If an HTTP Error 500 occurs when using links in email messages from Project Insight, but the configuration of IIS is set in accordance with the installation instructions to use a URL for 404 pages, it could be that the following command was not run in accordance with the Project Insight installation instructions.
%windir%\system32\inetsrv\appcmd.exe unlock config -section:system.webServer/security/requestFiltering
To fix the problem, run the command and try the link again. You may have to reset IIS, but you may want to try it first without a reset if users are currently on the system.
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