Dropbox vs. Windows Live Sync Beta 2011 : Feature-by-Feature Showdown

Dropbox LogoEarlier, I gave a rather ebullient guided tour of Windows Live Sync Beta 2011 (which will be known as Windows Live Mesh when it is officially released), touting its groovy potential as a backup tool and cloud storage solution. But since that brief honeymoon phase, I’ve had a chance to move in some of my stuff and I’ll have to admit that I’m having trouble getting comfortable. It seems that much of the pampering I’ve received from old faithful Dropbox has given me some pretty high expectations when it comes to cloud-based syncing and in spite of my optimistic review, I think I’m going to have to stick with Dropbox—for now. Here’s why:

Note: Before we begin, a quick explanation about the name—Windows Live Mesh and Windows Live Sync used to be two separate products. although they did essentially the same thing.  Windows Live Sync Beta 2011—which became available as part of the Windows Live Essentials Beta 2011 package in June 2010—was a combination of the two earlier products. Now, Microsoft has decided to rename what is now available as Windows Live Sync Beta 2011 and call it Windows Live Mesh 2011 once it hits the official release along with Windows Live Essentials 2011, thereby eliminating both previous products. For the purposes of this article, we’ll refer to it as its current name: Windows Live Sync Beta.

Client Support – Advantage: Dropbox

Windows Live Sync Beta made an impressive stride towards coexistence between operating systems by including an OS X client, but Dropbox takes the cake by supporting Linux, Windows and Macintosh. Not only that, Dropbox’s desktop client makes it to each of these operating systems with its features fully intact. The same can’t be said for the Macintosh version of Windows Live Sync Beta, which doesn’t support remote connections.  (Granted, Dropbox doesn’t handle remote connections at all, so maybe it’s not fair to count that against Windows Live Sync Beta.)

Sharing and Public Folders – Advantage: Dropbox

Windows Live Sync Beta’s public folder and file sharing capability is really just handled by Skydrive. And when it comes to sharing files with Skydrive, the experience is clunky to say the least. It’s all done via email invitations, and if the recipient doesn’t have a Windows Live account, they are out of luck. You can share folders publicly via Windows Live Spaces, but again, it’s another step, another sign up process and another layer of “stuff” to navigate.

Dropbox, on the other hand, is very intuitive—in fact, it’s so friendly, it’s downright social. You can right-click and get a shareable link right from Windows Explorer or the mobile app and anyone can view it. Dropbox even has its own URL shortening service, making it highly Twitter and Facebook friendly. No sign-ups or registrations required.

Remote Connections – Advantage: Windows Live Sync Beta

There’s no contest here—Windows Live Sync Beta has it, Dropbox doesn’t. It’s a small victory, however. In spite of Windows Live Sync Beta offering one of the most user-friendly remote desktop experiences I’ve seen, I can’t say that its something I personally look for in a cloud sharing/syncing application.  Normally if your geeky enough to need to connect into a remote system, you will have 4 other ways to remote into your home/work box anyway.  Still, point Windows Live Sync Beta.

Mobile Support – Advantage: DropboxDropbox iPhone App

Same story here, but in reverse: Dropbox has it, Windows Live Sync Beta 2011 doesn’t. Dropbox has a stellar iPhone, iPad and Android app that goes above and beyond in terms of functionality. You can pull up files from your Dropbox folder from wherever you are and you can even upload videos and photos directly. I’m also a pretty big fan of the Favorites feature—it lets me take my daily checklist that I usually keep in my Quick Launch bar with me wherever I go. For the more ambitious, you could even include multimedia files for on-the-go accessibility. You can also grab shareable links and put them in an email or copy them to your clipboard in a snap.

With all that being said, the previous version of Windows Live Mesh did have some mobile support—you could upload images via Not quite an app, but it could mean that Mesh 2011 might carry over some of its mobile functionality into its official release.

Web Features – Advantage: Dropbox

This one was a bit closer—Skydrive has the distinct advantage of being hardwired with Office Live Workspace, which gives you a sort of best of both worlds between Google Docs and Dropbox. Skydrive and Office  Live Workspaces makes complete sense for handling Word files, spreadsheets and other collaborative documents.

