Some research turned up this Stack Overflow question, the top answer of which led me to the solution. Evidently, the error redirection feature in IIS requires a Windows feature, specifically Internet Information Services → World Wide Web Services → Common HTTP Features → HTTP Errors, which in some cases does not get enabled by default.
My site is actually hosted on a Windows Server 2008 machine, so the Windows Features dialog doesn't exist. The feature in question is a Role Service of the IIS (Web Server) role.
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