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Seven Deadliest Microsoft Attacks - 1st Edition - ISBN: 9781597495516, 9781597495523

Seven Deadliest Microsoft Attacks

1st Edition

Authors: Rob Kraus Brian Barber Mike Borkin Naomi Alpern
Paperback ISBN: 9781597495516
eBook ISBN: 9781597495523
Imprint: Syngress
Published Date: 17th March 2010
Page Count: 192
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Seven Deadliest Microsoft Attacks explores some of the deadliest attacks made against Microsoft software and networks and how these attacks can impact the confidentiality, integrity, and availability of the most closely guarded company secrets. If you need to keep up with the latest hacks, attacks, and exploits effecting Microsoft products, this book is for you. It pinpoints the most dangerous hacks and exploits specific to Microsoft applications, laying out the anatomy of these attacks including how to make your system more secure. You will discover the best ways to defend against these vicious hacks with step-by-step instruction and learn techniques to make your computer and network impenetrable.

The book consists of seven chapters that cover the seven deadliest attacks against Microsoft software and networks: attacks against Windows passwords; escalation attacks; stored procedure attacks; mail service attacks; client-side ActiveX and macro attacks; Web service attacks; and multi-tier attacks. Each chapter provides an overview of a single Microsoft software product, how it is used, and some of the core functionality behind the software. Furthermore, each chapter explores the anatomy of attacks against the software, the dangers of an attack, and possible defenses to help prevent the attacks described in the scenarios.

This book will be a valuable resource for those responsible for oversight of network security for either small or large organizations. It will also benefit those interested in learning the details behind attacks against Microsoft infrastructure, products, and services; and how to defend against them. Network administrators and integrators will find value in learning how attacks can be executed, and transfer knowledge gained from this book into improving existing deployment and integration practices.

Key Features

  1. Windows Operating System-Password Attacks
  2. Active Directory-Escalation of Privilege
  3. SQL Server-Stored Procedure Attacks
  4. Exchange Server-Mail Service Attacks
  5. Office-Macros and ActiveX
  6. Internet Information Serives(IIS)-Web Serive Attacks
  7. SharePoint-Multi-tier Attacks


Information security professionals of all levels; Micosoft admins; recreational hackers

Table of Contents


About the Authors


Chapter 1 Windows Operating System – Password Attacks

Windows Passwords Overview

Security Accounts Manager

System Key (SYSKEY)

