PRACTICAL APPROACH FOR SECURING WINDOWS ENVIRONMENT: ATTACK VECTORS AND COUNTERMEASURES

International Journal of Network Security & Its Applications (IJNSA) Vol.9, No.6, November 2017
DOI: 10.5121/ijnsa.2017.9602 13
PRACTICAL APPROACH FOR SECURING WINDOWS
ENVIRONMENT: ATTACK VECTORS AND
COUNTERMEASURES
Abdurrahman Pektaş1
and Ertuğrul Başaranoğlu2
1
Department of Computer Engineering, Galatasaray University, Istanbul, Turkey 2
Ziraat
Technology, Istanbul, Turkey
ABSTRACT
Today, with the advancement of information technology, companies need to use many technologies,
platforms, systems and applications to effectively maintain their daily operations. This technology
dependence has created a serious complexity in the business network which increases the attack surface
and attracts cyber criminal’s attention. As a result, the number of cyber-attacks targeting corporate
environment is dramatically increased. To identify security holes in a network, penetration tests are
performed by internal sources (employees) and external sources (outsource companies or third parties).
Microsoft domain penetration testing,is one of the most important scopes of penetration testing, which
aims to expose the weaknesses in Microsoft domain environment. If the domain environment is not
structured securely, it can be abused by attackers and causes serious damage to the organization. In this
study, we present a penetration methodology for Windows domain environment called MSDEPTM
providing key metrics for Microsoft domain penetration testing. More specifically, the fundamental steps of
the attack vectors from the hacker point of view, root causes of these attacks, and countermeasures against
the attacks are discussed.
KEYWORDS
Penetration testing, Microsoft domain environment, securing Windows, information security, vulnerability
assessment
1. INTRODUCTION
Nowadays, information security has become more and more important issue both for individuals
and corporate entities or associations. Corporates tend to protect their computing infrastructure
and critical assets from attackers by applying security countermeasures. As it is well-known fact
that one of the most important environments in a corporate network is Microsoft domain
environment. For this reason, the cyber criminals highly target Microsoft domain. To ensure
security in a corporate network, system administrators and security teams defend domain
environment either in offensive and defensive ways.
Penetration testing, one of the most effective way to secure a network, can be defined as a
technique for exploring the existing security holes and vulnerabilities in a computing system or a
network to protect information assets before real attackers exploit them. The primary aim of the
penetration testing is to discover the ways to hack a system from hacker’s perspective. Microsoft
penetration testing is one of the most important measurement to secure the assets and systems that
are joined to the domain and it is also important to secure related (or connected) systems with
Microsoft active directory.

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Generally, the penetration testing can be divided into two categories black-box and white box. In
black box penetration testing, the pentesters aim to exploit the computer system remotely without
any prior knowledge. On the other hand, the white box penetration testing, the internal attacker
who already knows internal networks and possible weaknesses in these networks assess the
security level [1-3].
Although many pentesting methodologies exist, there is not enough research on Windows
penetration testing. In this paper, we present a penetration testing methodology focused on the
analysis of the Microsoft domain environment. We discuss different techniques, as well as
possible countermeasures available to mitigate attack vectors and vulnerabilities. Specifically,
every step of the proposed methodology is described in detail and comprehensively, such as the
tools, attack vectors, root causes, as well as countermeasures.
The reminder of the paper is organized as follows: the following section presents the related
works. Section 3 describes the proposed penetration test methodology for Microsoft Windows
domain environment. Section 4 introduces the countermeasures against the presented attack
scenarios. Finally, conclusions are presented in Section 5.
2. RELATED WORK
2.1. PENETRATION TESTING
There are different methodologies to conduct penetration testing. In general, the penetration
testing can be split into four phases: reconnaissance, scanning, exploitation and gaining persistent
access. These four steps can be extended into sub-phases such as post exploitation, password
cracking, vulnerability analysis, etc. Some of the current related works in penetration testing are
given as follows:
In [4], Setiawan et al. present the general steps about conducting penetration testing focussing on
finding and exploiting vulnerabilities in Windows OS. In the experiments, some steps of the
pentesting including scanning vulnerabilities, brute-force password guessing, gaining persistent
access to the computer via backdoors, privilege escalation, etc. are analyzed.
In [5], the authors analyzed the vulnerabilities and attacks targeting of the wireless
communication by performing the penetration test in a laboratory environment. The authors
developed a wireless auditing tool which is capable of detecting denial of service attacks, rouge
access points and WEP/WPA/WPA2 pre-shared cracking.
In [6], penetration testing and auditing of the Linux OS is presented. Various types of attack
vectors are analyzed in detail. Moreover, the author discussed the network auditing process and
forensic investigation in order to be used their research as a reference for security practitioners to
prevent cyber-attacks. [7] proposed an heuristic-based attack graph generation approach
integrating different stages of security assessment process. The authors also recommend cost-
driven mitigations for vulnerabilities.
Mehtre et al. [8] present the current trends of pen testing and vulnerability assessment. Then, they
the introduce step by step guide for vulnerability assessment and penetration testing. The use case
of some open source tools which are frequently used for performing penetrations testing is given
with hints related to these tools. The interested readers can refer to [9-12] for additional works.

