SEC505: Securing Windows with PowerShell and the Critical Security Controls
If you think you know Windows, take this Windows security class - your review of your own skills and understanding will be challenged, for the better!
Matthew Stoeckle, Nebraska Public Power District
You have the best instructors available. Other training never comes close and is a waste of money.
Steve Sauro, McDermott Will and Emery
SECURITY 505: Securing Windows with PowerShell and the Critical Security Controls
What is Windows Hello in Windows 10? How can we defend against pass-the-hash attacks, administrator account compromise, and the lateral movement of hackers inside our networks? How do we actually implement the Critical Security Controls on Windows in a large environment? We tackle these tough problems in SEC505: Securing Windows with PowerShell and the Critical Security Controls.
Understanding how penetration testers and hackers break into networks is not the same as knowing how to design defenses against them, especially when you work in a large and complex Active Directory environment. Knowing about tools like Metasploit, Cain, Netcat, and Poison Ivy is very useful, but there is no simple patch against the abuse of these tools. The goal of this course is to show you ways to defend against both current Windows attack techniques and the likely types of attacks we can expect in the future. This requires more than just reactive patch management - we need to proactively design security into our systems and networks. This course is like the defense-only mirror image of the SANS penetration testing course, SEC504, but for Windows only.
Your adversaries want to elevate their privileges to win control over your servers and domain controllers, so a major theme of this course is controlling administrative powers through Group Policy and PowerShell scripting.
Learning PowerShell is probably the single best new skill for Windows administrators, especially with the trend toward cloud computing. Most of your competition in the job market lacks scripting skills, so knowing PowerShell is a great way to make your resume stand out. This course devotes the entire first day to PowerShell, then we do more PowerShell exercises throughout the rest of the week. Don't worry, you don't need any prior scripting experience to attend.
SEC505 will also prepare you for the GIAC Certified Windows Security Administrator (GCWN) certification exam to prove your Windows security expertise. The GCWN certification counts toward getting a Master's Degree in information security from the SANS Technology Institute (www.sans.edu) and also satisfies the Department of Defense 8570 computing environment requirement.
This is a fun course and a real eye-opener, even for Windows administrators with years of experience. Come have fun learning PowerShell and Windows security!
Day 1: PowerShell Scripting
- New to scripting? No problem!
- PowerShell remoting
- Running cmdlets and scripts
- Writing your own functions and scripts
- Flow control within scripts
- Accessing COM and .NET objects
- Security and execution policy
Day 2: Operating System and Applications Hardening
- PowerShell and Windows Management Instrumentation (WMI)
- How your anti-virus scanners can fail you
- AppLocker whitelisting
- Microsoft EMET
- Windows OS and application hardening tools
- Group Policy Management Console (GPMC)
- INF and XML Security templates
- How to manage Group Policy
- WMI filtering and GPO preferences
- Virtual Desktop Infrastructure (VDI)
Day 3: High-Value Targets and Restricting Admin Compromise
- PowerShell for Active Directory
- What makes something a high-value target?
- Users in the local Administrators group
- Limiting privileges, logon rights, and permissions
- Windows Hello biometric authentication
- Token abuse and pass-the-hash attack mitigations
- User Account Control (UAC)
- Delegating IT power more safely
- Organizational units for role-based controls
- Active Directory permissions for delegation
- Active Directory auditing and logging
Day 4: Windows PKI, Smart Cards, and Managing Cryptography
- PowerShell for PKI
- Hardening SSL and TLS
- Why Public Key Infrastructure (PKI) is mandatory
- Examples: Smart Cards, VPNs, Wireless, SSL, S/MIME, etc.
- How to install and manage PKI
- Root vs. subordinate certification authorities
- Should you be your own root Certification Authority (CA)?
- Detecting malicious trusted CA changes with PowerShell
- Group policy deployment of certificates
- How to revoke certificates
- Automatic private key backup
- Deploying smart cards
- Best practices for private key security
Day 5: Server Hardening, IPSec, and Critical Protocols
- PowerShell for IPSec and firewall rules
- A recipe for hardening servers
- Dangerous protocols: SSL, RDP, IPv6, and SMB
- SMBv3 encryption and downgrade attacks
- Pre-forensics and incident response preparation
- Service accounts and recovery
- Scheduling elevated tasks safely
- Protocol stack hardening
- Kerberos armoring and restricting NTLM
- Server Nano versus Server Core
- Isn't IPSec just for VPNs? No!
- How to create IPSec policies
- Windows Firewall and IPSec integration
- Group Policy for IPSec and firewall rules
Day 6: Dynamic Access Control and Hardening DNS
- What is Dynamic Access Control (DAC)?
- DAC for data loss prevention
- DAC for complying with regulations
- PowerShell for DAC
- Automatic File Classification Infrastructure
- PowerShell for managing DNS
- DNSSEC response validation
- DNS secure dynamic updates
- DNS sinkholes for malware
You Will Learn:
- How to harden Windows clients and servers against attack.
