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First off, I'm on a Windows 2008 box running IIS7 with a web.config file not htaccess.

That being said, I've migrated my old Apache(XAMPP) installed WPMS site over to a new IIS7 server successfully with one glitch: my media files are doing some really funky stuff.

// The run down:
I have my main site and about 200+ subsites. Uploading new files to the blogs.dir folder is successful and I'm able to see them on my site just fine afterwards.

// The funk:
SOME of my old files (PDF and Word documents) on my main site are still linked properly. It seems to be only pre-move image files that are affected. The files are still listed in the media library correctly and I can see the files in the directories themselves, but there is a disconnect between the Library and the directories.

Caveat: I've had to keep my main site's upload folder set to /wp-content/blogs.dir/1/files/ because my WordPress installation was pre-3.0. This hasn't shown itself to be an issue yet, since I can still see some of the files and I can upload new files. I tried moving it to /wp-content/uploads/, but that seemed to give me more of a headache.

Here is my web.config file in case someone is able to see some issue within it that's causing the problem.

Any help would be greatly appreciated!

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I figured it out. Here's the wordpress.org forum thread of me working through it.

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