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1
Securing Email Communications
Simplifying Security.
Module 9
Copyright © by EC-Council
All Rights Reserved. Reproduction is Strictly Prohibited.
2
Individuals who are concerned about data loss may be surprised to hear of the number of 
hacking attacks attempted on the Treasury.
Chancellor George Osborne revealed at the Google Zeitgeist conference on Monday (May 
16th) that each month around 20,000 malicious emails are sent to UK government networks.
Furthermore, he noted: "During 2010, hostile intelligence agencies made hundreds of serious 
and pre‐planned attempts to break into the Treasury's computer system. In fact, it averaged 
out as more than one attempt per day."
As a result of these figures, Mr Osborne pointed out that the Treasury is one of the most 
targeted by data attacks across the whole of Whitehall.
Government is not the only area concerned about breaches though, with Square Enix recently 
confirming that a couple of websites it is associated with have been attacked.
Email Security: Malicious
Messages 'A Problem For Govt.Too'
May 16, 2011
http://www.cryptzone.com
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3
Module Objectives
Email System
Email Security
Email Security Threats
Spamming
Hoax/Chain and Scam Emails
Email Security Control Layers
Email Security Procedures
How to Obtain Digital Certificates?
Online Email Encryption Service
Email Security Tools
Email Security Checklist
Security Checklist for Checking Emails 
on Mobile
Copyright © by EC-Council
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4
Module Flow
Introduction to
Email Security
Email
Security Threats
Email
Security Procedures
How to Obtain
Digital Certificates?
Email
Security Tools
Copyright © by EC-Council
All Rights Reserved. Reproduction is Strictly Prohibited.
5
Email Threat Scenario 2011
Email Spam Intercepted
Top 5 Geographies
Global Spam Rate (89.1%)
Italy
Denmark
Austria
France
Switzerland
93.5%
93.2% 
92.0% 
92.0% 
91.5% 
Email Virus Intercepted
Top 5 Geographies
Global Virus Rate (1 in 284.2)
South Africa
UK
Spain
Oman
Switzerland
1 in 147.2
1 in 164.6
1 in 174.1
1 in 229.0
1 in 237.8
Email Phish Intercepted
Top 5 Geographies
Global Phish Rate (1 in 444.5)
South Africa
UK
Oman
United 
Arab 
Emirates
New Zealand
1 in 99.0
1 in 214.8
1 in 341.9
1 in 424.0
1 in 568.1
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6
HowVarious Email SystemsWork?
Email (electronic mail) is a method of exchanging digital messages from a sender to one or 
more recipients
Companies such as Microsoft, Yahoo!, Google, and AOL offer free email accounts
Email accounts can be accessed from any web browser or a standalone email client such as 
Microsoft Outlook, Mozilla Thunderbird, etc.
Internet
Email Clients Email ClientsEmail Server Email ServerSender Receiver
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7
Email Security
No email communication is 100% secure
Insecure emails allow attackers to intercept personal and 
sensitive information of the user
If not secured, emails sent/received can be forged or 
read by others
Emails are one of the sources of viruses and various 
malicious programs
It is necessary to secure emails to have safer communications 
and to protect privacy
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8
Module Flow
Introduction to
Email Security
Email
Security Threats
Email
Security Procedures
How to Obtain
Digital Certificates?
