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Ethical Hacking 
CHAPTER 8 – WINDOWS VULNERABILITIES 
ERIC VANDERBURG
Objectives 
 Describe the tools available to assess Microsoft system 
vulnerabilities 
 Describe the vulnerabilities of Microsoft operating systems 
 Describe the vulnerabilities of services running on Microsoft 
operating systems 
 Explain techniques to harden Microsoft systems against 
common vulnerabilities 
 Describe best practices for securing Microsoft systems
Tools to Identify Vulnerabilities 
on Microsoft Systems 
 Many tools are available for this task 
 Using more than one tool is advisable 
 Using several tools help you pinpoint problems more 
accurately
Built-in Microsoft Tools 
 Microsoft Baseline Security Analyzer (MBSA) 
 Winfingerprint 
 HFNetChk
Microsoft Baseline Security 
Analyzer (MBSA) 
 Effective tool that checks for 
 Patches 
 Security updates 
 Configuration errors 
 Blank or weak passwords 
 Others 
 MBSA supports remote scanning 
 Associated product must be installed on scanned computer
Using MBSA 
 System must meet minimum requirements before installing 
MBSA on a computer 
 After installing, MBSA can 
 Scan itself 
 Scan other computers remotely 
 Be scanned remotely
HFNetChk 
 HFNetChk is part of MBSA 
 Available separately from Shavlik Technologies 
 Versions 
 Advanced command line 
 GUI 
 Scanning types 
 MBSA-style scan 
 HFNetChk-style scan 
 You must be an administrator on the scanned machine to run 
the scan
Winfingerprint 
 Administrative tool 
 It can be used to scan network resources 
 Exploits Windows null sessions 
 Detects 
 NetBIOS shares 
 Disk information and services 
 Null sessions
Winfingerprint (continued) 
 Its capabilities also include 
 ICMP and DNS resolution 
 OS detection 
 Service packs and hotfixes 
 Running modes 
 Passive 
 Interactive 
 Can be run on a single machine or the entire network 
 You can also specify IP addresses or ranges
Microsoft OS Vulnerabilities 
 Microsoft integrates many of its products into a single packet 
 Good software engineering practice 
 Creates a single point of failure 
 Security testers should search for vulnerabilities on 
 The OS they are testing 
 Any application running on the server 
 Good information sources 
 Common Vulnerabilities and Exposures (CVE) site 
 Vendor Web site
Remote Procedure Call (RPC) 
 RPC is an interprocess communication mechanism 
 Allows a program running on one host to run code on a remote 
host 
 Examples of worms that exploited RPC 
 MSBlast (LovSAN, Blaster) 
 Nachi 
 Use MBSA to detect if a computer is vulnerable to an RPC-related 
issue
NetBIOS 
 Software loaded into memory 
 Enables a computer program to interact with a network resource 
or other device 
 NetBIOS is not a protocol 
 NetBIOS is an interface to a network protocol 
 NetBEUI 
 Fast, efficient network protocol 
 Allows NetBIOS packets to be transmitted over TCP/IP 
 NBT is NetBIOS over TCP
NetBIOS (continued) 
 Newer Microsoft OSs do not need NetBIOS to share resources 
 NetBIOS is used for backward compatibility
Server Message Block (SMB) 
 Used by Windows 95, 98 and NT to share files 
 Usually runs on top of NetBIOS, NetBEUI or TCP/IP 
 Hacking tools 
 L0phtcrack’s SMB Packet Capture utility 
 SMBRelay
Common Internet File System (CIFS) 
 CIFS replaced SMB for Windows 2000, XP, and Windows 2003 
Server 
 SMB is still used for backward compatibility 
 Remote file system protocol 
 Enables computers to share network resources over the Internet 
 Relies on other protocols to handle service announcements
Common Internet File System (CIFS) 
(continued) 
 Enhancements over SMB 
 Resource locking 
 Caching and read-ahead/write-behind 
 Support for fault tolerance 
 Capability to run more efficiently over dial-up 
 Support for anonymous and authenticated access 
 Server security methods 
 Share-level security 
 User-level security
Understanding Samba 
 Open-source implementation of CIFS 
 Created in 1992 
 Samba allows sharing resources over multiple OSs 
 Samba accessing Microsoft shares can make a network susceptible 
to attack 
 Samba is used to “trick” Microsoft services into believing the *NIX 
resources are Microsoft resources
Understanding Samba (continued) 
 Enable sharing resources 
 Configure the Smb.conf file to include any shared files or printers 
 Run the Testparm to identify any syntax error in the Smb.conf file 
 User is prompted for a user name and password 
 Other files and commands 
 Smbpasswd file 
 Smbuser command
Closing SMB Ports 
 Best way to protect a network from SMB attacks 
 Routers should filter out ports 
 137 to 139 
 445
Passwords and Authentication 
 People legitimately using the system 
 Most vulnerable and difficult to secure 
 A comprehensive password policy is critical 
 A password policy should include 
 Change password regularly 
 Require passwords length of at least six characters 
 Require complex passwords 
