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CompTIA Security+ SY0-401 Authorized Cert Guide: OS Hardening and Virtualization

Out-of-the-box operating systems can often be insecure for a variety of reasons and need to be hardened to meet your organization’s policies, Trusted Operating System (TOS) compliance, and government regulations. But in general, they need to be hardened so that they are more difficult to compromise. This chapter focuses on the hardening of operating systems and the securing of virtual operating systems and will help you prepare for the CompTIA Security+ SY0-401 exam.
This chapter is from the book

This chapter covers the following subjects:

  • Hardening Operating Systems: Service packs, patches, hotfixes—This section details what you need to know to make your operating system strong as steel. Group policies, security templates, and baselining put on the finishing touches to attain that bullet-proof system.
  • Virtualization Technology: This section delves into virtual machines and other virtual implementations with an eye on applying real-world virtualization scenarios.

This chapter covers a portion of the CompTIA Security+ SY0-401 objectives 3.6, 4.1, and 4.3.

Imagine a computer with a freshly installed server operating system (OS) placed on the Internet or on a DMZ that went live without any updating, service packs, or hotfixes. How long do you think it would take for this computer to be compromised? A week? Sooner? It depends on the size and popularity of the organization, but it won’t take long for a nonhardened server to be compromised. And it’s not just servers! Workstations, routers, switches: You name it; they all need to be updated regularly, or they will fall victim to attack. By updating systems frequently and by employing other methods such as group policies and baselining, we are hardening the system, making it tough enough to withstand the pounding that it will probably take from today’s technology...and society.

Another way to create a secure environment is to run operating systems virtually. Virtual systems allow for a high degree of security, portability, and ease of use. However, they are resource-intensive, so a balance needs to be found, and virtualization needs to be used according to the level of resources in an organization. Of course, these systems need to be maintained and updated (hardened) as well.

By utilizing virtualization properly and by implementing an intelligent update plan, operating systems, and the relationships between operating systems, can be more secure and last a long time.

Foundation Topics

Hardening Operating Systems

An operating system, or OS, that has been installed out-of-the-box is inherently insecure. This can be attributed to several things, including initial code issues and backdoors, the age of the product, and the fact that most systems start off with a basic and insecure set of rules and policies. How many times have you heard of a default OS installation where the controlling user account was easily accessible and had no password? Although these types of oversights are constantly being improved upon, making an out-of-the-box experience more pleasant, new applications and new technologies offer new security implications as well. So regardless of the product, we must try to protect it after the installation is complete.

Hardening of the OS is the act of configuring an OS securely, updating it, creating rules and policies to help govern the system in a secure manner, and removing unnecessary applications and services. This is done to minimize OS exposure to threats and to mitigate possible risk. Although it is impossible to reduce risk to zero, I’ll show some tips and tricks that can enable you to diminish current and future risk to an acceptable level.

This section demonstrates how to harden the OS through the use of service packs, patches and patch management, hotfixes, group policies, security templates, and configuration baselines. We then discuss a little bit about how to secure the file system and hard drives. But first, let’s discuss how to analyze the system and decide which applications and services are unnecessary, and then remove them.

Removing Unnecessary Applications and Services

Unnecessary applications and services use valuable hard drive space and processing power. Plus, they can be vulnerabilities to an operating system.

For example, instant messaging programs might be fun for a user but usually are not productive in the workplace (to put it nicely); plus, they often have backdoors that are easily accessible to attackers. They should be discouraged or disallowed by rules and policies. Be proactive when it comes to these types of programs. If users can’t install an IM program on their computer, you will never have to remove it from the system. But if you do have to remove an application like this, be sure to remove all traces that it ever existed. Make sure that related services are turned off and disabled. Then verify that their inbound ports are no longer functional, and that they are closed and secured. For example, AOL Instant Messenger (AIM) uses inbound port 5190, which is well known to attackers, as are other inbound ports of other IM programs, such as ICQ or Trillian. Confirm that any shares created by an application are disabled as well. Basically, remove all instances of the application or, if necessary, re-image the computer! That is just one example of many, but it can be applied to most superfluous programs. Another type of program you should watch out for are remote control programs. Applications that enable remote control of a computer should be avoided if possible.

Personally, I use a lot of programs. But over time, some of them fall by the wayside and are replaced by better programs. The best procedure is to check a system periodically for any unnecessary programs. For example, in Windows 7 we can look at the list of installed programs by going to the Control Panel > Programs > Programs and Features, as shown in Figure 3-1.