- How to use PowerShell
- How to reduce the rate of APT malware infections.
- How to use PowerShell and Group Policy to manage security.
- How to implement PKI, AppLocker, IPSec, and more.
- How to do pre-forensics to prepare for incident response.
|SEC505.1: Windows PowerShell Scripting|
In the Windows world, everything is (thankfully) moving towards PowerShell. PowerShell is Microsoft's object-oriented command shell, scripting language, and remote management framework. Virtually everything can be managed from the command line now. Automation is very important for implementing the Critical Security Controls in large environments, so learning PowerShell is essential.
Today's course covers everything you need to know to get started using PowerShell. You don't need to have any prior scripting or programming experience. After today, we will look at PowerShell examples throughout the week as we work with our regular graphical tools to manage security. Ideally, we want to be able to manage security using either graphical tools or PowerShell (and usually both). In fact, some Microsoft graphical management tools are already built on top of PowerShell, and Microsoft is building more administrative tools this way.
As more and more of our systems are moved up to the cloud, PowerShell will become even more important. Microsoft Azure, Office 365, Amazon Web Services, Hyper-V and VMware already support PowerShell administration for many tasks. Learning PowerShell is a good investment in job security, too.
As a scripting language, PowerShell was specifically designed to be relatively easy to learn and immediately productive. You can quickly start doing very interesting things in PowerShell. Many attendees who feel anxious about writing code, perhaps after a bad experience with C/C++ or with another shell's strange syntax, are pleasantly surprised by how friendly PowerShell is to new coders. It was designed that way!
PowerShell is already built into Windows 7, Server 2008, and later operating systems. You can download sample scripts, documentation, and the latest version of PowerShell from http://www.microsoft.com/powershell/.
CPE/CMU Credits: 6
Overview and Security
Getting Around Inside PowerShell
Write Your Own Scripts
|SEC505.2: Windows Operating System and Applications Hardening|
The best analogy for modern network penetration is biological warfare. The hacker exploits a vulnerable client through weak software and social engineering in order to install malware. The malware opens an SSL command-and-control channel back to the attacker. This channel is used to control the initial "Typhoid Mary" computer to infect other vulnerable systems and exfiltrate (or destroy) valuable data. When you add stealth, self-updating features, worm-like mobility, and corporate/government sponsorship to the malware, you have an Advanced Persistent Threat (APT) situation. You are in trouble.
We do not just want to detect hackers and malware, we want to try to prevent the case-zero compromise from ever happening. Prevention comes first, then detection and remediation afterward. Today's course covers graphical and PowerShell tools that can be used to do Windows OS and applications hardening. The aim is to deny hackers and malware that initial foothold inside the network, because once they are in, they are hard to clean out.
The trick is hardening Windows in a way that is cost-effective, scalable, and has a minimal impact on users. We will look at tools like EMET and Group Policy to make that process easier. As throughout the week, today's section will also look at how to implement many of the Critical Security Controls.
The day begins with a continuation of the PowerShell material on the first day. In PowerShell, we will see how to interact with the Windows Management Instrumentation (WMI) service on remote computers. By talking to the WMI service, we can search event logs, start or stop processes, manage DNS records, reboot systems, and do hundreds of other tasks. PowerShell and WMI are tightly integrated, and learning WMI is very important for honing your PowerShell skills as a cyber-defense operator.
CPE/CMU Credits: 6
PowerShell and Windows Management Instrumentation (WMI)
Going Beyond Just Anti-Virus Scanning
OS Hardening with Security Templates
Hardening with Group Policy
|SEC505.3: High-Value Targets and Restricting Administrative Compromise|
If a member of the Domain Admins group is compromised, the entire network is lost. How can we better prevent the compromise of administrative accounts and contain the harm when they do get compromised? What can we do about pass-the-hash and token abuse attacks? Remember, as a network administrator, you are a high-value target and your adversaries will try to take over your user account and infect the computers you use at work (and at home).
Hackers also love it when "regular" users are members of the local Administrators group on their computers because it makes it easier to compromise those computers and then to move laterally to other machines. We will talk about what is so dangerous about the Administrators group, how to get users out of that group while still allowing them to get their work done, and, if we just cannot get users out of Administrators, then how to make User Account Control (UAC) less annoying to them...and to us.
We will also see how to delegate authority in Active Directory. Every object in Active Directory has a set of permissions and audit settings that we can leverage for security. Instead of simply adding everyone in the IT department to the Domain Admins group, we can more precisely delegate authority at the organizational unit level and grant limited powers to specific groups, such as the help desk or incident response groups.
