When I try to upload an attachment that is greater than about 30MB, I get a 404 at the 98% upload mark. Has anyone else seen this? I've tried attachments of sizes from very small (a few k) to over 40MB, and every time one of them is larger than 30MB, it fails in this manner with the browser redirecting to a 404 error page.
My attachment file size limit is set to 200MB, connection timeouts are turned off (set to 0, which makes them essentially infinite), and I have set the upload attachments to use the file system rather than storing in the database.
I ran in to the same issue and was thrilled to see this answer since I'd been scratching my head on this one for most of the afternoon. However, there is no mention of an actual fix for the problem at hand. Not complaining, just wanting to help. In IIS 7.5, you can update the value for file uploads to be up to 2 GB by opening the IIS Manager, selecting the IIS Server and double clicking the "Configuration Editor" in the bottom section.
Once this opens, in the section drop down, you'll want to navigate to the system.webServer/security/requestFiltering section of the config. Expand the requestLimits sub-item and then update the maxAllowedContentLength value to whatever is appropriate.
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