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2.2. PENETRATION TESTING METHODOLOGIES
There are variety of standards, guidelines and methodologies that are prepared by organizations
to carry out penetration testing in an orderly fashion. These can be listed as follows:
PTES (Penetration Testing Execution Standard): PTES [13] is prepared by a group of people
that work in different sectors. It presents a penetration testing methodology that consists of 7
sections: pre-engagement interactions, intelligence gathering, threat modelling, vulnerability
analysis, exploitation post-exploitation and reporting. Although PTS is well prepared, it has not
yet been finalized. This standard forms a framework for all scopes of pen testing and draws a
general framework for all categories of penetration testing (for example, web, wireless, Microsoft
domain, network equipment, etc.). However, MSDEPTM provides penetration testing steps
specifically to the Microsoft domain environment and does not include the first and last steps of
the PTES. These steps present additional techniques (such as using built-in command sets or
getting the dump file of the LSASS process) against situations where an attack method is
unsuccessful (such as could not obtaining a Meterpreter shell) or an attack is not feasible (such as
running Mimikatz tool [14] on critical servers). In addition, PTS does not presents the
countermeasures against each attack step and technique.
CEH (Certified Ethical Hacker): CEH [15] is prepared by Ec-Council. It presents a penetration
testing methodology that consists of 5 phases: reconnaissance, scanning-enumeration, gaining
access, maintaining access and clearing tracks. The penetration test phases provided by CEH
cover all attack steps like MSDEPTM and CEH. It also contains best practices for planning and
reporting steps. In addition, CEH lists the different tools used in the penetration tests and
countermeasures against each attack like MSDEPTM, but CEH does not examine each step with
different techniques and does not provide in-depth penetration testing of Windows domain.
OSSTMM (The Open Source Security Testing Methodology Manual): OSSTMM [16] is
prepared by ISECOM (The Institute for Security and Open Methodologies). It presents a
penetration testing methodology that consists of 6 sections: information security, process security,
Internet technology security, communications security, wireless security and physical security.
OSSTMM explores penetration testing in general and theoretical perspective and introduces a
control-based methodology.
OWASP TG (Open Web Application Security Project Testing Guide): OWASP TG [17] is
prepared by OWASP (Open Web Application Security Project). It presents a penetration testing
methodology that consists of 10 sections: configuration and deployment management, identity
management, authentication, authorization, session management, data validation, testing for error
handling, testing for weak cryptography, business logic testing and client side testing. The
OWASP guide merely describes web application penetration testing in a very detailed fashion
including attack steps and techniques with various tools, examples and possible countermeasures.
ISSAF (Information Systems Security Assessment Framework): ISSAF [18] is prepared by
Open Information Systems Security Group (OISSG). ISSAF – is a three-phase framework that
aims to provide security assessment for real-world scenarios. The Second phase of ISSAF
presents a penetration testing methodology consisting of 9 steps: information gathering, network
mapping, vulnerability identification, penetration, gaining access and privilege escalation,
enumerating further, compromise remote users/sites, maintaining access and cover tracks. Like
other methodologies, ISSAF does not cover all attack vectors targeting Windows OS.

