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I'm creating a theme for a particular WordPress site. There's one spot in the sidebar that displays a photo. The user might want to change the photo once a week. He doesn't want to use FTP to upload the new photo, or edit any theme files.

How can I set up the theme so he can upload a photo from within WordPress, e.g. to the media library, and have it replace the photo in the sidebar?

The only thing I can think of is to have him upload the photo to the Media Library, click the hidden 'Edit' link under the photo in the media library, select and copy the file URL, then go to Appearance > Widgets and paste the URL into a widget that displays the photo. But this seems like a lot to ask of a non-technical user, and there's a lot that can go wrong. Is there a better way?

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I ran into a similar problem recently. I found plug-in called "image widget" http://wordpress.org/extend/plugins/image-widget/screenshots/ that enabled upload right in the widget.

The client though had no idea how to barely log in and find the widgets so I ended up using a flickr widget since it was more user friendly ( aka they could upload the image from their iphone to flickr).

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