 Never write a password down or store it online or on the local system 
 Do not reveal a password over the phone
Passwords and Authentication 
 Configure domain controllers 
 Enforce password age, length and complexity 
 Account lockout threshold 
 Account lockout duration
Vulnerabilities in Microsoft Services 
 Internet Information Services (IIS) 
 SQL Server
Web Services 
 IIS installs with critical security vulnerabilities 
 IIS Lockdown Wizard 
 IIS 6.0 installs with a “secure by default” posture 
 Previous versions left crucial security holes 
 Configure only services that are needed 
 Windows 2000 ships with IIS installed by default 
 Running MBSA can detect IIS running on your network
SQL Server 
 SQL vulnerabilities exploits areas 
 The SA account with a blank password 
 SQL Server Agent 
 Buffer overflow 
 Extended stored procedures 
 Default SQL port 1433 
 Vulnerabilities related to SQL Server 7.0 and SQL Server 2000
The SA Account 
 SQL Server 6.5 and 7 installations do not require setting a password 
for this account 
 SQL Server 2000 supports mixed-mode authentication 
 SA account is created with a blank password 
 SA account cannot be disabled
SQL Server Agent 
 Service mainly responsible for 
 Replication 
 Running scheduled jobs 
 Restarting the SQL service 
 Authorized but unprivileged user can create scheduled jobs to be 
run by the agent
Buffer Overflow 
 Database Consistency Checker in SQL Server 2000 
 Contains commands with buffer overflows 
 SQL Server 7 and 2000 have functions that generate text messages 
 They do not check that messages fit in the buffers supplied to hold them 
 Format string vulnerability in the C runtime functions
Extended Stored Procedures 
 Several of the extended stored procedures fail to perform input 
validation 
 They are susceptible to buffer overruns
Default SQL Port 1443 
 SQL Server is a Winsock application 
 Communicates over TCP/IP using port 1443 
 Spida worm 
 Scans for systems listening on TCP port 1443 
 Once connected, attempts to use the xp_cmdshell 
 Enables and sets a password for the Guest account 
 Changing default port is not an easy task
Best Practices for Hardening 
Microsoft Systems 
 Penetration tester 
 Finds vulnerabilities 
 Security tester 
 Finds vulnerabilities 
 Gives recommendations for correcting found vulnerabilities
Patching Systems 
 The number-one way to keep your system secure 
 Attacks take advantage of known vulnerabilities 
 Options for small networks 
 Accessing Windows Update manually 
 Automatic Updates 
 Options for patch management for large networks 
 Systems Management Server (SMS) 
 Software Update Service (SUS)
Antivirus Solutions 
 An antivirus solution is essential 
 For small networks 
 Desktop antivirus tool with automatic updates 
 For large networks 
 Corporate-level solution 
 An antivirus tool is almost useless if it is not updated regularly
Enable Logging and Review Logs 
Regularly 
 Important step for monitoring critical areas 
 Performance 
 Traffic patterns 
 Possible security breaches 
 Logging can have negative impact on performance 
 Review logs regularly for signs of intrusion or other problems 
 Use a log-monitoring tool
Disable Unused or Unneeded 
Services 
 Disable unneeded services 
 Delete unnecessary applications or scripts 
 Unused applications or services are an invitation for attacks 
 Requires careful planning 
 Close unused port but maintain functionality
Other Security Best Practices 
 Other practices include 
 Use TCP/IP filtering 
 Delete unused scripts and sample applications 
 Delete default hidden shares 
 Be careful of default permissions 
 Use appropriate packet-filtering techniques 
 Use available tools to assess system security 
 Disable the Guest account 
 Rename the default Administrator account 
 Make sure there are no accounts with blank passwords
Summary 
 Tools to discover vulnerabilities in Microsoft systems 
 Microsoft Baseline Security Analyzer (MBSA) 
 Winfingerprint 
 HFNetChk 
 MBSA 
 Effective tool that checks for patches, security updates, 
configuration errors, blank or weak passwords 
 Scan types 
 MBSA-style scan 
 HFNetChk-style scan
Summary (continued) 
 Winfingerprint 
 Free administrative tool 
 Used to scan network resources 
 It can detect NetBIOS shares, disk information, services, and null 
sessions 
 Microsoft’s integration of several products into one package 
creates a single point of failure 
 NetBIOS is used on newer Microsoft OSs for backward 
compatibility 
 Windows 95, 98, and NT use SMB to share files
Summary (continued) 
 CIFS replaced SMB for Windows 2000, XP, and Windows 2003 
Server 
 Samba is an open-source implementation of CIFS 
 Create a comprehensive password policy 
 Vulnerable Microsoft services 
 Web services (IIS) 
 SQL Server 
 Recommendations for securing Microsoft systems 
 Keep systems and antivirus updated 
 Disable unused ports and services