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3. MICROSOFT DOMAIN ENVIRONMENT PENETRATION TEST
METHODOLOGY
In this section, we present a penetration methodology for Windows domain environment. The
proposed methodology includes a set of attack vectors that consists of a specific set of tools and
techniques. MSDEPTM leads us to exploit the entire Windows domain.
The ultimate goal of Windows penetration testing is to gain Windows domain admin privileges
and thereby get control on the entire domain components [19-21]. For example, a domain admin
can login to any computer and access all files, processes, registry hives, etc. By default, the most
important privileges on a local Windows machine are administrators group and SYSTEM user; in
a Microsoft domain environment (i.e. active directory server) are domain admins or enterprise
admins groups. Generally, during penetration tests, a pentester requests a standard user account
and a computer which is provided to a new starting employee by company.
MSDEPTM consists of 10 steps as shown in Figure 1. As show in Figure 1, the proposed
methodology has 2 starting points. First one is gaining local administrator (or SYSTEM) user
privileges on the given computer by breaking physical security. The second start point is the
network scanning step. During penetration test, critical information is collected from
compromised systems (or network) and pentester tries to compromise new systems to achieve
more critical information and privileged accounts. If necessary, privilege escalation attacks,
pivoting, bypassing endpoint security applications can be performed to achieve this goal.
After having domain admin (or enterprise admin) privileges, some outputs of the Microsoft
domain environment penetration tests are shared with other pentest concepts such as the database,
web application etc., or vice versa. The details of each step along with different techniques of
MSDEPTM is elaborated in the following subsections.
Figure 1. The overview of the proposed Microsoft domain penetration testing methodology

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3.1. BYPASSING PHYSICAL SECURITY
Accessing disk system and getting SYSTEM privileges on a standard domain computer is one of
the first steps in Microsoft domain environment penetration testing. To bypass physical security a
Linux live image that has NTFS module can be used [22, 23]. This step can be analyzed under in
two different headings: accessing disk system and accessing session.
Accessing Disk System: By accessing disk system of a PC, user and system critical files can be
collected. For example, C:∖Users directories or subdirectories such as desktop or downloads,
backup directories, separated disk drives are important files and all of these files can be exported
by accessing file disk. Besides these objects, SAM and SYSTEM files are the most important two
files which hold local user names and password hashes. By exploiting these two files, pentesters
can acquire local users and password hashes which are used in the following attack strategies, like
pass the hash attack, and password cracking. Two main techniques can be used for this step:
• Technique - 1: samdump [24] and bkhive [25] command line tools can be used.
• Technique - 2: Ophcrack tool [26] can be used.
Accessing Session: By accessing disk system, pentesters aim to get SYSTEM privileges on the
computer. After getting SYSTEM privileges, it is possible to log on this computer by a new
administrator user. Three main techniques can be used for this step:
• Technique - 1: Applications that can be accessed on Windows logon screen such as
sethc.exe, utilman.exe, magnify.exe, osk.exe, narrator.exe can be replaced with Windows
command line tool (cmd.exe).
• Technique - 2: By using Launch Start-up Repair trick, it is possible to access disk system
without using a live image. After accessing disk system, the previous technique
(Technique - 1) can be performed.
• Technique - 3: It is possible to reset an administrator user password or create a new
administrator user by using chntpw [27] tool.
3.2. COMPROMISING SYSTEM
By exploiting operating system, server-side application or configuration vulnerabilities, it is
possible to access user or system privilege on a remote computer. It is also possible to
compromise a computer by using client-side attacks, for example, web-based attacks. In this
research, we only analyzed server-side vulnerabilities in three headings.
Exploiting Operating System Vulnerabilities: Remotely accessible services on Windows OS
such as RemoteRPC, SAMBA shares, etc. can include some critical vulnerabilities. These
vulnerabilities can be used by pentester to compromise a machine. MS03-026, MS04-007, and
MS08-067 are the most common vulnerabilities in Windows services.
Exploiting Application Vulnerabilities: Third party server applications installed on Windows
OS might have critical vulnerabilities. An attacker can compromise systems by exploiting these
vulnerabilities. A chat and freesshed applications are examples of such kind of applications.
Exploiting Configuration Vulnerabilities: The most common vulnerability in corporate domain
environment is that the IT administrators generally use the same user account with the same
credentials (i.e. same username and password). The main reason behind this vulnerability is that
the IT stuff employs the same disk image for all computers. By having plain text password (or

