Testing with IE perhaps is going i think is a ticket open, the other way you upload Files via a php fileuploader and then you must set chmod 777 , in the silverstripe you must go to files and first view the files in sst filemanager, then you can see and put in your site in the browser!!!
Open in the sst the filemanager and view are the files are there???
then you can get in the sst site , you must have installed the http://www.silverstripe.com/modules/ Gallery (v0.2.2)
1. dont forget the /db/build/?flush=1 and the /?flush=1
then you become a folder for the Gallery put the pictures in there and create a Gallery Site in the sst!!!
Fine in the Tab Extensions on the gallery Site klicking the first --- png,jpg,jpeg,gif.. perhaps delete your created extension Save all und View your Gallery!!! I think its now going these point is at my site these way..