Windows Live Sync Beta may have won this one—that is if Dropbox’s web-enabled features weren’t so excellent.  Namely, I’m talking about the Undelete and Previous Versions features. Dropbox’s ability to recover old versions of files has saved my skin (and hours of work) more than once. And while saving me from the consequences of being a clumsy oaf who occasionally overwrites or deletes a critical file may not be to my long-term benefit, I’m extremely thankful that for now, I won’t have to learn any hard lessons about backing up files. Speaking of backups…

Backup FeaturesResults Pending

The ability to perform unlimited syncing between machines with Windows Live Sync Beta really had me excited. The problem: it doesn’t work yet. At least not for me. I had this master plan where I would sync my iTunes folder across all of my machines—40 gigs in all—so that when I made changes to my main machine, the songs would automatically get sent to my other computers without an additionally importing. However, I never made it past the initial syncing phase because about 1 percent of the way through, the WiFi in my entire house went dead. I’m not saying that it couldn’t have been Comcast’s fault or my router’s fault—but I will say that as soon as I closed Windows Live Sync Beta, my WiFi started working again shortly after. And this happened each time I tried to “back up” my music to another machine. I even tried it with a smaller folder—about a gig worth of music—and it happened again. Hopefully, this bug will be fixed with the official release of Windows Live Mesh, and at that time, I’d have to say that Mesh could be the winner in this category, since Dropbox doesn’t have an equivalent “unlimited” PC-to-PC syncing feature.  But until then, I can’t give out any kudos for an application that breaks my wireless Internet…

Storage Space – Advantage: Tie

Your Skydrive gives you a whopping 25 gigs of online storage—but for some reason, only 2 gigs of that is available for us by Windows Live Sync Beta. Beta users complained big time, so Microsoft threw us a bone and promised to up it to 5 gigs ones it comes out of beta. Dropbox gives you 2 gigs for free  and charges you extra if you want more—but  I may know of a groovy way to get 6 gigs of free additional Dropbox space for a total of 8 gigs, which nudges it into the lead.

Still, I’m calling this one a tie. Out of the box, both give you 2 gigs—but Mesh users can (or will) get 5 gigs without jumping through any hoops. Plus, that 25 gigs worth of space on the Skydrive sure looks cozy, and I’m betting that eventually, Microsoft will open it up for use via Mesh. Plus, that space is there for you to use through the web interface, if you really need it—with Dropbox, it’s 2 gigs no matter how you slice it that is unless you want a paid plan.. nahhh

Size – Advantage: Dropbox

In terms of memory usage, the Dropbox  (Dropbox.exe) process uses more than the Windows Live Sync Beta process (WLSync.exe). But Windows Live Sync Beta relies on MOE.exe as well, which is the Mesh Operating Environment. I know this for a fact because earlier, I had trouble with the Mesh Operating Environment crashing (re-install didn’t fix it—ended up reinstalling Windows 7), and when it did, Windows Live Sync Beta didn’t work. I suppose it makes sense—Windows Live Sync Beta as we know it is a combination of Live Sync and Mesh, after all.

Dropbox vs. Windows Live Sync Beta

The Little Things – Advantage: Dropbox

This is another category that might not be fair to declare a winner for, since Windows Live Sync Beta is a pre-release and Dropbox has been around for years. But I’m doing it anyway, and the winner is Dropbox. Dropbox just feels friendlier and less obtrusive overall. I appreciate the wee little blue logo next to the folder that reminds me which folders are being synced with Dropbox (as if I’d forget—its named “My Dropbox”). I like the system tray or Growl notifications that let me know when a file has been added or deleted. I like the “Recently changed files” menu on Dropbox. I like the ability to pause syncing and limit bandwidth (come to think of it, including such a feature in Live Sync Beta may have fixed my broken WiFi problem). Dropbox also allows proxies and Selective Sync (i.e. choose which folders within your Dropbox folder to sync).

I also like how Dropbox handles conflicted copies a little bit better. Both Dropbox and Window Live Sync Beta will avoid overwriting a file if its conflicted, and instead will give it a date, but Dropbox goes the extra mile and identifies the machine where the conflicted copy originated from. And I feel like the Dropbox system is a little bit more reliable, though it’s hard to get a file to conflict on purpose the same way it would in a real world situation. And if all goes to hell, you always have Undelete and Previous Versions to fall back on.

All those little things add up—and so far, Windows Live Sync Beta feels a bit lacking when it comes to features that make you go, “Oh, that’s kind of nice to have.”  Plus. with Dropbox, there’s a whole host of unofficial tips and tricks that let you do just about anything with the program—including syncing any folder on your PC with Dropbox (not just your Dropbox folder) and linking Dropbox to Microsoft Office.

Again, I really think that Windows Live Sync Beta (or Windows Live Mesh—whatever you want to call it for now) has some real potential. But Dropbox has a serious head start, and for now, I’m trusting my important files with them.



  1. Vadim

    September 1, 2010 at 7:54 am

    One point Live Sync : you can sync anything on your PC instead of stuff only in your ‘my dropbox’ folder.