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even password hash) obtained from a compromised computer, it is possible to compromise other
computers by using the same credentials. Two main techniques can be used for this step:
• Technique - 1: Sysinternals’ Psexec tool [28], provided by Windows, can be used to
compromise remote computer by using local administrator’s plain text password.
However, the main limitation of psexec is that it does not support authentication with user
hashes.
• Technique - 2: Metasploit Framework’s (MSF) [29] psexec or psexec_psh modules can
be used to compromise remote computer by using local administrator password or hash.
3.3. PRIVILEGE ESCALATION
After getting access to a computer, privilege escalation step is generally needed to access more
sensitive information. Privilege escalation can be performed in various forms such as from
standard local user to local administrator, from local administrator to local SYSTEM, from the
SYSTEM user to a domain user, from domain user to Domain Administrator user etc. Four main
techniques can be used for this step:
• Technique - 1: Sysinternals Psexec tool can be used to escalate privileges from local
administrator account to SYSTEM account.
• Technique - 2: MSF bypassuac_injection module or custom scripts can be used to
escalate privileges from restricted environment to less restricted one.
• Technique - 3: Operating system vulnerabilities such as MS10-015, MS13-053, MS15-
051, and MS16-032 can be used to escalate privileges from standard user to SYSTEM
account.
• Technique - 4: Operating system vulnerabilities such as MS14-068 can be used to
escalate privileges from standard domain user to domain admin account.
It is also possible to escalate privileges by capturing tokens or passwords of logged on users.
These techniques will be introduced in the subsection 3.4.
3.4. COLLECTING CRITICAL INFORMATION FROM THE COMPROMISED SYSTEM
Collecting information from a compromised system is one of the most important steps in
penetration testing [30, 31]. User names, groups, domain information, password hashes of local
users, currently logged on user accounts and their tokens, plain text passwords that are stored on
the memory or disk can dramatically affect the success of penetration testing. This step can be
analyzed with five different subtitles.
Information about Local System and Domain: One of the first steps on a compromised system
is gathering information about the system. Local users (and passwords or hashes) and groups,
domain objects such as domain users and groups, group policies, network shares, network
information, installed applications, etc. are very useful and firstly collected by pentesters after
exploiting a Windows OS.
Password Hashes and Related Files: Local or domain user’s password hashes and related files -
such as SAM, SYSTEM and NTDS.dit - are very important for Microsoft domain environment.
The password hashes are used for pass-the-hash attacks. Windows OS allows users to authenticate
to remote Windows machine by using the hash of a user’s password. Besides that, these hashes
can also be cracked by brute force or dictionary attacks. John the Ripper [32], Ophcrack and Cain

