ECSA/ LPT EC Council Module XXXIX EC - Council Email Security Penetration Testin g g Penetration Testing Roadmap Start Here Information Vulnerability External Gathering Analysis Penetration Testing Fi ll Router and Internal Fi rewa ll Penetration Testing Router and Switches Penetration Testing Internal Network Penetration Testing IDS Penetration Testing Wireless Network Penetration Testing Denial of Service Penetration Testing Password Cracking Stolen Laptop, PDAs and Cell Phones Social Engineering Application Cont’d EC-Council Copyright © by EC-Council All Rights Reserved. Reproduction is Strictly Prohibited Penetration Testing Penetration Testin g Penetration Testing Penetration Testin g Penetration Testing Roadmap (cont ’ d) (cont d) Cont’d Ph y sical Database VoIP y Security Penetration Testing Penetration testing Penetration Testing Virus and Trojan Detection War Dialing VPN Penetration Testing Log Management Penetration Testing File Integrity Checking Blue Tooth and Hand held Device Penetration Testing Penetration Testing Telecommunication And Broadband Email Security Penetration Testing Security Patches Data Leakage End Here EC-Council Copyright © by EC-Council All Rights Reserved. Reproduction is Strictly Prohibited Communication Penetration Testing Penetration Testing Patches Penetration Testing Penetration Testin g Introduction to Email Security Email accounts are the re p ositories where p eo p le store their ppp private information or even their business data. Due to the widespread use of the Internet techniques and tools, a hacker can access the user’s ID and email password. EC-Council Copyright © by EC-Council All Rights Reserved. Reproduction is Strictly Prohibited Pre-Requisite For Email Penetration Testing Penetration Testing E il dd hi h f E ma il a dd ress on w hi c h you want to per f orm penetration testing EC-Council Copyright © by EC-Council All Rights Reserved. Reproduction is Strictly Prohibited Steps for Email Penetration Testing Testing 1 • Try to access email ID and password 2 • Check whether anti-phishing software is enabled • Check whether anti - spamming tools are enabled 3 • Check whether anti - spamming tools are enabled 4 • Try to perform email bombing 5 • Perform CLSID extension vulnerability test 6 • Perform VBS attachment vulnerabilit y test 6 y 7 • Perform double file extension vulnerability test EC-Council Copyright © by EC-Council All Rights Reserved. Reproduction is Strictly Prohibited 8 • Perform long filename vulnerability test Steps for Email Penetration Testing (cont ’ d) Testing (cont d) 9 • Perform ActiveX vulnerability test 10 • Perform IFrame remote vulnerability test 11 • Perform MIME header vulnerability test • Perform malformed file extension vulnerabilit y test 12 y 13 • Perform access exploit vulnerability test 14 • Perform fragmented message vulnerability test Pf l bj h hki EC-Council Copyright © by EC-Council All Rights Reserved. Reproduction is Strictly Prohibited 15 • P er f orm l ong su bj ect attac h ment c h ec ki ng test Step 1: Try to Access Email ID and Password and Password Use social engineering Use social engineering techniques to get hint for user names and passwords. See the hint for forgotten See the hint for forgotten passwords. Use different password cracking tools, such as Hydra and John the Ripper to EC-Council Copyright © by EC-Council All Rights Reserved. Reproduction is Strictly Prohibited and John the Ripper to access the password. Step 2: Check Whether Anti- Phishing Software are Enabled Phishing Software are Enabled Send the mail containing a malicious link that redirects to Send the mail containing a malicious link that redirects to the malicious site. Ch k hth th il i bl k d b ti hi hi tl Ch ec k w h e th er th ema il i s bl oc k e d b yanyan ti -p hi s hi ng t oo l such as Netcraft. EC-Council Copyright © by EC-Council All Rights Reserved. Reproduction is Strictly Prohibited Step 3: Check Whether Anti- Spamming Tools are Enabled Spamming Tools are Enabled Use different bulk emailing tools, such as Fairlogic WorldCas and Handymailer to send the spam mail Check whether anti spamming tools are enabled or not WorldCas and Handymailer to send the spam mail . Check whether anti - spamming tools are enabled or not . Check if the spam mails are marked as spam or blocked. EC-Council Copyright © by EC-Council All Rights Reserved. Reproduction is Strictly Prohibited [...]