LAN Manager Hash

NT Hash

LSA Secrets

Password and Lockout Policies

How Windows Password Attacks Work

Dangers with Windows Password Attacks

Scenario 1: Obtaining Password Hashes

Scenario 2: Pass the Hash

Scenario 3: Timed Attacks to Circumvent Lockouts

Scenario 4: LSA Secrets

Future of Windows Password Attacks

Defenses against Windows Password Attacks

Defense-in-Depth Approach

Microsoft and Third-Party Software Patching

Logical Access Controls

Logging Security Events

Implementing Password and Lockout Policies

Disable LM Hash Storage for Domain and Local Systems

SYSKEY Considerations


Chapter 2 Active Directory – Escalation of Privilege

Escalation of Privileges Attack Anatomy

Dangers with Privilege Escalation Attacks

Scenario 1: Escalation through Batch Scripts

Scenario 2: Attacking Customer Confidence

Scenario 3: Horizontal Escalation

Future of Privilege Escalation Attacks

Defenses against Escalation of Privilege Attacks

First Defensive Layer: Stop the Enemy at the Gate

Second Defensive Layer: Privileges Must Be Earned

Third Defensive Layer: Set the Rules for the Playground

Fourth Defensive Layer: You’ll Need That Secret Decoder Ring



Chapter 3 SQL Server – Stored Procedure Attacks

How Stored Procedure Attacks Work

Initiating Access

Accessing Stored Procedures

Dangers Associated with a Stored Procedure Attack

Understanding Stored Procedure Vulnerabilities

Scenario 1: Adding a Local Administrator

Scenario 2: Keeping Sysadmin-Level Access

Scenario 3: Attacking with SQL Injection

The Future of Stored Procedure Attacks

Defenses against Stored Procedure Attacks

First Defensive Layer: Eliminating First-Layer Attacks

Second Defensive Layer: Reduce the First-Layer Attack Surface

Third Defensive Layer: Reducing Second-Layer Attacks

Fourth Defensive Layer: Logging, Monitoring, and Alerting

Identifying Vital Attack Events

Fifth Defensive Layer: Limiting the Impacts of Attacks



Chapter 4 Exchange Server – Mail Service Attacks

How Mail Service Attacks Work

Mail Flow Architecture

Attack Points

Dangers Associated with Mail Service Attacks

Scenario 1: Directory Harvest Attacks

Scenario 2: SMTP Auth Attacks

Scenario 3: Mail Relay Attacks

The Future of Mail Service Attacks

Defenses against Mail Service Attacks

Defense in the Perimeter Network

Defense on the Internal Network

Supporting Services


Chapter 5 Office – Macros and ActiveX

Macro and Client-Side Attack Anatomy

Macro Attacks

ActiveX Attacks

Dangers Associated with Macros and ActiveX

Scenario 1: Metasploit Reverse TCP Connection

Scenario 2: ActiveX Attack via Malicious Website

Future of Macro and ActiveX Attacks

Macro and ActiveX Defenses

Deploy Network Edge Strategies

Using Antivirus and Antimalware

Update Frequently

Using Office Security Settings

Working Smart



Chapter 6 Internet Information Services – Web Service Attacks

Microsoft IIS Overview

File Transfer Protocol Publishing Service

WebDAV Extension


How IIS Attacks Work

Dangers with IIS Attacks

Scenario 1: Dangerous HTTP Methods

Scenario 2: FTP Anonymous Access

Scenario 3: Directory Browsing

Future of IIS Attacks

Defenses Against IIS Attacks

Disable Unused Services

Default Configurations

Account Security

Patch Management


Segregate IIS

Penetration Testing


IIS Lockdown


Chapter 7 SharePoint – Multi-tier Attacks

How Multi-tier Attacks Work

Multi-tier Attack Anatomy

Dangers with Multi-tier Attacks

Scenario 1: Leveraging Operating System Vulnerabilities

Scenario 2: Indirect Attacks

How Multi-tier Attacks Will Be Used in the Future

Defenses against Multi-tier Attacks

First Defensive Layer: Failure to Plan = Plan to Fail

Second Defensive Layer: Leave No Hole Unpatched

Third Defensive Layer: Form the Protective Circle





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© Syngress 2010
17th March 2010
Paperback ISBN:
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About the Authors

Rob Kraus

Rob Kraus (CISSP, C|EH, MCSE) is a Senior Security Consultant for Solutionary, Inc. Rob is responsible for organizing customer requirements, on-site project management and client support while ensuring quality and timeliness of Solutionary's products and services.

Rob was previously a Remote Security Services Supervisor with Digital Defense, Inc. He performed offensive-based security assessments consisting of penetration testing, vulnerability assessment, social engineering, wireless and VoIP penetration testing, web application penetration tests and vulnerability research. As a supervisor, Rob was also responsible for leading and managing a team of penetration testers who performed assessment services for Digital Defense's customers.

Rob's background also includes contracting as a security analyst for AT&T during the early stages of the AT&T U-verse service as well as provisioning, optimizing, and testing OC-192 fiber-optic networks while employed with Nortel Networks.

Rob also speaks at information security conferences and universities in an effort to keep the information security community informed of current security trends and attack methodologies.

Affiliations and Expertise

CISSP, C|EH, MCSE; Senior Security Consultant for Solutionary, Inc.

Brian Barber

Brian Barber (Linux+, MCSE, MCSA, MCP+I, CNE, CNA-GW) works for the Canada Deposit Insurance Corporation (CDIC) as a project manager and architect for CDIC's IT service management program. He first started using Linux at home with Red Hat 5.1 and since then he has been a staunch advocate of open source software, belonging to the Ottawa Canada Linux User Group (OCLUG) since 2001 and the Ottawa Python Authors Group. His primary areas of interest are operating systems, infrastructure design, multiplatform integration, directory services, and enterprise messaging. In the past he has held the positions of Principal Consultant with Sierra Systems Group Inc., Senior Technical Coordinator at the LGS Group Inc. (now a part of IBM Global Services) and Senior Technical Analyst at MetLife Canada.

Affiliations and Expertise


Mike Borkin

Mike Borkin (MCSE, GSEC Gold) is an internationally recognized author and speaker in the area of IT security where he focuses mostly on data protection strategies, Microsoft security, and security architecture/engineering best practices. In addition to contributing articles related to security to magazines and speaking engagements for groups such as SANS and The Open Group in both the US and Europe, Mike is also the Co-Author of Vista Security for Dummies.

Affiliations and Expertise


Naomi Alpern

Naomi Alpern currently works for Microsoft as a consultant specializing in unified communications. She holds many Microsoft certifications, including an MCSE and MCT, as well as additional industry certifications such as Citrix Certified Enterprise Administrator, Security+, Network+, and A+. Since the start of her technical career she has worked in many facets of the technology world, including IT administration, technical training, and most recently, full-time consulting.

Affiliations and Expertise

Consultant, Unified Communications, Microsoft, USA, Citrix Certified Enterprise Administrator, Security+, Network+, A+, MCSE, MCT


"Seven Deadliest Microsoft Attacks brings to light easily exploitable yet commonly overlooked vulnerabilities of Microsoft systems. The real-world examples used help reinforce the magnitude of these attacks, all while depicting the simplicity of the attack itself. The authors end on a good note with steps to avoid becoming a victim and insight on industry trends."--Aaron Beauregard, IT Systems and Security Manager, Mueller Services, Inc.

"The text is peppered with warnings, notes, recommendations and so-called 'Epic Fail' text boxes that illustrate some of the typical mistakes made when working with that particular software...The bok and the chapters are short, but long enough to give a good overview of today's most common attacks targeting some of the most popular Microsoft products."--Zeljka Zorz, Help Net Security


Ratings and Reviews