from their desktop or mobile apps compared to their web apps.

iCloud is the weakest here maxing out at 50 GB/file whether on web or desktop. OneDrive does better maxing out at 250 GB as of March 2021. and Dropbox actually wins in this category in my book, capping out at 2 TB max file size through their dedicated desktop apps. Their web versions are different stories. Dropbox limits web uploads to 50 GB, much like iCloud. While doesn’t have a hard limit, they do say that upload and web panel performance may degrade when uploading files of more than 500 MB, which is pretty low.

You’ll note I didn’t list Google Drive here, and that’s because Google Drive is a little more complicated. Google Drive’s storage limits are actually dependent on the file type being uploaded. If the file is a G-Slide, then the max size is 100 MB, but if it’s a G-Doc then it’s 50 MB, OR 1.02 million characters long for anything else. And for spreadsheets, it depends not on file size, but on how many columns or cells your have in it and how big an individual cell can be. Any other file types is 5 TB. Now I don’t expect many people will honestly run into issues with this, but there may be a few who are writing the next classic novel or are working in huge spreadsheets that might want to be aware of this. Either way, it seems iCloud is the weakest choice, whereas Dropbox and are the best if you have humongous files.

Platform support

The top of the OneDrive for Mac page showing it as available for download.

On the surface it seems pretty obvious you want your storage provider to work on your app of choice, but there’s a little bit more to it than that. One question to consider is does the app work equally well across the platforms you use, or does it really only work well on one. iCloud is a prime example of this. It’s really only meant for Apple’s platforms, and while it has a Windows app it’s not as slick or integrated into the OS nor offers as much as it does on the Mac. And there’s no Android client. Microsoft does better, offering OneDrive on Mac, Windows, iOS, iPad, and Android, not to mention offering arguably the best mobile office apps in, well, Office. iWork is really good on the iPad and iOS, but Office outclasses it in almost every space (except for Keynote, but that’s a different matter).

Google Drive has the best editing suite on the web but absolutely abysmal mobile apps for editing compared to iWork or Office. Dropbox lacks its own editing suite, but has fantastic integration with Office both on desktop and mobile platforms.

Dropbox get the point for the most platform support though. It is the only one out of these options to have an official, native Linux client. Some of these, like Apple and Microsoft, will likely never have official options, while has promised it’s on the way. Meanwhile Google promised a Linux client early on but has yet to manifest that, and it’s likely vaporware at this point. On the flip side, Dropbox has been slow to adopt some new features of its respective platforms. For many years Dropbox icon support in Ubuntu menubars were missing. More recently Dropbox had been laggard on upgrading its app to natively run on Apple Silicon until the community made a big enough uproar.

Ultimately this depends on what platforms you intend to use and stick by. If you’re confident you’re only going to use Apple stuff, iCloud is a sure bet. If you know you’re going to use Linux and don’t want to use the web version, go with Dropbox. Everything else is somewhere in the middle. I’m going to give points to Microsoft as well for their Office suite working with a lot of. and very well with, other cloud providers.

Privacy and security

The banner from's security and privacy page.

Let’s start with security. Security here means making sure no one outside you, the people you choose to share the documents with, and the company hosting your files can see or access your files (more on that last bit in the privacy section).

For starters, all of these services encrypt your data in transit so no one should be able to snoop on your stuff as you’re uploading or downloading it. Even if someone were to break into their servers, the files wouldn’t be easily accessible to the hackers because these files are also encrypted on the companies’ servers. How much encryption is a little dependent on the service, though it’s not necessarily unreasonable.

All the cloud storage providers use a variations of either 128 and 256 AES encryption, sometimes in combination with each other, to secure your data when it is “at rest”, or just sitting on their servers. As far as in transit, that depends on a variety of things. All the services will use TLS first to secure the connection between your device and their servers when you’re actively downloading or uploading files. The method they use to encrypt it depends on what OS you’re using, the browser you’re using, and even some other tools in place. Some services max out at TLS 1.2, while some can use the more robust TLS 1.3. Some will even allow SSL for older systems. Even then, the encryption algorithm and hash and key exchange they use while the data is in transit is dependent on what version of TLS or SSL they can use with your machine.

Google Drive is the most clear about this actually laying out how they encrypt data in transit and at what levels depending on the standard of TLS and SSL. Others like Apple and OneDrive tend to give a blanket statement about their encryption either giving a minimum or maximum encryption standard being used. gets the most credit for its white paper where it lays out how it encrypts not just the data but shared files, your password, and more as well.

That’s actually something else to consider in your security. It doesn’t matter if your files have the greatest encryption on every single level if your password is just “123456”. All of these services push you to use longer secure passwords. Some, like, will also add another encryption layer onto passwords it considers too weak. All of these services support Two Factor Authentication as well. Besides using a phone number, which is technically just Two-Step Verification not Authentication, all the major services encourage you to use a higher level. All but Apple support 2FA using a dedicated 2FA app like my preferred favorite app Authy, Google Authenticator, LastPass Authenticator, Duo, etc. Apple instead asks you to approve your login from another device signed into your Apple account and type in a code from the device you approve from. To be fair, it’s a good system, but can be more restrictive in a mixed-device setup.