  2. Robert

    September 1, 2010 at 1:37 pm

    What do you mean with: “Dropbox doesn’t handle remote connections”

    • Robert

      September 1, 2010 at 1:42 pm

      For some clarification: I have no idea what you mean with that.

      • MrGroove

        September 1, 2010 at 2:17 pm

        Microsoft Live Sync allows you to remote control another PC which is configured as a SYNC Partner. Basically it’s using the Microsoft Remote Desktop Protocol (RDP). Very handy if you need to remote control your PC at work or at home for a million different reasons. This of course only works if you want to remote control a Windows PC, not a MAC.

        Dropbox does not have this feature.

        Hope that helps.

        • Robert

          September 1, 2010 at 2:35 pm

          I understand. But why would you use this feature, if all that you want and need is in your dropbox? I mean, I scan all my stuff at work, the machine sends it to my email at work, I forward it with Sendto (like you reviewed) and its in my dropbox, where I can work with it with my Android phone. I mean, its in the dropbox, so why remotely enter you pc?

        • groovinJackman

          September 1, 2010 at 4:41 pm

          My thoughts exactly, Robert. That’s why I didn’t dock Dropbox any points for not having that feature.

          I imagine that you MIGHT need remote connection say, if you had Microsoft Publisher installed on your work computer but you didn’t buy a license for it at home. You could just log on to your work computer from home and use Publisher that way.

          But Dropbox’s lack of a VPN-like remote desktop feature doesn’t cause it to lose any luster in my eyes.

  3. TimO2020

    September 1, 2010 at 6:05 pm

    So what about Ive been backing up with them for over a year and it works great. Mozy vs. Dropbox?

  4. Robert

    September 1, 2010 at 10:06 pm

    Can you start programs from dropbox? Like you can start portable apps from a usb stick?

    • groovinJackman

      September 2, 2010 at 8:18 am

      I’ve never tried it, but that’s a good idea. From what I’ve read, it works well–as long as you remember to close out your portable apps on one machine and let it sync before opening it on another machine. I’ve heard people doing this successfully with Firefox and Thunderbird.

      • Robert

        September 2, 2010 at 8:27 am

        So, another reason why you dont need remote connections.

  5. Pacific

    September 20, 2010 at 12:51 pm

    Why are your posts double?
    Is it because the Dropbox or Live Sync has created an extra file?

    I found this site looking for a solution to a potential problem, and that is a doubling of my files. I don’t use Dropbox, just Windows Live Sync Version 2008 (tried the upgrade but didn’t complete it as I would have to re-set up my files all over).

    The extra files still show when I set my folder view option to “Do not show hidden files” or even “Do not show system files”
    What am I referring to here?

    My regular file would be named: file.doc
    And the extra file would have
    a hyphen,
    the email address (without the last letter) followed by
    a comma, and then the
    name of the computer, ending with
    the original type of file.

    Here is an example of the above file
    (original: file.doc)

    Is it possible to remove these ‘extra’ files, would they be reproduced again? Are they reference files?

    I want to remove them because when I go to publish changes to a website, these extra files are also published to the website, adding double (or more) of the space required.

    • MrGroove

      September 20, 2010 at 7:35 pm

      Sounds like something is REALLY wrong with your Windows Live Sync. I would uninstall and re-install. Something is for sure not right with the Sync. You should never get dupe files named after your computer…

      • Pacific

        September 20, 2010 at 11:34 pm

        Upon further investigation, I see that it is not the regular computer name that it is being used, but the computer name that I gave each computer in the Live Sync program.

        I have completed a Search through my whole computer, and removed the extra files, which were about 600 (after using Live Sync for 3/4 year.) Perhaps the problem is that I didn’t allow the 2nd computer to finish with copying the files over before shutting down. I have given it an extra hour this time, and will see what tomorrow brings., and report back.
        Good suggestion about re-installing; may resort to that.

        • Andytizer

          September 21, 2010 at 12:24 am

          You should try the new Live Sync Beta, it is much more feature rich and is better supported.

  6. DropMeshUser

    September 22, 2010 at 10:45 pm

    At home, we use Dropbox for our ‘important’ files, syncing them between our laptops and two of our desktops and in the cloud (in case, God forbid, the house burns down before we can get the ‘puters out). I totally agree with the comment that DB just ‘feels’ more robust for this.

    I like Live Mesh for the remote desktopping without dealing with persistent IP addys – I have a ‘media’ computer mostly filled with music files hooked up to the TV and sound system, and with LM I can sit on the couch or anywhere else and put on what I want to hear… I also like administering the desktops around the house from my laptop.