Email
Security Tools
Copyright © by EC-Council
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9
Email Security Threats
Phishing mails lure victims to provide 
personal data
Attachments may contain a virus, Trojan, worms,  
keylogger, etc., and opening such attachments 
infects the computer
The user may receive spam mails
may contain malware allowing 
attackers to take control of the 
user computer
The user may receive hoax emails
that contain false information 
telling him/her to forward the 
mail
Mails may contain links that 
websites hosting malwares 
and pornographic material
Malicious Email Attachments
Malicious User Redirection
Hoax/Chain Mail
Phishing
Spamming
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10
Malicious Email Attachments
 Email attachments are major email security threats as they offers attackers 
easiest and most powerful ways to attack a PC
 Most malicious attachments install a virus, Trojan, spyware or any other kind of 
malware code as soon as you open them
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11
Email Attachments: Caution
Check if the email was ever 
received from the source
Save and scan all email 
attachments before opening them
Check if the subject line and name 
of the attachment are correlated 
with each other  
Check if the email is from one of 
your contacts
Never open an email attachment
from unreliable sources
Do not open attachments with 
suspicious or unknown file
extensions
Example: *.exe, *.vbs,*.bat,*.ini, 
*.bin, *.com, *.pif, *.zzx
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12
Spamming
 Spamming is the use of email 
systems to send unsolicited bulk 
messages indiscriminately 
overloading the users’ inbox
 Spam emails may contain malicious 
computer programs such as viruses 
and Trojans
 According to Symantec, spam 
makes up 89.1 % of all email traffic 
0 20 40 60%
3%
7%
8%
18%
27%
44%
Oceania
North America
Africa
South America
Asia
Europe
http://www.m86security.com
Spam Sources by Continent
Unsolicited bulk messages 
Attacker User
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13
Avoid opening spam messages 
(classified by spam filters)
Use the email client's 
spam filter and anti‐
spamming tools
Never follow the links in spam 
messages
Report suspicious email as 
spam
Do not use official 
email address while 
registering with any 
website
Use a different email address when 
posting messages to any public 
forum
Spamming Countermeasures
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14
Anti-Spamming Tool: SPAMfighter
http://www.spamfighter.com
SPAMfighter protects all the email accounts on a PC against "phishing", identity theft, 
and other email frauds
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15
Hoax/Chain and Scam Emails
 Hoaxes are email messages warning the 
recipients of non‐existent threats
 Users are also warned of adverse effects 
if they do not forward the email to others
 A scam email asks for personal information 
such as bank account details, credit card 
numbers, password, etc.
 The sender of scam mails may also ask the 
recipient to forward the email to everyone in 
his/her contact list
http://www.scamletters.com
http://diamond‐back.com
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1616
Nigerian Scam
A Nigerian scam is a form of advance 
payment  of money or money transfer
This scam is called a Nigerian scam 
because initially it started from Nigeria, 
but they can come in anywhere in the 
world
Using this scam, scammers contact you 
by sending an email and offer you a 
share in a large sum of money
They say they want to transfer money, 
which was trapped in banks during civil 
wars, to your account
They may also cite various reasons such 
as massive inheritance problems, 
government restrictions, or taxes in the 
scammer’s country
Scammers ask you to pay money or give 
them your bank account details to help 
them transfer the money
From: Mr. Wong Du
Seoul, South Korea.
I will introduce myself I am Mr.Wong du a Banker working in a bank in south Korea Until now I am 
the account officer to most of the south Korea government accounts and I have since discovered 
that most of the account are dormant account with a lot of money in the account on further 
investigation I found out that one particular account belong to the former president of south Korean 
MR PARK CHUNG HEE, who ruled south Korean from 1963‐1979 and this particular account has a 
deposit of $48m with no next of kin.
My proposal is that since I am the account officer and the money or the account is dormant and 
there is no next of kin obviously the account owner the former president of South Korea has died 
long time ago, that you should provide an account for the money to be transferred.
The money that is floating in the bank right now is $48m and this is what I want to transfer to your 
account for our mutual benefit.
Please if this is okay by you I will advice that you contact me through my direct email address.
Please this transaction should be kept confidential. For your assistance as the account owner we 
shall share the money on equal basis.
Your reply will be appreciated,
Thank you.
Wong Du
http://in.mail.yahoo.com/
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17
Module Flow
Introduction to
Email Security
Email
Security Threats
Email
Security Procedures
How to Obtain
Digital Certificates?