Finally, one of the things many us nowadays want to ensure is our privacy. More specifically, we want to know if and how the companies can access the data we store and their servers. It’s not too surprising that many companies allow us to store stuff with them so long as they can ensure it doesn’t break their rules or is illegal nor is it unfair. You don’t mind holding onto something for your friends, but if that item was used in a terrible crime you wouldn’t want to be caught holding it. But, what if that data was used to sell ads against you, or given to third parties to do stuff with. Going back to the holding an item for a friend example, if you gave your friend an item to hold to for you, and you found out they were showing it off to their friends or taking it with them other places where it didn’t need to go, you might be concerned.

On a more serious note, you may have concerns depending on where you live. You may live under a government that may punish you for things like the color of your skin, your religious beliefs, who you love, or any number of other reasons. What are the risks to your data?

Here is the best. It implements zero-trust or zero-knowledge encryption tools. Meaning it can’t see what you upload or download, what you access, and couldn’t unlock it whether they were asked to or if someone hacked them. As far a third party privacy goes, does say they occasionally work with third parties. Typically, these are third parties that you authorize, but other may be enlisted to help improve their services. However, none of your files are at risk and your data and info will never be sold. says it limits the information it collects to personal information relevant to your service, your IP and log times, and any payment information if you’re on a paid tier. They will provide this information to governments if requested such as if your account is associated with illegal activity. Again though, it cannot be the files themselves. And, because is a Canadian corporation, they have a Privacy Officer and follow the guidelines under the PIPEDA (Personal Information Privacy and Electronics Documents) Act. You can read more about it on their privacy page.

Apple is probably next best here. Apple generally doesn’t not share your data or files with any third parties that you don’t explicitly authorize. They do not use zero-trust encryption though, meaning that if law enforcement in your country requests it, then any data that you have stored in there can be given to those authorities. So here, iCloud is much more useful for prevent ad-snooping.

Dropbox serves as middle ground here. While they initially started with no-trust encryption, they eventually changed to one that they can open to share with governments if requested. Furthermore, while they don’t sell the data to third parties, they may enlist third parties to help manage it and have been known to track users across other apps and sites to show ads to them.

OneDrive and Google Drive are last. Both companies have ad businesses and will you use the data in your files and emails to sell you things. Both do share data with third parties for compliance and improvement purposes, though they typically are keeping it for their own purposes more than selling it to other parties. Still, they have very strong hooks into the entire web and can get a much clearer picture on your than Dropbox across all your sites. And, like most of the others before it, they will decrypt and share your files with law enforcement if requested.

Overall, if you’re worried about government surveillance, then you should think hard about if you want any files stored in the cloud. But if you want the most security and privacy, then go with If you’re more concerned about ads and tracking than governments serving you a warrant, then go with Apple.

Other Benefits

iCloud's description of Hide My Email for iCloud+ subscribers.

A lot of these platforms have diversified, especially as the competition has grown. All have fairly robust web portals and mobile apps, and Apple, Microsoft, and Google offer things like free email, calendar, etc., but some offer some unique features beyond that.

Dropbox, for example, recently added contact syncing and a password manager to line up with the other big players. They have announced a new “Replay” feature, allowing better collaboration with other Dropbox users on audio and video projects. They also have the “Vault”, which is a dedicated encrypted folder within Dropbox that has an extra password separate from your actual Dropbox password. And Dropbox allows you to send a link to request files from others so they can upload files to your Dropbox even if they don’t have their own account.

iCloud offers a bunch of new features in the latest version of iOS and Mac OS include email aliases and hiding your email, the “Private Relay” function that acts as an extra privacy guard, and their iWork web editing and really good Notes app. OneDrive and G-Drive also offer great web editing suites as well, though only Apple and Microsoft have desktop apps.

Dropbox, Google Drive, OneDrive, and iCloud will all sync your desktop, documents, and pictures folders from your computer to the cloud (though iCloud only does that on Mac while OneDrive only does it on PC currently).

Honestly it’s not really fair to declare a winner here just because the feature lists are extensive, not everything is an even comparison, and are not really essential for all use.


Ultimately the best cloud storage provider is up to you and what your needs are. But there are some definite benefits and weaknesses to each service. Here is where I would sum things up.

Best Space to Price Ratio– Google Drive/
Worst Space to Price Ratio – OneDrive
Best File Size Limits – Dropbox
Worst File Size Limits – iCloud
Best Platform Support – Dropbox
Worst Platform Support – iCloud
Best Security –
Worst Security – null (All 4 remaining are about the same)
Best Privacy –
Worst Privacy – Google Drive
Editor’s Choice: 1st:, 2nd: Dropbox

Ultimately these are just my opinions on just 5 major services, but there are dozens of others and what you need will determine what platform is best for you. That said, I’d be happy to hear you opinions and what you like to use. Let me know in the comments below.

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