That dreaded syncing feeling: Will Microsoft EVER fix OneDrive?

Microsoft's long history of broken Windows sync


Microsoft and synchronisation go back a long way. Remember Briefcase, a feature of Windows 95 and later, which syncs files between two folders, one of which can be on a removable drive or on the network?

Briefcase was mostly replaced by offline network shares that synchronise local and server copies, a feature which remains in Windows today. Then there is SyncToy, a free tool that has not been updated since 2009, but which still has fans.

Synchronisation over the internet began with FolderShare, acquired with Byte Taxi in 2005, which evolved into Windows Live Sync and then Windows Live Mesh, Ray Ozzie’s pet project back in 2008 when he was Microsoft’s chief software architect. Ozzie was a sync specialist; he came to Microsoft from Groove Networks, also acquired by Microsoft in 2005, whose sync and collaboration product became Office Groove.

Look to the Sky(Drive)

Live Mesh was swept away by SkyDrive, Microsoft's cloud storage with a desktop synchronisation client, and SkyDrive was rebranded as OneDrive in February 2014. It is a key part of Microsoft’s cloud strategy, and ties in with Office Web Apps as well as iOS and (soon) Android versions of Office that use SkyDrive for storage.

Then again there is SkyDrive/OneDrive for Business, which has an entirely different ancestry, based on Microsoft’s document management and collaboration product SharePoint.

Users do not much enjoy opening documents from a web browser, so the SharePoint team also worked on synchronisation. They chose to adapt Groove, creating a product called Sharepoint WorkSpace 2010. Oddly, SharePoint WorkSpace did not integrate with Windows Explorer, but had its own Explorer-like user interface. It was also infuriating, with limitations on the number of documents and libraries that could be synced, and dependency on another utility called the Office Upload Center, which was prone to sulking and reporting upload errors that are hard to troubleshoot.

Microsoft revamped SharePoint WorkSpace for the Office 2013 wave of products. Integration with Windows Explorer replaced the old user interface, and it became the OneDrive for Business client for Office 365, Microsoft’s fast-growing suite of cloudy productivity applications.

Users of SharePoint online just have to click the Sync button in the browser view of their personal or team site, and OneDrive for Business springs into life, syncing online folders with offline copies. The OneDrive for Business client is still called Groove.exe though, suggesting that much of the old Groove remains.

With all this history, nobody could accuse Microsoft of lack of experience in synchronisation, and yet neither the consumer OneDrive client nor the OneDrive for Business client works as well as it should. Of the two, the consumer version is better, with its main foible (tamed somewhat in silent updates) a tendency to duplicate files if you access them from more than one device, appending the name of the device to each copy and making it difficult to work out which is more current.

Microsoft OneDrive

Hook, line and sync-er

OneDrive for Business, with its reassuring professional name, should be better but is not. Users set it up, everything goes well for a bit, and then messages appear about documents failing to sync. Office Upload Center typically complains about unresolved conflicts or a corrupt document cache. Unresolved conflicts are an issue with any synchronisation system, but puzzling when only one user ever modifies the document. Sync failures are perhaps the biggest frustration for Office 365 users and those who support them, and when it happens the usual advice is to delete and resync everything, with possible loss of recently changed files.

Some turn to an alternative approach to getting cloud files to show up in Windows Explorer, which is SharePoint’s implementation of the WebDAV (Web Distributed Authoring and Versioning) standard, accessed by clicking Open in Explorer in SharePoint online. It is better in some ways, worse in others. From time to time Windows refuses to show the files, showing an Access Denied message; there are a variety of fixes but this is no cure-all and works only online.

Smart, but with some snags

When Windows 8.1 was released, Microsoft introduced an innovation for consumer OneDrive. A feature called Smart Files was added to Windows, so that cloud files could appear in Windows Explorer without actually being downloaded, but are made available on demand. There is also an option to sync specific files or folders for offline use. It is a brilliant feature, especially for Ultrabooks or tablets like Surface which have relatively small SSDs.

Now that OneDrive storage limits are being lifted, syncing everything is not realistic on such devices.

The snag with this approach was that users did not understand Smart Files and hopped on a train thinking they could work on documents that were not really present. This prompted a change in the latest Windows 10 preview, explained by Microsoft’s Gabe Aul:

“Starting with this build, OneDrive will use selective sync. This means you choose what you want synced to your PC and it will be. What you see is really there and you don’t need to worry about downloading it.”

The solves one problem but has the side-effect of making any unsynced files invisible in Windows, the issue which Smart Files was invented to solve. When you try the latest Windows 10 on a tablet, it is soon apparent that the old system was better, confusion or no. Power users agreed, and protested.

Microsoft’s Jason Moore responded, giving some clues about the future of OneDrive:

“We didn’t just “turn off” placeholders – we’re making fundamental improvements to how Sync works, focusing on reliability in all scenarios, bringing together OneDrive and OneDrive for Business in one sync engine, and making sure we have a model that can scale to unlimited storage. In Windows 10, that means we’ll use selective sync instead of placeholders. But we’re adding additional capabilities, so the experience you get in Windows 10 build 9879 is just the beginning. For instance, you’ll be able to search all of your files on OneDrive – even those that aren’t sync’ed to your PC – and access those files directly from the search results. And we’ll solve for the scenario of having a large photo collection in the cloud but limited disk space on your PC.”

If that “one sync engine” is better than either of the current ones, Windows users will be greatly relieved. ®

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