Jeremy, I found your old message with this title. I struck the same thing, where the current drive wasn''t the same as the drive I wanted to serve (some) files from. So here''s the patch to add to lib/mongrel/handlers.rb contains class DirHandler. I added two things, first to initialize: def initialize(path, listing_allowed=true, index_html="index.html") @abs = path == "/" # Absolute paths are allowed @path = File.expand_path(path) ... next to method can_serve, which should start with this: def can_serve(path_info) req_path = HttpRequest.unescape(path_info) # Add path prefix, except to absolute Windows paths: req_path = File.join(@path,req_path) if (!@abs || req_path =~ % r{\a[A-Z]:[/^\\]}i) # Expand it to an absolute path: req_path = File.expand_path req_path if File.exist? req_path .... Essentially this says if absolute paths are allowed and path_info has a drive letter, don''t add the initial path. This should get into an official mongrel release sometime... Clifford Heath, Data Constellation.