Email Header Finger Printing

When we send an Email, the SMTP server creates a header.Study of the Mail server name reveals the OS of the server. For all this ,we have to analyze the Email Header first. The email header reveals a lot of other sensitive information about the sender including his IP.We will discuss more on this topic on other posts.
Countermeasures :
Change the mail daemon settings 

A sample Email header is shown below :

Delivered-To:XXX @gmail.com
Received: by 10.142.100.4 with SMTP id x4cs39161wfb;
        Tue, 17 Nov 2009 22:37:56 -0800 (PST)
Received: by 10.90.17.29 with SMTP id 29mr1540839agq.79.1258526174775;
        Tue, 17 Nov 2009 22:36:14 -0800 (PST)
Return-Path: 
Received: from mail15-a-ac.linkedin.com (mail15-a-ac.linkedin.com [208.111.169.137])
        by mx.google.com with ESMTP id 30si16545010iwn.121.2009.11.17.22.36.13;
        Tue, 17 Nov 2009 22:36:13 -0800 (PST)
Received-SPF: pass (google.com: domain of s-qKShvR1E_bKJbE3KpcihvgYpqS5pjeiVFRKjniEn-5Sp4jYEI5tJj_@bounce.linkedin.com designates 208.111.169.137 as permitted sender) client-ip=208.111.169.137;
Authentication-Results: mx.google.com; spf=pass (google.com: domain of s-qKShvR1E_bKJbE3KpcihvgYpqS5pjeiVFRKjniEn-5Sp4jYEI5tJj_@bounce.linkedin.com designates 208.111.169.137 as permitted sender) smtp.mail=s-qKShvR1E_bKJbE3KpcihvgYpqS5pjeiVFRKjniEn-5Sp4jYEI5tJj_@bounce.linkedin.com; dkim=pass header.i=communication@linkedin.com
DomainKey-Signature: s=prod; d=linkedin.com; c=nofws; q=dns;
  h=Sender:Date:From:To:Message-ID:Subject:MIME-Version:
   Content-Type:X-LinkedIn-fbl;
  b=LAlAw9S8qrGPLt6phtZNvQ37jeg3yvtYlApfNHApbwizFBIvNvk2D1H6
   r7PxLyDTGK5YmRBn84TgBPD5FB0gt90r9Khp4TnNFIHyM3Sy64uMytmRj
   N4agg6dfvT5H2mO;
DKIM-Signature: v=1; a=rsa-sha256; c=simple/simple;
  d=linkedin.com; i=communication@linkedin.com; q=dns/txt;
  s=proddkim; t=1258526173; x=1290062173;
  h=from:sender:reply-to:subject:date:message-id:to:cc:
   mime-version:content-transfer-encoding:content-id:
   content-description:resent-date:resent-from:resent-sender:
   resent-to:resent-cc:resent-message-id:in-reply-to:
   references:list-id:list-help:list-unsubscribe:
   list-subscribe:list-post:list-owner:list-archive;
  z=From:=20LinkedIn=20Communication=20
   in.com>|Sender:=20messages-noreply@bounce.linkedin.com
   |Subject:=20LinkedIn=20Messages,=2011/17/2009|Date:=20Tue
   ,=2017=20Nov=202009=2022:36:03=20-0800=20(PST)
   |Message-ID:=20<2138821644.368566.1258526163419.JavaMail.
   app@ech3-cdn09.prod>|To:=20"Mr.Swaroop=20Krishnan=20S"=20
   |MIME-Version:=201.0;
  bh=HFHniqCRWqBOKiU6PXUVuudYIJ3jsx+QLmyfTd3eFzU=;
  b=SDfsYwsz/HCedRw3aFZ2JkOkKrLzzK2R1gVWv2WDNXhKtr2kM0ioAlZi
   m230bpQm4ZzCi2fwM2yyYbY8GauwKPZav6r23wyGA4hTBwHKLheSmXFI5
   /+urlA2oJGJPlWR;
Sender: messages-noreply@bounce.linkedin.com
Date: Tue, 17 Nov 2009 22:36:03 -0800 (PST)
From: LinkedIn Communication 
To: "Mr.Swaroop Krishnan S" 
Message-ID: <2138821644.368566.1258526163419.JavaMail.app@ech3-cdn09.prod>
Subject: LinkedIn Messages, 11/17/2009
MIME-Version: 1.0
Content-Type: multipart/alternative; 
 boundary="----=_Part_368565_1338859.1258526163416"
X-LinkedIn-fbl: qKShvR1E_bKJbE3KpcihvgYpqS5pjeiVFRKjniEn-5Sp4jYEI5tJj_

------=_Part_368565_1338859.1258526163416
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 7bit

OS Fingerprinting -Finding Remote Host's OS

 It is very important for an attacker to know about the OS of the target.Different OS's have different stacks and kernels.The response to same message is different in different OS's so by analyzing these messages we can know about the OS in the host.Attacker sends packets made using the packet generation softwares and the target is forced to respond to it.Thus OS finger printing is done.

The techniques used for this purpose can be classified in to 2 types namely :

1) Active finger printing
2) Passive finger printing

Active fingerprinting :
steps:
A customized data packet is send to the target host.
The response generated is recorded using  the packet sniffer.
The recorded response is studied and compared to known responses and OS is identified.

Fators helping us to identify the OS :

TCP initial window size of the packets.
ACK values of the packets.
Initial Sequence Number(ISN)  values
Heading of overlapped fragments.
ICMP Message quoting method
ICMP Error Message quenching method
ICMP Error Message Echoing integrity

Problem:
The attacker will have to send the packets actively to the target and record its responses.
This method is not anonymous.So it may have tha attacker caught in the act.

That is why we go for Passive Fingerprinting.

TOOLS for active finger printing :

Nmap
Quso
Aping


Passive Fingerprinting :
This method is  anonymous. It is very difficult to identify passive fingerprinting.

The main steps in this method are as  follows :
The attacker uses a sniffer to record the data packets sent by the target.
The various parts of the response is analyzed for particular values which are specific for a particular OS.
Thus the OS of host is found out.The attacker may install the sniffer in a cafe and analyze the packets recieved while someone connects to the same computer.

The main fields studied in the passive method are:
TTL value
The window size
Don't fragment bit
Type of source (TOS)

 Consider the example :
When we recieve a
windows size =9000
TOS =0
DFB =yes
then the host must be running a Win9X or Win NT

Countermeasures:

Change the default values of the parameters studied.
Mislead the attacker by giving values of another OS.
Use ACL for filtering.