Like almost everything else, Active Directory can be managed through PowerShell. In today's PowerShell section, we will see how to create, delete, and edit objects in Active Directory, such as user accounts and passwords. We will also see how to search Active Directory with any criteria we wish, like discovering all administrative accounts or listing those users with a large number of failed password attempts. PowerShell scripting of Active Directory is surprisingly easy and fun!
CPE/CMU Credits: 6
Compromise of Administrative Powers
PowerShell for Active Directory
Active Directory Permissions and Delegation
|SEC505.4: Windows PKI, Smart Cards, and Managing Cryptography|
Public Key Infrastructure (PKI) is not an optional security service anymore. Windows Server includes a complete built-in PKI for managing certificates and making their use transparent to users. You can be your own Certification Authority (CA) and generate as many certificates as you wish at no extra charge. It is all centrally managed through Group Policy and PowerShell.
Digital certificates play an essential role in Windows security: IPSec, BitLocker, S/MIME, SSL/TLS, smart cards, script signing, etc. all use digital certificates. Everything needed to roll out a smart card solution, for example, is included with Windows except for the cards and readers themselves, and generic cards are available in bulk for cheap. If you have a TPM chip in your laptop or tablet, it can actually be used as a built-in smart card too.
As more and more of our servers are pushed up to cloud hosting providers, and as more of our devices become mobile, certificate authentication and encryption will become more necessary. We are putting so much hope and trust into protocols like SSL and TLS, but these protocols are not perfect and have less-than-ideal default cipher settings on Windows. Hence, we will also talk about how to disable SSL, enable the latest version of TLS, eliminate weak ciphers, and maximize the cryptographic security of TLS. Because malware can inject fake root certification authority certificates into our machines, which subverts the authentication provided by TLS, we will also look at PowerShell scripts to audit and manage trusted root CA certificates on endpoints.
PowerShell management of PKI and cryptography can be a challenge, but there are tricks to making it easier. In this course, we will see how PowerShell can access certificates, audit our lists of trusted certification authorities, perform file hashing, and encrypt secret data, such as user passwords being sent over the wire. In fact, one of the scripts we use during the week does exactly that - it resets an administrator's password, the password is encrypted with our public key, and then sent securely over the network for archival. This sounds complex, but PowerShell makes it relatively easy.
CPE/CMU Credits: 6
Why Have Public Key Infrastructure?
How to Install the Windows PKI
How to Manage Your PKI
Deploying Smart Cards
|SEC505.5: Server Hardening, IPSec, and Critical Protocols|
What are the best practices for hardening Windows servers, especially servers exposed to the Internet? How can we remotely manage our servers in a secure way? If we have service accounts or scheduled jobs running as Domain Admin, what are the risks and what can we do about these risks? This part of the course is about server hardening.
IPSec is not just for VPNs. IPSec can authenticate users in Active Directory to implement share permissions for TCP and UDP ports based on the user's global group memberships. IPSec can also encrypt packet payloads to keep data secure. Imagine configuring the Windows Firewall on your servers and tablets to only permit access to your RPC or SMB ports if (1) the client has a local IP address, (2) the client is authenticated by IPSec to be a member of the domain, and (3) the packets are all encrypted with 256-bit AES. This is not only possible, it is actually relatively easy to deploy with Group Policy and can be scripted in PowerShell. This course section will show exactly how to do this.
For in-depth defense, we can no longer rely on just our perimeter firewalls. Many of our devices are mobile, so they are not protected by our perimeter firewalls anyway. You do not need to purchase third-party host-based firewalls like we did for Windows XP. The new Windows Firewall is a vast improvement and can be managed through Group Policy and PowerShell. For BYOD computers, the firewall and IPSec settings can also be scripted.
Are you using NTLM, Kerberos, Remote Desktop Protocol (RDP), or the File and Print Sharing protocol (SMB/CIFS)? These protocols and their listening ports are hacker favorites, but we cannot live without them, so we will see how to make these and other protocols more resilient against attacks. The cryptography we learned yesterday will help us better understand and harden the protocols in today's course section.
And, of course, IPSec policies, firewall rules, service account passwords, SMB encryption settings, etc. can almost always be scripted with PowerShell. We will see several PowerShell examples in today's course.
CPE/CMU Credits: 6
Creating IPSec Policies
Dangerous Server Protocols
|SEC505.6: Dynamic Access Control and Hardening DNS|
Windows Server 2012 introduced a major new security enhancement called Dynamic Access Control (DAC). If you have millions of files spread across multiple servers, how can you manage access to and auditing of these ever-changing files? How can we avoid relying on NTFS permissions and auditing alone?
DAC allows you to label files with such classifications as "Top Secret" or "PII," then apply restrictions and auditing based on these hidden file tags. But it is not done with AD group memberships and NTFS. DAC is not an NTFS management system, there is much more to it. With your own custom user and computer attributes defined in Active Directory, you can implement a Data Loss Prevention (DLP) solution based on "claims" associated with your users and their various devices. You can also perform auditing this way to help comply with regulations in your industry.
