A lot of people have more than one computer that they use on a regular basis and in most cases that is usually a combination of a desktop and laptop device.

That is exactly the setup my wife uses and the laptop comes in very handy because she likes working on our lanai which is open to the outdoors but screened in to keep the massive Florida mosquitoes away.

It used to be that I had to manually sync both her Outlook PST file and her documents each time before she would go remote on the laptop to work as she liked to be able to check her mail and work on her latest project.  This of course became very challenging because if I was not around then she was unable to update the laptop to have her latest data. This meant she was resigned to working in the home office on her desktop.

So it was about this time that Windows Live Sync appeared and it allowed me to sync those key documents folders to her laptop but it would not sync the PST file. This was by design because of the issues you can run into with networked PST files for Outlook.

So we solved the PST sync issue by moving our email away from POP3 accounts and to Office 365 while also maintaining our Hotmail.com, now known as Outlook.com, accounts.  That meant Outlook would maintain a locally cached copy of our email inboxes and folders on each device yet still store the data on the server.  So anytime we went to the other device and used Outlook to access our email there would be a short syncing of data to get everything up to date.  That meant no PST moves were required to be up to date on each device.  This strategy also worked well with access to our email on the Windows Phones we use.

Then came the time that Windows Live Sync was being phased out for a new service called SkyDrive.  SkyDrive was a definite enhancement to what Windows Live Sync offered but it removed a very popular feature. That feature, being able to sync any folder anywhere on your system, was gone and now all SkyDrive folders would appear under one main directory, SkyDrive, in a user directory of files.

Now SkyDrive continued to perform well and keep files in sync between my wife’s desktop and laptop but no longer could I directly sync those folders in their own locations.

However, Windows has a nifty feature on the My Documents and My Pictures system folders that let you move them to a new target or location.  When you make that change, which I will show you how to do later in this post, Windows will also display all of your documents and photos in the system folders for each as if they were really in those folders.

Basically, the appearance of the files in the system folders is transparent to the actual location of the files which in this case is the SkyDrive folder in your user directory.  You just access your files in the My Documents and My Pictures directories as normal. Plus this is compatible with all your software as well for file locations, etc.

So on to the how-to portion of this post.

First you must install the SkyDrive App for your computer and you do that by visiting SkyDrive.com and logging in with your Microsoft Account.

In the lower left corner of the screen you will see the size of your SkyDrive storage and a few menu choices. Select Get SkyDrive apps.


That will take you to the SkyDrive App download page. It will automatically detect your OS information and give you a download link.


Accept the defaults for this installation and it will grab your SkyDrive files from the cloud and store them on your local computer in the SkyDrive directory in your user files.


The green check mark on each folder in your SkyDrive directory indicates that it is in sync with the cloud.  It will show a refresh icon if it is in the process of synching data.

Now the next step is to tell your system to relocate your My Documents and My Pictures directories to their equivalents in the SkyDrive folder.

The first step is to open up your user directories. This is normally located on your desktop.


Next Right Click on the directory you want to move, in this case My Documents, and select Properties.


That will bring up this dialog box and you need to select the Location tab.


Now click the Move button in the center of the dialog box.


A Windows Explorer window will open up and all you need to do is browse to the SkyDrive folder which is usually on the bottom of the list in the upper left hand corner of the window and then select the Documents directory and then click Select Folder. You will get prompted to confirm you want to move everything from your current My Documents folder to the new location – just answer yes.

Repeat these steps and just replace the target folder you want to move such as My Pictures to Pictures.

Once you are all done with these steps then you must go to your other computer and repeat this process, including installing SkyDrive if it is not already there, and then moving your My Documents and My Pictures as noted above.

Just a couple of notes on this process:

  • The Documents and Pictures directories on SkyDrive will get renamed to My Documents and My Pictures on SkyDrive. Do not be alarmed as this is normal behavior.
  • Be aware of the size of your directories on your local computer. If they exceed the total amount of storage that you have in the cloud on SkyDrive then this will not work out so well.  There is an option to select the specific folders you want to sync with SkyDrive to help you manage this. Just go to the settings for SkyDrive and then select the Choose Folders tab. You can also do this during the installation of SkyDrive and its setup.  Just be aware that not all of your files will be synched on both sides in this case so you will want to make sure you sync the most important files you need on both devices.
  • You can do this with your other system folders like My Videos, My Podcasts and My Music. However, I will refer you back to the previous item about the size of those directories and its impact on synching everything.
  • This will not work on a device like the Microsoft Surface RT as it does not store your SkyDrive files on the local device.

Hopefully, this will help you take full advantage of the ability to store files in SkyDrive and have them accessible on multiple devices and keeping everything in sync.

If you have any questions please let me know.