  7. Tim

    November 5, 2010 at 8:13 pm

    Late to the party, but thought I’d just say, I use DropBox and SkyDrive…but not Mesh.

    I use SkyDrive for the tight integration with Microsoft Office 2010, especially OneNote. Plus it also gives me the ability to view the files using Office Web App, if I’m somewhere without Office 2010 installed – neat.

    But DropBox is the storage sync king, and it just works with little fuss. Nice little sharing touches means you can share quickly without prerequisite accounts. And it’s cross platform, and has a neat web interface. Plus every file organiser/viewer on iOS seems to support DropBox.

  8. Larry

    April 25, 2011 at 9:25 am

    To my knowledge, the largest file that one can send to the windows cloud is 50Mb. So if you wish to transfer typical videos, you are SOOL, because they are much larger than 50Mb — even after they are condensed to .wmv size.

    I don’t know if there is a limit for the dropbox cloud, but I have sent to it 75-120Mb files with no issue whatsoever. They include videos that run as long as eight minutes each and zips that include a mix of 40 full-size .jpgs and wmvs.

    For this feature alone, I use dropbox. And the process is so simple, even an adult can get it working perfectly just a few seconds after reading the instructions.

    • Beyond_Life

      April 25, 2011 at 10:28 am

      The max size of a file in dropbox is 200 mb. To my knowlegde. If im wrong, please correct me.

  9. Larry

    April 25, 2011 at 11:23 am

    Clicking the “Reply” link on Beyond_Life’s comment just above did not work, so a new message it must be.

    DropBox is king of the file sizes. Here’s what I just found out about at their site:
    Files uploaded to Dropbox via the desktop application have no file size limit.
    Files uploaded through the website (by pressing the upload button) have a 300 MB cap. In other words, each file you upload through the website must be 300 MB or less.
    All files uploaded to your Dropbox must be smaller than the size of your Dropbox account’s storage quota. For example, if you have a free 2 GB account, you can upload one 2 GB file or many files that all add up to 2 GB. If you are over your storage quota, Dropbox will stop syncing until you are below your limit.

    • Beyond_Life

      April 25, 2011 at 11:29 am

      Ah ok, so I wrong hehe.

      But thats also the answer to a question I posted on the forum. This one:

      So, thanks for searching and providing me the answer.

      • Larry

        April 25, 2011 at 8:02 pm

        As for Beyond_Life’s other ?, the key to DropBox happiness is for both parties to delete files from their boxes after they have been downloaded. I don’t advise using DB for long-term storage; there are hard drives and other online services for that…some free or close to it.

        I ask people to notify me after they download the files, so I can then go to the DB site and execute a double deletion.

        All gone, full capacity restored.

        • MrGroove

          April 26, 2011 at 7:59 am

          Exactly. Kind of like sending a large email. After I send it, I usually go into my sent items and delete it. Dropbox space (and email server space) is precious. No need to hog it up with old files which have already been transferred.

  10. Pacific

    April 25, 2011 at 10:40 pm

    After being a Sync user for a few years, I have switched to CrashPlan for my backups, and love it. Simple, robust. I turned the speed of it way down while I am using the computer, but crank it up to 95% when i’m away. Bought 3 years worth of use. Never had one burp — yet!

    • MrGroove

      April 26, 2011 at 7:32 am

      That’s really good feedback Pacific – Crashplan is actually who I recommend now to family/friends/readers being that MOZY no longer runs with the Unlimited backup.

      How long did it take you to do your initial sync with them? Do you use their family plan with them?

  11. Wagner Silva

    July 16, 2011 at 1:13 am

    Cool sites!
    I really enjoyed the, that offers the pepedrive service. It offer 1Gb for free, you can upload any file having any size, and it is much easier than others sites.

  12. Tim Jefferson

    September 20, 2011 at 3:20 pm

    Incredibly illuminating bless you, I reckon your subscribers would most likely want far more information like this maintain the good effort.

  13. Randy

    December 30, 2011 at 2:25 pm

    I have Live Mesh 2011 and have the same issue you discribe in the paragraph titles “Backup FeaLive User Forum and get the answer that it must be my ISP.

    I have found that whenever I try to sync two computes that are both in my wifi network at the same time, my wireless crashes. If I turn off wifi on one and hook it to a wired port on my router, then things work fine.

    Have you learned of any ways to resolve this?

  14. Randy

    December 30, 2011 at 2:28 pm

    sorry – first paragraph scrambled…

    Same issue as your paragraph titled “Backup Features – Results Pending” I reported this on the Windows Live User forum and was told it must be my IPS

Leave a Reply

Your email address will not be published. Required fields are marked *


To Top