Cloud Storage Faceoff: Windows Live SkyDrive Vs Dropbox

Cloud Storage Faceoff: Windows Live SkyDrive Vs Dropbox

With Amazon’s recent entry into consumer cloud storage, we’ve got quite a few competitors offering great and varying options — but which one is the best? Here’s a look at Windows Live SkyDrive and Dropbox, and our top pick for storing your files in the cloud.

These services are a little bit different, so they’re hard to compare one-for-one. We have our preference, but make sure to check out each service individually as one may suit you better than another. If you want to see the verdict on all the services at a glance, scroll down to the bottom of the page for a quick look. For a more in-depth look at every service, just keep reading.

Windows Live SkyDrive


The Good The feature set is simple and concise. Windows Live SkyDrive gives you 25GB for free. It integrates with Windows Live Mail (a.k.a. Hotmail) and other Windows Live services, like the online version of Microsoft Office. It comes with nice viewing options for photos and videos, and makes it easy to view and share your files across platforms.


The Bad The feature set is simple and concise. Aside from a massive amount of free space, you don’t get much with SkyDrive. It’s pretty much just storage. If you need more than 25GB, you’ll need to look elsewhere because what you get for free is all you get in general. Additionally, while you do have 25GB of space, you only have 50MB per file. If you want to upload a file larger than 50MB you’re out of luck, which is a big disadvantage for the service.

The Verdict SkyDrive is essentially 25GB of storage — for free. While it doesn’t have the most compelling feature set if you’re not using it with Windows Live Mail and the online version of Microsoft Office, it is a whole lot of space for a whole lot of nothing. Value-wise, you can’t really beat it… unless you have files greater than 50MB.



The Good Dropbox only gives you 2GB for free, but you can bring that up to 16GB by referring your friends, family, and complete strangers you can coerce into signing up using your referral URL. For $US100 or $US200 per year, Dropbox will up your storage to 50GB or 100GB, respectively, and that’s not including your referrals (which are doubled when you’re a paid customer). Dropbox storage not only includes your stored files, but also keeps copies of deleted files in case you want to get them back. For an extra fee you can keep an unlimited number of copies for easy recovery.

The best part of Dropbox, however, is that it syncs to all your computers. If you keep everything important in your Dropbox, that means you’ve got a backup of all your important files automatically by virtue of them being on multiple machines as well as up in the cloud. If you are syncing between machines, Dropbox will first sync files over your local connection first, making sync a lot faster when all your computers are on the same network. Dropbox has apps for pretty much every mobile device, so you can easily access your files from virtually anywhere. Dropbox also makes file sharing easy as you can simply right click to share virtually anything in your Dropbox or share it from the mobile app.


The Bad If you need more than 100GB of storage (or, really, 132GB with referrals), you’re sort of out of luck. While perhaps Dropbox has a secret plan for digital hoarders that we don’t know about, the published limit is 100GB and that may be too low for people who have a lot of stuff they want to store. Dropbox also does not let you store files outside of your Dropbox (although you can work around that limitation). You also won’t want to use Dropbox for backing up or syncing any complex files or system files to avoid conflicts that could cause serious problems. For example, syncing iTunes with Dropbox across multiple machines can cause problems with your library since iTunes saves your library in a single file. (We have a workaround for this, too.)

The Verdict Dropbox is really great if your needs include syncing and you can limit your storage to 100GB, but if you need more space or just don’t want to pay for it, you may want to look into another option.

What’s the Best Cloud Storage Option?

Good question. What’s really great about all these products is that they’re not identical and offer varying sets of features. What we’ve realised is that it’s not so much about which one’s the best, but rather which one’s the best for you. If you need to sync, go with Dropbox. If you want to pay absolutely nothing and get a ton of storage (25GB), go with Windows SkyDrive. While you could probably rig any one of these services to basically act like the others, they each have their strengths and weaknesses and you’ll have to decide which strengths are more important to you.

Personally — and I think this goes for everyone at Lifehacker — I love Dropbox. If you have more than one computer, it’s almost a necessity. If there’s a winner in my book, it’s definitely Dropbox. That said, these are all great cloud storage services that aim to meet varying needs. If you choose based on what matters most to you, chances are you won’t be disappointed.


  • For $100 you can buy yourself an external hard drive that is more than 100Gb. I prefer SkyDrive though the full name sucks and is far to long. I’m a person that doesn’t want to spend money unless I have to so 25Gb is more than enough for me to back up some files for work and some music for myself.

  • You did not metion Live Mesh which intergraes with SkyDrive and allows you to sync up to 5gb of file between muliple PC’s and Mac’s?

  • Having previously used Live Mesh, I have become a Dropbox convert. It works fanstically well with the iphone / ipad.
    Also, a feature not mentioned is Public file sharing. Dropbox creates a seperate “Public” folder. Any files you please here can be shared with no DB users by sending them a link to the file. An instant FTP.

  • Amazon has something interesting in the works… However it doesn’t seem like it can offer the same features as Dropbox does. Same goes for the Windows SkyDrive actually… Where is developer’s api? Where is iOS support? Does it even come close to supporting as many platforms as Dropbox does? One thing that leaves Dropbox in question is its music streaming capability just like Amazon now offers. Well thanks to the Dropbox’s developer’s api now there is an iPhone app that let’s you stream your music: SongBox Player (

  • Dropbox wins with the cross-platform compatability. I have a couple of Linux boxes as well as Windows and use it to keep my Keepass (also cross-platform) database in sync with all of them.

    I don’t really use it for big files – with so many machines that use it, you could easily chew up a lot of monthly quota syncing big files across multiple systems.

    One advantage that’s rarely mentioned about dropbox is file recovery. It’s possible if you accidentally delete a file from Dropbox to get it back. Not sure what the timeframe is before it’s gone for good, but handy nonetheless.

  • Hi there,

    My company is thinking about using Dropbox for daily file transfers (ie, working from home, not needing to email the document to another email), but some people are concerned about the possible access the general public would have to the files.

    Do you guys have any suggestions of how to keep the info as secure as possible using DropBox? Or is it not advisable to use DropBox if we’re planning on using it for confidential information?


  • Laura, Don’t believe the Dropbox fanboys. Dropbox has serious security flaws and issues (google “dropbox security issues”), if you want 100% secure online file sharing and synching, try SpiderOak. Unline Dropbox, SpiderOak themselves have no access to your data because the encryption/decryption keys are stored on your machine and your machine only.

  • “If you need more than 25GB, you’ll need to look elsewhere because what you get for free is all you get in general.”

    I’m baffled on why you think this is a bad thing when you consider the fact that most online storage providers, including Dropbox are not so generous in matching Microsoft’s free storage offerings. Besides, if you need more than 25GB, simply create another SkyDrive account. In fact, you can create as many accounts as you want with no restriction imposed by Microsoft unlike other providers, including Dropbox that enforce the “One Account Per User” policy.

    “If you want to upload a file larger than 50MB you’re out of luck, which is a big disadvantage for the service.”

    Not true. You can get around this limitation by splittings large files with third-party compression utility or cloud storage tools such as Gladinet that provides chunking function.

  • Dropbox is great BUT be warned…all ‘cloud’ services have a server somewhere (I.e. USA) & subject to the laws of that country….your data could be accessed.

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