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I have a bunch of Office documents sitting on my harddrive. I would like to upload them all to my Skydrive account. Is there an automated way to do this?

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Another workaround is to compress all files using a compression tool and upload the single file – Sathya Sep 18 '10 at 15:43
@Sathya: the problem is, you can't uncompress the files in Skyrive and actually edit or look at them if you wanted to access them via Office Web Apps (built into Skydrive)....just a thought. – studiohack Sep 18 '10 at 18:35

Gladinet Cloud Storage can do this, they have a free version that lets you access several cloud storage services (including sky drive) as if it where local.

Storage Supported

Amazon S3
AT&T Synaptic Storage
EMC Atmos Online
File Server Share
Google Docs
Google Storage
Peer1 CloudOne
Windows Live SkyDrive
Windows Azure
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>.< beaten by 2 minutes – Sathya Sep 18 '10 at 15:36
If Gladinet supported Dropbox too, I would be happy. :P – studiohack Sep 18 '10 at 15:43
@studiohack: But Dropbox already is an easy to use GUI drag and drop application. I can't see how Gladinet could change anything for the better. – paradroid Sep 18 '10 at 15:51
@jason404: I agree with you, their interface is awesome already...just thought it would be cool to have it rolled all in one...full disclosure: i have never used Gladinet... – studiohack Sep 18 '10 at 15:54

You can drag and drop multiple files through the Skydrive website if you have Microsoft Silverlight installed.

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beware that the Silverlight upload tool does not work well in Firefox 3.6...use Internet Explorer for that... – studiohack Sep 18 '10 at 15:37
Never use Firefox, but it seems to work well with Chrome – nateify Sep 18 '10 at 15:42

Check out SDExplorer.

SDExplorer is a free, easy-to-use, but very powerful extension for Windows Explorer. With SDExplorer you can perform all everyday operations with your documents on Microsoft Live SkyDrive™ using Windows Explorer, as if they were on your computer itself. Moreover, you don't need to install and configure any additional programs or ActiveX components. SDExplorer will take care of communicating with the online storage all by itself.

Why do you need SDExplorer:

* If you want to make your work with SkyDrive™ more efficient;
* If you are tired of the inconvenient and complex web interface for Microsoft Live SkyDrive™.
* If you want to assign a drive letter to your SkyDrive™ folders;
* If you want to work with your cloud storage files quickly;
* If you want the data on your SkyDrive™ account to always be at your fingertips.
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+1 I switched from Gladinet to this a few months ago. I recommend the Pro version, which is very cheap, as it adds several useful features. – paradroid Sep 18 '10 at 15:52

Now you don't need any third party tools. Just use the standard SkyDrive client from Microsoft.

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For others reading along: the standard client won't run on XP. The OP asked for Win7 so this is fine. – Jan Doggen Jun 14 '13 at 11:49
As an alternative you could use syncdriver app or all others mentioned above. – Oleg S Jul 1 '13 at 11:44

Automate the task with the iMacros for IE/Firefox browser macro recorder. I automte my Flickr uploads with it.

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you would have to choose your files and which folder and such, and then would have to change your recording every once in a while, depending on what you want to do... – studiohack Sep 18 '10 at 18:34

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