If you’ve set up the Outlook Hotmail Connector to sync your contact and appointment data to your Windows Live account, and then sync this information to your windows phone, you’ve probably noticed that pictures that were included with your Outlook contacts did not sync to Windows Live.

Windows Live accommodates photos with contacts, but the only contacts you'll see in your Windows Live Contacts that have photos are your Live Messenger contacts who have also posted a picture of themselves to their Windows Live account.

You'll need to manually restore the photographs to your contacts on the phone.

The easiest way to restore your contact pictures to your windows phone is to upload the pictures to your Windows Live account and then sync the pictures over to your phone.

Upload the Pictures to your Windows Live Account

• Gather together all your contact photos and place them in a folder on your computer
• Then, using Internet Explorer, login to your Windows Live account > go to Photos > Select the Mobile photos album > Create folder > input "Contact Photos" in the space provided (or whatever you prefer to call the album) > Next
• Open up File Explorer in a new window on your computer, navigate to your contacts folder and select all the contacts. 
• Drag all of the pictures to the "Drop photos here or select photos form your computer" box in Windows Live (the drag option will only work if you are using Internet Explorer)

Sync the Pictures to your Phone

• On your phone, open up the Pictures hub > tap all >  now you'll see a "Contact pictures from Windows Live" album.  Open up the Contact pictures album and tap each picture to download it from your Windows Live account, then tap the three periods in the lower right hand corner of the screen and tap "Save to Phone"
• Go to the people hub
• Select a contact that you want to add a picture to and tap the pencil icon 
• Tap "add photo" and then select the picture from your Saved Pictures.

When you sync your phone to Windows Live, the pictures will also sync to Windows Live.  You won’t see the pictures there, but if you get another phone and sync to your Windows Live account, the pictures will be synced over to your new windows phone.