Email
Security Tools
Copyright © by EC-Council
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18
Email Security
Control Layers
Sender
Receiver
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19
Email Security Procedures
Create and use strong 
passwords
Use HTTPS for browser 
connection
Disable/unselect Keep Me 
Signed In/Remember Me 
functions
Scan email attachments 
for malware
Create junk email filter 
in email clients
Avoid unwanted emails 
using filters 
Digitally sign your mail 
messages  
Turn off the preview  
feature and change  
download settings in 
email clients 
Provide alternate email 
address for mail 
recovery
Check for last logging 
activity
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20
Creating Strong Passwords
Strong passwords are difficult to crack or guess
A strong password can be created by using combinations of numbers (0‐9), letters 
in upper and lower case (a‐z and A‐Z), and special characters (!@#$% …)
Create a strong but easy to remember password and do not write it anywhere 
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21
Alternate Email Address
An alternate email address is the additional email address required at signup for most of 
the free email services such as Gmail and Yahoo
It is used by service providers to verify the account creator’s identify 
Alternate email addresses are used for password recovery in case  you forgot the password
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22
Keep Me Signed In/Remember Me
Most of the popular email clients 
have the Keep me signed in or 
Remember Me options
Checking these options allow the 
email client to fetch the email inbox 
of the user without him/her having 
to fill in the login details again 
This allows other users to access the 
user’s email
Users should check that this option 
is not selected when accessing 
email from a public computer
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23
Using HTTPS
 Web mails such as Gmail, Yahoomail, Hotmail, AOL Mail, etc. have an option for choosing the 
communication protocol for browser connection 
 Change the Browser connection setting to receive email using HTTPS (HTTPSecure)
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24
Check for Last Account Activity
Always check the latest email account activity 
if the feature is available with the email 
service
Latest account activity includes information 
such as access type (browser, mobile, POP3, 
etc.), location (IP address), and date/time of 
account activities
To check account activity in Gmail, scroll to the 
bottom of the page and click Details 
Immediately change your password and 
password hints if you observe any suspicious 
activity
Copyright © by EC-Council
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25
Be cautious when opening any email attachment
Save all the attachments and scan them properly for malware using an antivirus 
before opening
Enable the antivirus to automatically scan all the emails and downloads
Scanning Email Attachments
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26
Turn Off Preview Feature
Email clients have an option to show a preview of 
the email
Turn off this feature in email clients
Turning on this feature may execute script code
without you explicitly opening the message
To turn off the preview feature in Microsoft 
Outlook:
 Go to View menu and select  Reading Pane
 Click the Off option
To turn off the preview feature in Mozilla 
Thunderbird:
 Go to View menu and select Layout
 Uncheck the option Message Pane
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27
Email Filtering: Avoiding Unwanted Emails
Email filtering is the process of organizing emails according to a specified criteria
Email filters are generally used to identify and categorize spam mails
To avoid unwanted emails in Outlook 2010, go to the Delete group on the Home tab, 
click Junk and Junk E‐mail Options, On the Blocked Sender  tab, click Add
Enter an email address or domain name, click OK
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28
Module Flow
Introduction to
Email Security
Email
Security Threats
Email
Security Procedures
How to Obtain
Digital Certificates?
Email
Security Tools
Copyright © by EC-Council
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29
Digitally SignYour Emails
Thwate (http://www.thawte.com)
Example of Certification Authorities:
VeriSign (http://www.verisign.com) Comodo (http://www.comodo.com)
Entrust (http://www.entrust.com)
 Digital signatures are used to authenticate the sender of a message or the signer 
of a document
 They can also be used to ensure that the original content of the message is not 
changed
 Users require an email certificate to digitally sign emails
 You can obtain digital signatures from certification authorities
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30
How to Obtain Digital Certificates?