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& Abel [33] tools can be used for cracking password hashes. Four main techniques can be used
for this step:
• Technique - 1: Local administrator user can get a copy of SAM and SYSTEM file from
registry hive by using a registry editing tool.
• Technique - 2: Local administrator users can get password hashes by using hacking tools
such as Cain & Abel and fgdump [34].
• Technique - 3: Password hashes can be exported from SAM and SYSTEM files by using
Linux Ophcrack tool, Linux samdump2 or bkhive tools, Windows Cain & Abel tool, etc.
• Technique - 4: Local or domain password hashes can be extracted by using Meterpreter
hashdump command, MSF hashdump or smart_hashdump modules.
• Technique - 5: NTDS.dit and SYSTEM files can be exported by using volume shadow
copy feature and domain password hashes can be extracted by esedbtools [35] and
ntdsxtract [36] tools.
Tokens on Memory: Tokens impersonate users. This feature makes tokens important. Two main
• Technique - 1: Meterpreter commands such as steal_token and migrate or incognito
extension can be used for token impersonation.
• Technique - 2: Custom Powershell scripts such as InvokeTokenManipulation [37] can be
used for token impersonation.
Clear Text Passwords on Memory: Clear text passwords of logged on users can be captured
from memory. Two main techniques can be used for this step:
• Technique - 1: WCE [38] and Mimikatz executable files can be used.
• Technique - 2: LSASS process dump file can be used.
Information on the Disk System: Passwords, backup files and recently used files can also be
useful during the test. Three main techniques can be used for this step:
• Technique - 1: Powershell commands or scripts can be used to collect critical information
from the file system.
• Technique - 2: Saved logon user credentials can be captured from applications.
• Technique - 3: Saved user credentials on group policies can be decrypted.
3.5. MAINTAINING THE PERSISTENCE
After compromising a computer system, the gaining persistent access is really beneficial while
conducting pentest. Three fundamental techniques can be used for this step:
• Technique - 1: Auto start mechanisms such as Autorun, registries, services, DLLs can be
used. Meterpreter persistence command is automatized for this step.
• Technique - 2: "Image File Execution Options" registry hive can be employed.

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• Technique - 3: The Golden ticket that can be created by using krbtgt user password hash
can be used to maintain the access to Microsoft domain environment.
3.6. PIVOTING TO UNREACHABLE NETWORKS
It is essential to further enumerate and reach to other networks and systems, which is called
pivoting. Through pivoting, pentester can gain access to unreachable network via the
compromised machine. Two main techniques can be used for this step:
• Technique - 1: Meterpreter route or portfwd commands, MSF autoroute post or socks4a
auxiliary modules, Linux proxy chains tool [39] can be used.
• Technique - 2: Remote desktop connection or standard command line over the
compromised system can be used.
3.7. NETWORK SCANNING
Identifying all computers and services offered in a network helps to compromise PCs. By default,
445/TCP and 139/TCP ports are opened on Windows systems. If remote desktop is enabled on the
computer, then 3389/TCP port is opened. To discover Windows machine these ports can be
scanned with the help of network scanning tools such as Nmap [40], Zenmap [41], Ncat [42],
Hoping [43], etc.
3.8. VULNERABILITY SCANNING
After discovering open services on Windows systems, identifying vulnerabilities is an important
step towards the hacking computer. Two main techniques can be used for this step:
• Technique - 1: Vulnerability scanners such as Nessus [44], Nexpose [45], Qualys [46] or
OpenVAS [47] can be used to identify vulnerabilities on the remote computers.
• Technique - 2: Scripts such as WindowsExploit-Suggester [48] or Windows Privesc
Check [49] can be used to identify vulnerabilities on the compromised system.
3.9 COLLECTING CRITICAL INFORMATION FROM NETWORK
Sometimes, domain users share sensitive information with their colleague via network shares
such as SMB, NFS, FTP without using any access restriction. Moreover, some of the network
services use clear text passwords in network transmission, which helps pentesters to collect them
by sniffing network traffic. Two main techniques can be used for this step:
• Technique - 1: Sniffer tools like tcpdump [50], Wireshark [51], Cain & Abel, Ettercap
[52] can be used to collect information on the network.
• Technique - 2: Metasploit modules, Nmap scripts, custom batches or scripts can be used
to discover network shares.
3.10. IDENTIFYING ACCESSIBLE SYSTEMS AND USERS
After collecting user credentials from all compromised systems or other fields of penetration
testing, pentester tries to spread on the domain environment as much as possible. Three main