... AEVITA Stop SPAM Email SpamExperts Desktop Spa SpamEater Pro ate o SpamWeasel Spytech SpamAgent AntispamSniper Spam Reader Spam Assassin Proxy (SA) Proxy MailWasher Free Spam Bully EC-Council Copyright © by EC-Council All Rights Reserved Reproduction is Strictly Prohibited AEVITA Stop SPAM Email AEVITA Stop SPAM Email helps to hide email addresses from spambots b t It will replace all the email addresses... attachment, e email is vulnerable to a long filename attack EC-Council Copyright © by EC-Council All Rights Reserved Reproduction is Strictly Prohibited Step 9: Perform ActiveX Vulnerability Test The Microsoft virtual machine (Microsoft VM) includes a security vulnerability that may allow script code in a web page or HTML based HTML-based email message to access ActiveX controls Send an HTML-based email message... Class ID (CLSID) file extension to the email ID Go to the mail and try to read the mail If you can run this attachment, the email is vulnerable to CLSID extension attack EC-Council Copyright © by EC-Council All Rights Reserved Reproduction is Strictly Prohibited Step 6: Perform VBS Attachment Vulnerability Test Send the attachment h with VBS file extension to the email ID EC-Council Go to the mail and... asking you l h d ki to open a the file, the email system is vulnerable to the attack Copyright © by EC-Council All Rights Reserved Reproduction is Strictly Prohibited Step 11: Perform MIME Header Vulnerability Test HTML emails are simply web pages; IE can render them and open binary attachments in a way that is appropriate to their MIME types Send the HTML email containing an executable attachment with... as HTA, to the email ID Go to the mail and try to read the mail mail If you can run this attachment, the email is vulnerable to this attack EC-Council Copyright © by EC-Council All Rights Reserved Reproduction is Strictly Prohibited Step 13: Perform Access Exploit Vulnerability Test Se d t e e containing t e V Send the file co ta g the VBA (Visual Basic for Applications) code to the email ID Go to... the email ID Go to the mail and try to read the mail If you will get the single mail with the attachment containing the virus name, the email is vulnerable to this attack EC-Council Copyright © by EC-Council All Rights Reserved Reproduction is Strictly Prohibited Step 15: Perform Long Subject Attachment Checking Test Send the mail with long subject name and attach the file with the same name as email s... Subject Attachment Checking Test Send the mail with long subject name and attach the file with the same name as email s subject and give DAT extension email s DAT extension Access the mailbox and try to read the email If you can run this attachment, the email system is vulnerable to this y , y attack EC-Council Copyright © by EC-Council All Rights Reserved Reproduction is Strictly Prohibited Anti-Phishing... Reserved Reproduction is Strictly Prohibited GFI MailEssentials GFI MailEssentials’ anti-phishing module detects and blocks threats posed by phishing emails It updates the database of blacklisted mails which ensures that all latest phishing mails are captured It also checks for typical phishing keywords in every email sent to the organization organization EC-Council Copyright © by EC-Council All Rights Reserved... you can run this attachment, the email is vulnerable to VBS extension attack tt k Copyright © by EC-Council All Rights Reserved Reproduction is Strictly Prohibited Step 7: Perform Double File Extension Vulnerability Test Send the double extension file to the email ID Go to the mail a d t y to read t e mail t e a and try ead the a If you can run this attachment, the email is vulnerable to double file... the email addresses on the page with specifically encoded email addresses addresses It introduces codes that spambots block, which a normal mailing program ignores It even stops spammers from getting a large list of email addresses EC-Council Copyright © by EC-Council All Rights Reserved Reproduction is Strictly Prohibited AEVITA Stop SPAM Email: Screenshot EC-Council Copyright © by EC-Council All . and Internal Fi rewa ll Penetration Testing Router and Switches Penetration Testing Internal Network Penetration Testing IDS Penetration Testing Wireless Network Penetration Testing Denial of Service Penetration. Penetration Testing Penetration Testin g Penetration Testing Penetration Testin g Penetration Testing Roadmap (cont ’ d) (cont d) Cont’d Ph y sical Database VoIP y Security Penetration Testing Penetration. Strictly Prohibited Communication Penetration Testing Penetration Testing Patches Penetration Testing Penetration Testin g Introduction to Email Security Email accounts are the re p ositories