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Ethical hacking chapter 8 - Windows Vulnerabilities - Eric Vanderburg

  • 1. Ethical Hacking CHAPTER 8 – WINDOWS VULNERABILITIES ERIC VANDERBURG
  • 2. Objectives  Describe the tools available to assess Microsoft system vulnerabilities  Describe the vulnerabilities of Microsoft operating systems  Describe the vulnerabilities of services running on Microsoft operating systems  Explain techniques to harden Microsoft systems against common vulnerabilities  Describe best practices for securing Microsoft systems
  • 3. Tools to Identify Vulnerabilities on Microsoft Systems  Many tools are available for this task  Using more than one tool is advisable  Using several tools help you pinpoint problems more accurately
  • 4. Built-in Microsoft Tools  Microsoft Baseline Security Analyzer (MBSA)  Winfingerprint  HFNetChk
  • 5. Microsoft Baseline Security Analyzer (MBSA)  Effective tool that checks for  Patches  Security updates  Configuration errors  Blank or weak passwords  Others  MBSA supports remote scanning  Associated product must be installed on scanned computer
  • 6. Using MBSA  System must meet minimum requirements before installing MBSA on a computer  After installing, MBSA can  Scan itself  Scan other computers remotely  Be scanned remotely
  • 7. HFNetChk  HFNetChk is part of MBSA  Available separately from Shavlik Technologies  Versions  Advanced command line  GUI  Scanning types  MBSA-style scan  HFNetChk-style scan  You must be an administrator on the scanned machine to run the scan
  • 8. Winfingerprint  Administrative tool  It can be used to scan network resources  Exploits Windows null sessions  Detects  NetBIOS shares  Disk information and services  Null sessions
  • 9. Winfingerprint (continued)  Its capabilities also include  ICMP and DNS resolution  OS detection  Service packs and hotfixes  Running modes  Passive  Interactive  Can be run on a single machine or the entire network  You can also specify IP addresses or ranges
  • 10. Microsoft OS Vulnerabilities  Microsoft integrates many of its products into a single packet  Good software engineering practice  Creates a single point of failure  Security testers should search for vulnerabilities on  The OS they are testing  Any application running on the server  Good information sources  Common Vulnerabilities and Exposures (CVE) site  Vendor Web site
  • 11. Remote Procedure Call (RPC)  RPC is an interprocess communication mechanism  Allows a program running on one host to run code on a remote host  Examples of worms that exploited RPC  MSBlast (LovSAN, Blaster)  Nachi  Use MBSA to detect if a computer is vulnerable to an RPC-related issue
  • 12. NetBIOS  Software loaded into memory  Enables a computer program to interact with a network resource or other device  NetBIOS is not a protocol  NetBIOS is an interface to a network protocol  NetBEUI  Fast, efficient network protocol  Allows NetBIOS packets to be transmitted over TCP/IP  NBT is NetBIOS over TCP
  • 13. NetBIOS (continued)  Newer Microsoft OSs do not need NetBIOS to share resources  NetBIOS is used for backward compatibility
  • 14. Server Message Block (SMB)  Used by Windows 95, 98 and NT to share files  Usually runs on top of NetBIOS, NetBEUI or TCP/IP  Hacking tools  L0phtcrack’s SMB Packet Capture utility  SMBRelay
  • 15. Common Internet File System (CIFS)  CIFS replaced SMB for Windows 2000, XP, and Windows 2003 Server  SMB is still used for backward compatibility  Remote file system protocol  Enables computers to share network resources over the Internet  Relies on other protocols to handle service announcements
  • 16. Common Internet File System (CIFS) (continued)  Enhancements over SMB  Resource locking  Caching and read-ahead/write-behind  Support for fault tolerance  Capability to run more efficiently over dial-up  Support for anonymous and authenticated access  Server security methods  Share-level security  User-level security
  • 17. Understanding Samba  Open-source implementation of CIFS  Created in 1992  Samba allows sharing resources over multiple OSs  Samba accessing Microsoft shares can make a network susceptible to attack  Samba is used to “trick” Microsoft services into believing the *NIX resources are Microsoft resources
  • 18. Understanding Samba (continued)  Enable sharing resources  Configure the Smb.conf file to include any shared files or printers  Run the Testparm to identify any syntax error in the Smb.conf file  User is prompted for a user name and password  Other files and commands  Smbpasswd file  Smbuser command
  • 19. Closing SMB Ports  Best way to protect a network from SMB attacks  Routers should filter out ports  137 to 139  445
  • 20. Passwords and Authentication  People legitimately using the system  Most vulnerable and difficult to secure  A comprehensive password policy is critical  A password policy should include  Change password regularly  Require passwords length of at least six characters  Require complex passwords  Never write a password down or store it online or on the local system  Do not reveal a password over the phone