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• Technique - 1: Hydra [53], Medusa [54], Ncrack tools [55] or Crowbar (formerly known
as Levye) script [56] can be used with plain text credentials to identify possibly
accessible Windows computers.
• Technique - 2: MSF smb_login can be used with password hashes or plain text password
to identify possibly accessible Windows systems.
• Technique - 3: MSF smb_enumusers_domain or psexec_loggedin_users modules can be
used to identify logged on users on possibly accessible Windows systems
4. MITIGATIONS AGAINST MICROSOFT DOMAIN ENVIRONMENT ATTACKS
There has been a significant increase in the cyber-attacks over the past decades. Consequently, the
states, companies and even individuals are obliged to secure and to defend their information
carefully. The following recommendations are vital for securing Windows domain and mitigating
against attacks targeting Microsoft domain environment that are discussed in Section 3.
4.1. BIOS CONFIGURATION
To protect information systems against physical security attacks, system administrators should
use up-to-data BIOS firmware and enable password protection to restrict unauthorized access to
BIOS configuration.
4.2. DISK ENCRYPTION
Attackers can bypass BIOS password protection by using a Dock Station. As a defender, to
prevent accessing file system without authorization, the entire hard drive should be encrypted by
applications such as BitLocker [57] by using hardware (such as TPM) protection.
4.3. NETWORK SEGMENTATION
Intrusion Detection Systems should be taken in place to detect and block network attacks and
anomalies on the corporate network. Computers should be separated into different networks
according to their security levels. For example, the following separation might be considered:
• Production, test and development servers
• Database and web application servers
• Clients and system admins
• Clients, internal servers and DMZ servers
should be separated into different networks.
4.4. SERVICE CONFIGURATION
Services that can be accessible from the public Internet increase attack surface. Therefore, system
administrators should ensure that all services are configured by taking all possible safety
precautions. First and foremost, unnecessary services should be disabled and all service accounts
should be removed from the computer.
4.5. PASSWORD SECURITY
Passwords are the last line of defence hackers. For this reason, brute-force password guessing
attacks and dictionary attacks can be effective on systems configured with easily predictable
password. Thus, system administrators should ensure that a secure password policy (minimum
length, complexity, change period, history, lockout, etc.) is applied via domain group policy [58].

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4.6. COUNTERMEASURES AGAINST PASS THE HASH ATTACK
To avoid pass the hash attack, all local admin accounts should have different passwords.
Unnecessary administrative shares, i.e. C:, $ADMIN, file and printer sharing should be disabled.
4.7. COUNTERMEASURES AGAINST CREDENTIAL THEFT ON MEMORY
Credential theft is one of the recent and important attacks. If possible, restrict privileged domain
user accounts to log on to workstations, otherwise logout these accounts after finishing the task.
All computers should be up-to-date systems and secured with endpoint protections.
4.8. COUNTERMEASURES AGAINST PASS THE TICKET (GOLDEN TICKET) ATTACKS
Monitoring domain controllers, especially unusual credential logons, should be considered.
4.9. BASIC CONTROLS AND HARDENINGS
System administrators should harden computers. For this reason, CIS [59], NIST [60] or
TUBITAK [61] guiding documents can be used for hardening and also companies can create
custom baselines to secure Windows OS.
4.10. UTILIZATION OF CRITICAL ACCOUNTS
System administrators should ensure the security of the domain critical groups such as enterprise
admins or domain admins. Monitoring group membership activities, different accounts on daily
tasks, delegated permissions should be considered.
4.11. PATCH MANAGEMENT
An effective patch management process can dramatically decrease attacks [62]. System
administrators, security assurance team and other related teams should define period,
prioritization and method of the patches by using a central patch management tool.
4.12. BACKUP MANAGEMENT
Nowadays, ransomwares increase the importance of the backups. System administrators should
define period, prioritization and method of the backups by using a central backup management
tool. Besides, it should not be forgotten the security of the backup files.
4.13. LOG MANAGEMENT AND MONITORING
Although there is security preventions, there is no 100% security. So it is very important to have
an effective log management. Collecting log is not enough; effective correlation rules and proper
alarms should be configured on the corporate network. Security operators should identify
systems, prioritization, storage and collecting method of the logs and alarms by using a central
log management tool. It should not be forgotten the security of the log files.
4.14. IDENTITY AND ACCESS MANAGEMENT
As workers periodically join and depart corporates and sometimes change their team security
team should define access control process to grant and revoke access to computing resources. To
this end, a central identity and access management tool can be used.
4.15. ACTIVE DIRECTORY AUDITS
Active Directory audits should be considered on Microsoft domain environment. At least, the
following audits can be performed:

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• Commonly used user accounts or service accounts
• User accounts that have not logged on for a while,
• User accounts having non-expire passwords,
• Disabled or departured users,
• User accounts that belong to 3rd parties,
• Membership of the critical users - such as Enterprise Admins, Domain Admins, Oracle
Admins, Network Admins-
• Empty groups or OUs.
4.16. INFORMATION SECURITY AWARENESS
Everyone - including system administrators, third-party vendors, visitors, janitors, senior
managers - on the corporate is responsible for the information security. Companies should
establish and maintain information security awareness programs and senior managers should give
adequate importance to information security.
4.17. Summary and ComparisonIn this study, we introduce a 10 step Microsoft Domain
penetration testing methodology called MSDEPTM. Each steps of MSDEPTM is presented as
rows in Table-1. In contrast, the countermeasures against these attacks discussed in Section 4 is
presented as columns in Table 1. Table 1 summarizes the mapping of the attacks and
countermeasures for Microsoft domain environment. As it is well-known fact backup
management provides preventative maintenance, 12th countermeasure (e.g. backup management)
is not matched with any attack step.
Table 1. Mapping of the Attacks and Mitigations For Microsoft Domain Environment
The Microsoft Domain Environment Penetration Testing Methodology (MSDEPTM) presented in
this research is compared with the state-of-the art studies (including standards, guidelines, or

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methodologies) in Table 2. After all, the proposed method is the only one focused on Windows
platform and discussed the attacks and their countermeasures in detail as well as the related
attacking tools. As shown in Table 2, the comparison of the methodologies is done according to
the following criteria.
• Owner: the owner of the specified methodology
• Last update time: the last update time of the methodology. Number of step / section: the
number of the step or section in the methodology
• Different techniques: Whether the specified methodology proposes different techniques.
• Scope: The scope of the methodology
• Countermeasures: Whether the methodology includes mitigations against attacks
• Tools: Whether the specified methodology recommends the tools for attacks.
Table 2. Comparison between MSDEPTM and the state of the art pentesting methodologies
5. CONCLUSION
In many corporations, the majority of their systems - servers and especially client computers - are
Microsoft. These systems are generally joined to Windows domain infrastructure to manage them
easily. System administrators should ensure that Windows domain environment is secured with
enough security precautions. Because, in case of a successful attack on the domain environment,
all of these systems can be compromised by cyber criminals.
In this paper, we proposed a Microsoft domain environment penetration testing methodology
called MSDEPTM. MSDEPTM presents the key metrics for penetration testing and describes the
fundamental steps of Microsoft domain environment attacks from the hacker point of view, root
causes of these attacks, and countermeasures against the attacks. We also compare our proposed
method with the other state of the art penetration testing methodologies for emphasizing our
contributions. We believe that the proposed methodology can help system admins and security
operators to build secure Windows environment.
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26
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27
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Authors
.
Abdurrahman Pektaş received his B.Sc. and M Sc. at Galatasaray
University and his PhD at the University of Joseph Fourier, all in
computer engineering, in 200 9, 2012 and 2015, respectively. He is a
senior researcher at Galatasaray University. His research interests are
analysis, detection and classification of malicious software, machine
learning and security analysis tool development.
Ertuğrul Başaranoğlu received his B.Sc. at Galatasaray University and
his in computer engineering at Istanbul Sehir University in 2010 and 2016,
respectively. He is senior penetration testing and security expert at Ziraat
Technology. His research interests are application security, reverse
engineering and penetration testing.

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