DAC works best with Server 2012 and Windows 8/10, but Windows 8/10 is not required. Even Windows XP clients can benefit. DAC is not just for file servers, either, it can also be extended to other platforms such as SharePoint, Rights Management Services (RMS), and Exchange. Finally, DAC is not a single tool or service, it is a new access control system with ties into the kernel.
Today's course also continues the server hardening theme from the previous day with coverage of DNS security. DNS is mandatory on our networks, but the protocol itself is horrible - hackers love it! There are several things we can do to make DNS less insecure. We can use DNSSEC to digitally signs DNS records to prevent spoofing and man-in-the-middle attacks, do DNS secure dynamic updates with Kerberos, set permissions on DNS records in Active Directory, use the DNS sinkhole technique to frustrate malware, and apply IPSec to DNS packets. DNS was not designed for security to begin with, so security has to be bolted on afterward.
Finally, it is no surprise that PowerShell can be used to manage DNS and Dynamic Access Control (DAC) settings. We will see plenty of examples, such as a PowerShell script for DNS sinkholing and PowerShell commands to manage DAC claims and file classifications.
CPE/CMU Credits: 6
Dynamic Access Control (DAC)
Please bring a virtual machine running an evaluation version Windows Server 2012 R2, Datacenter or Standard edition, installed with a full GUI (not Core). You will use the virtual machine throughout the week.
Here is a short video showing how to install your virtual machine.
Windows 8 and Windows 10, both Pro and Enterprise editions, include Client Hyper-V for running virtual machines. You can also obtain VMware Player for free. On a Mac, there is also VMware Fusion and Parallels.
Please note that if your laptop has an old CPU or less than 8GB of memory, you will be frustrated trying to keep up with the other attendees in the course. Please don't let your IT department spoil your experience by their giving you an old "loaner laptop" which is only used for training because it is so slow.
Your host computer must have a USB port or a USB adapter (the regular "Type-A" size used for USB flash drives).
The host computer can have any operating system because all of the labs are done in the guest virtual machine (and you must use a VM for the labs, not your host computer).
Where can I get the free evaluation version of Windows Server 2012 R2?
You can download a free trial version of Windows Server 2012 R2 from Microsoft as an ISO image file (an ISO file is an exported copy of a CD/DVD disk). Just do an Internet search on site:microsoft.com windows server trial eval to find the download link to the ISO file on Microsoft's web site.
Bring the ISO file with you on your hard drive when you attend the course.
How should my virtual machine be configured?
Other than simply creating the Windows Server virtual machine, there is nothing else to configure. Everything else will be done during the course.
Please install Windows Server 2012 R2 in your virtual machine. You can use either the Standard or Datacenter edition, either one works fine.
When you install the virtual machine, choose the "Server with a GUI" version of Windows Server, not the "Core" version. If you install the "Core" version, you will only get a CMD command shell when you log into the virtual machine. If you accidentally install the "Core" version, delete it and install a new virtual machine choosing the "Server with a GUI" option instead.
The virtual machine should not have network or Internet access, so configure the network interface of the virtual machine to be "host-only" or "private network" in your VM software. Do not apply any patches or updates.
Bring the ISO file with you on your hard drive when you attend the training.
If possible, configure your virtual machine to have two virtual CPUs. This helps to avoid error messages with some of the hacker tools used in the course. Your host laptop does not require two physical CPUs.
If your laptop can handle running two virtual machines simultaneously, then create a second identical virtual machine also running Windows Server. Having two virtual machines is not required for the course, it just makes some of the experimentation more fun (and is handy if there is a disaster).
VMware prompts me for a license number or I get a license error message! What should I do?
Make sure you have the evaluation version of Windows Server, not the retail version.
When creating the virtual machine in VMWare, it is best to choose the option that says "I will install the operating system later" and then provide the path to the ISO file for Windows Server after the virtual machine has been created, not during the initial creation. After the virtual machine has been created, go to the Settings of that virtual machine and provide the path to the source ISO file. Now, when you start the virtual machine, there should be no evaluation licensing problems.
If you have additional questions about the laptop specifications, please contact firstname.lastname@example.org.
|Who Should Attend|
There are no prerequisites to attend the course, but a familiarity with basic Windows and Active Directory concepts is presumed. You do not need any prior scripting experience.
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|What You Will Receive|
|You Will Be Able To|
|Press & Reviews|
"You will know and be confident how to enable Windows PKI after taking this course. I had no practical experience but plenty of theory. The instructor broke down the pros and cons of the whole process. Excellent!!" - Othello Swanston, DTRA-DOD
"If you think you know Windows, take this Windows security class - your review of your own skills and understanding will be challenged, for the better!!" - Matthew Stoeckle, Nebraska Public Power District