After making the changes explained here I was able to upload larger files due to the IIS connection timing out. However, I ran into a similar problem a few days ago when trying to upload a 30 MB file to a Document Library and the previous solution didn’t seem to help.
My research eventually brought me to this Knowledge Base article. It seems that IIS 7 on Windows Server 2008 has a file size limit of 28 MB.
I’m sure Microsoft had a really good reason for adding these limits to their newest web server but I have been unable to find one. Would it be too much to ask for the SharePoint configuration tools to make these changes when it is creating the new site in the first place?
So I added the following to the web.config file in the virtual server folder and all was well:
I had to add it to the end of the file (just before the </configuration> tag). Adding it to the beginning of the file caused an “Internal Server Error”.