Go to the Certificate Authorities 
website 
Purchase and download a digital 
certificate
Some certificate authorities offer a free 
personal email security certificate such 
as Comodo
Provide personal details to download 
the certificate
Login to the email account that you 
have provided while downloading the 
certificate
Check your inbox for an installation 
link 
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31
Installing a Digital Certificate
Click on the installation link to install the 
digital certificate
In Internet Explorer go to Tools  Internet 
Options  Content tab 
In the content tab, click Certificates button
Select the certificate and click the Export 
button
Click on Next
Check the Yes, export the private key option
Click on Next
Protect the private key by giving a password
and confirming it
Specify the file you want to export and save it 
to a particular location
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32
SigningYour Emails
Go to the Microsoft Outlook   File  Options
Click on Trust Center  Trust Center Settings  
 Email Security
Encrypt the mail by selecting the appropriate 
check boxes under  the Encrypted e‐mail section
Click the Import/Export button
Browse to find the file to open and give the 
password and digital ID name
Click the OK button
Click New Mail to write a message
After clicking on the Send button, it will prompt 
to encrypt the message
Click the Send Unencrypted button (if the 
recipients do not have private key)
Click on the Continue button if the recipient 
have private key
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33
SigningYour Emails
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34
Choose the Automatic Download option from the Trust Center and select the options 
as shown in the figure
Microsoft Outlook Download Settings
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35
Module Flow
Introduction to
Email Security
Email
Security Threats
Email
Security Procedures
How to Obtain
Digital Certificates?
Email
Security Tools
Copyright © by EC-Council
All Rights Reserved. Reproduction is Strictly Prohibited.
36
Online Email Encryption Service: Lockbin
Lockbin is a free service for sending private email messages
It is used for sending confidential information such as credit card details and business information
https://www.lockbin.com
Copyright © by EC-Council
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37
Email Security Tools
Comodo AntiSpam
http://www.comodoantispam.com
Netcraft Toolbar 
http://toolbar.netcraft.com
PhishTank SiteChecker
https://addons.mozilla.org
Mirramail Secure Email 
http://www.mirrasoft.com
Spamihilator
http://www.spamihilator.com
Encryptomatic MessageLock
http://www.encryptomatic.com
McAfee SpamKiller
http://us.mcafee.com
Comodo Email Certificate
http://www.comodo.com
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38
Module Summary
 Email (electronic mail) is a method of exchanging digital messages from a sender to 
one or more recipients
 Attachments can contain malicious programs; opening such attachments can infect 
the computer
 Spamming is the process of populating the user’s inbox with unsolicited or junk emails
 Hoaxes are false alarms claiming reports about a nonexistent virus
 Do not forget to delete browser cache, passwords, and history
 Consider setting mobile phones to download only headers of emails, not the full email 
 Digital signatures are used to authenticate the sender of a message or the signer of a 
document
 Email security tools protect passwords and automatically log off email accounts
Copyright © by EC-Council
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39
Email Communication Checklist
DON’T CLOSE the browser  without properly logging out
DON’T FORGET to delete browser cache, passwords, and history
DON’T SEND personal and financial information via email
DON’T USE just one email account for all purposes
DON’T TRUST the emails from your friends to be secure
DON’T DELETE spam instead of blacklisting it
DON’T FAIL to scan all email attachments and to enable the email 
spam filter
DON’T USE simple and easy‐to‐guess passwords
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40
Email Security Checklist
Enable https for secure communications/transactions
Be diligent while opening email attachments
Do not click on links provided in email messages 
Create strong passwords for logging into mail accounts
Follow email etiquette when forwarding messages
Do not forward or reply to spam and suspicious emails; delete them
Avoid accessing email via unsecured public wireless connection 
Avoid accessing the email accounts on shared computers and sending 
large attachments in emails
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41
Never save your password on the web browser
Sort messages by priority, subject, date, sender, and other options 
(Helps in searching email)
Avoid sending confidential, sensitive, personal, and classified 
information in emails
Use Bcc: option when sending mail to bulk recipients
Clean your Inbox regularly 
Create folders and move email accordingly (Family, Friends, Work, etc.)
Digitally sign your outgoing mails
Send attachments in PDF form rather than Word or Excel formats
Email Security Checklist
Copyright © by EC-Council
All Rights Reserved. Reproduction is Strictly Prohibited.
42
Configure to check only attachment notifications, but not 
attachments
Do not open/send large attachments from mobile
Do not follow links sent in email or text messages
Consider setting mobile phones to download only headers of emails, 
not the full email 
Install mobile antivirus and keep it up to date
Turn off Show Pictures in your Mobile Browser
To reduce the size of email, send them in plain text
Zip and send any important files
Security Checklist for Checking Emails on Mobile

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Cscu module 09 securing email communications