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Could you summarize (you can send it in a new private conversation if you want) where the files that *weren't* migrated were located relative to your CS2007 installation?

I'd like to determine why the upgrade tool didn't get all of your files migrated.

Just wanted to let you know that I solved the problem. It was caused by UrlScan filter not liking dots in the file name. Since CS2008 is using cfs-file.ashx/__key/CommunityServer.Components.Avatars/00.00.00.21.28/avatar.jpg type of path, the dots were causing UrlScan to "block" the request.

Solution: Change UrlScan.ini to allow dots in path.

We had the same problem. cfs-file.ashx wasn't serving images, even though they'd uploaded properly. When we checked the urlscan log file we found all the image requests blocked. A change to the AllowDotInPath setting in urlscan.ini and restart iis and everything was good.