While testing a web application, does it give you debugging information? Does it present a stack trace? Or does it give you a generic error message? That is what that check is looking for. Sometimes web applications leave debug set to true when they get moved to production. The result is that a user is given the stack trace when an error is encountered rather than a generic error message. That stack trace can indicate the technologies or other information about what the application is running on that should not be disclosed.
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