WEBrick+Windowsでサービスしているところはあまり無いと思いますがファイルを不正に読み取られる可能性があります。
CVE-2008-1891
Overview
Directory traversal vulnerability in WEBrick in Ruby 1.9.0 and earlier, when using NTFS or FAT filesystems, allows remote attackers to read arbitrary CGI files via a trailing (1) + (plus), (2) %2b (encoded plus), (3) . (dot), (4) %2e (encoded dot), or (5) %20 (encoded space) character in the URI, possibly related to the WEBrick::HTTPServlet::FileHandler and WEBrick::HTTPServer.new functionality and the :DocumentRoot option.
Impact
CVSS Severity (version 2.0):
CVSS v2 Base score: 5.0 (Medium) (AV:N/AC:L/Au:N/C:P/I:N/A:N) (legend)
Impact Subscore: 2.9
Exploitability Subscore: 10.0Access Vector: Network exploitable
Access Complexity: Low
Authentication: Not required to exploit
Impact Type: Allows unauthorized disclosure of information
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