  • 21. Passwords and Authentication  Configure domain controllers  Enforce password age, length and complexity  Account lockout threshold  Account lockout duration
  • 22. Vulnerabilities in Microsoft Services  Internet Information Services (IIS)  SQL Server
  • 23. Web Services  IIS installs with critical security vulnerabilities  IIS Lockdown Wizard  IIS 6.0 installs with a “secure by default” posture  Previous versions left crucial security holes  Configure only services that are needed  Windows 2000 ships with IIS installed by default  Running MBSA can detect IIS running on your network
  • 24. SQL Server  SQL vulnerabilities exploits areas  The SA account with a blank password  SQL Server Agent  Buffer overflow  Extended stored procedures  Default SQL port 1433  Vulnerabilities related to SQL Server 7.0 and SQL Server 2000
  • 25. The SA Account  SQL Server 6.5 and 7 installations do not require setting a password for this account  SQL Server 2000 supports mixed-mode authentication  SA account is created with a blank password  SA account cannot be disabled
  • 26. SQL Server Agent  Service mainly responsible for  Replication  Running scheduled jobs  Restarting the SQL service  Authorized but unprivileged user can create scheduled jobs to be run by the agent
  • 27. Buffer Overflow  Database Consistency Checker in SQL Server 2000  Contains commands with buffer overflows  SQL Server 7 and 2000 have functions that generate text messages  They do not check that messages fit in the buffers supplied to hold them  Format string vulnerability in the C runtime functions
  • 28. Extended Stored Procedures  Several of the extended stored procedures fail to perform input validation  They are susceptible to buffer overruns
  • 29. Default SQL Port 1443  SQL Server is a Winsock application  Communicates over TCP/IP using port 1443  Spida worm  Scans for systems listening on TCP port 1443  Once connected, attempts to use the xp_cmdshell  Enables and sets a password for the Guest account  Changing default port is not an easy task
  • 30. Best Practices for Hardening Microsoft Systems  Penetration tester  Finds vulnerabilities  Security tester  Finds vulnerabilities  Gives recommendations for correcting found vulnerabilities
  • 31. Patching Systems  The number-one way to keep your system secure  Attacks take advantage of known vulnerabilities  Options for small networks  Accessing Windows Update manually  Automatic Updates  Options for patch management for large networks  Systems Management Server (SMS)  Software Update Service (SUS)
  • 32. Antivirus Solutions  An antivirus solution is essential  For small networks  Desktop antivirus tool with automatic updates  For large networks  Corporate-level solution  An antivirus tool is almost useless if it is not updated regularly
  • 33. Enable Logging and Review Logs Regularly  Important step for monitoring critical areas  Performance  Traffic patterns  Possible security breaches  Logging can have negative impact on performance  Review logs regularly for signs of intrusion or other problems  Use a log-monitoring tool
  • 34. Disable Unused or Unneeded Services  Disable unneeded services  Delete unnecessary applications or scripts  Unused applications or services are an invitation for attacks  Requires careful planning  Close unused port but maintain functionality
  • 35. Other Security Best Practices  Other practices include  Use TCP/IP filtering  Delete unused scripts and sample applications  Delete default hidden shares  Be careful of default permissions  Use appropriate packet-filtering techniques  Use available tools to assess system security  Disable the Guest account  Rename the default Administrator account  Make sure there are no accounts with blank passwords
  • 36. Summary  Tools to discover vulnerabilities in Microsoft systems  Microsoft Baseline Security Analyzer (MBSA)  Winfingerprint  HFNetChk  MBSA  Effective tool that checks for patches, security updates, configuration errors, blank or weak passwords  Scan types  MBSA-style scan  HFNetChk-style scan
  • 37. Summary (continued)  Winfingerprint  Free administrative tool  Used to scan network resources  It can detect NetBIOS shares, disk information, services, and null sessions  Microsoft’s integration of several products into one package creates a single point of failure  NetBIOS is used on newer Microsoft OSs for backward compatibility  Windows 95, 98, and NT use SMB to share files
  • 38. Summary (continued)  CIFS replaced SMB for Windows 2000, XP, and Windows 2003 Server  Samba is an open-source implementation of CIFS  Create a comprehensive password policy  Vulnerable Microsoft services  Web services (IIS)  SQL Server  Recommendations for securing Microsoft systems  Keep systems and antivirus updated  Disable unused ports and services