DouglasPHill,
You should avoid using the relative path.
Please using the following methods:
//use the app-based path
Editor1.ImageGalleryPath="~/uploads";
//use the absolute path
Editor1.ImageGalleryPath="/uploads";
In the version 4.0, you can use the physical path:
//use the physical path Editor1.Setting["security:ImageGalleryPath"]= @"c:\inetpub\wwwroot\uploads";
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