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Uploading large files after migration leads to intermittent 500 server error timeouts

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Hey everyone!

I recently migrated a site from Server 2003 + IIS6 to Server 2008 R2 + IIS7. At this site, users log in and upload different kinds of documents to the site, ranging from 5mb to 30mb. Most users are not experiencing any issues, however a few of our users are getting500 Internal server error when trying to upload a 22MB file to the site. I have used the exact same file and used every browser to attempt to recreate the issue and am unable to do so. I have worked with a few other users that are remote and they are also no thaving errors. A couple of the users however are getting this error sometimes on large files.

What do you guys think?


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