Figure 3-1

Figure 3-1 Windows 7 Programs and Features Window

Notice in the figure that Camtasia Studio 5 is installed. This is an older version of the program. If in the future I decide to install the latest version of Camtasia, or use another program, such as Adobe Captivate or something similar, and Camtasia 5 is no longer necessary, then it should be removed. This can be done by right-clicking the application and selecting Uninstall. Or an application might have an uninstall feature built into the Start menu that you can use. Programs such as this can use up to 50 MB, 100 MB, and possibly much more, so it makes sense to remove them to conserve hard drive space. This becomes more important when you deal with audio/video departments that would use an application such as Camtasia, and most likely many others like it. The applications are always battling for hard drive space, and it can get ugly! Not only that, but many applications place a piece of themselves in the Notification Area in Windows. So, a part of the program is actually running behind the scenes using processor/RAM resources. If the application is necessary, there are often ways to eliminate it from the Notification Area, either by right-clicking it and accessing its properties, or by turning it off with a configuration program such as the System Configuration Utility in Windows (which can be executed by going to Start > Run and typing msconfig).

Consider also that apps like this might also attempt to communicate with the Internet in an attempt to download updates, or for other reasons. It makes this issue not only a resource problem, but also a security concern, so it should be removed if it is unused. Only software deemed necessary should be installed in the future.

Now, uninstalling applications on a few computers is feasible, but what if you have a larger network? Say, one with 1,000 computers? You can’t expect yourself or your computer techs to go to each and every computer locally and remove applications. That’s when centrally administered management systems come into play. Examples of these include Microsoft’s System Center Configuration Manager (SCCM), and the variety of mobile device management suites available. These programs allow a security administrator to manage lots of computers’ software, configurations, and policies, all from the local workstation.

Of course, it can still be difficult to remove all the superfluous applications from every end-user computer on the network. What’s important to realize here is that applications are at their most dangerous when actually being used by a person. Given this mindset, you should consider the concept of application whitelisting and blacklisting. Application whitelisting, as mentioned in Chapter 2, “Computer Systems Security,” is when you set a policy that allows only certain applications to run on client computers (such as Microsoft Word and Internet Explorer). Any other application will be denied to the user. This works well in that it eliminates any possibility (excluding hacking) of another program being opened by an end user, but it can cause productivity problems. When an end user really needs another application, an exception would have to be made to the rule for that user, which takes time, and possibly permission from management. Application blacklisting, on the other hand, is when individual applications are disallowed. This can be a more useful (and more efficient) solution if your end users work with, and frequently add, a lot of applications. In this scenario, an individual application (say a social media or chat program) is disabled across the network. This and whitelisting are often performed from centralized management systems mentioned previously, and through the use of policies, which we discuss more later in this chapter (and later in the book).

Services are used by applications and the OS. They too can be a burden on system resources and pose security concerns. Examine Figure 3-2 and note the highlighted service.

Figure 3-2

Figure 3-2 Services Window in Windows XP

The OS shown in Figure 3-2 is Windows XP. Normally, I wouldn’t use Windows XP as an example given its age (and the fact that Microsoft will not support it anymore), but in this case I must because of the insecure nature of Telnet and the numerous systems that will probably continue to run Windows XP for some time. Windows XP was the last Microsoft OS to have Telnet installed by default, even though it was already well known that Telnet was a security risk. This is an example of an out-of-the-box security risk. But to make matters worse, the Telnet service in the figure is started! Instead of using Telnet, a more secure application/protocol should be utilized such as SSH. Then Telnet should be stopped and disabled. To do so, just right-click the service, select Properties, click the Stop button, and change the Startup Type drop-down menu to the Disabled option, as shown in Figure 3-3.

Figure 3-3

Figure 3-3 Telnet Properties Dialog Box

This should be done for all unnecessary services, for example, the Trivial File Transfer Protocol (TFTP). By disabling services such as this one, we can reduce the risk of attacker access to the computer and we trim the amount of resources used. This is especially important on Windows servers, because they run a lot more services and are a more common target. By disabling unnecessary services, we reduce the size of the attack surface.

Services can be started and stopped in the Windows Command Prompt with the net start and net stop commands, as well as by using the sc command. Examples of this are shown in Figure 3-4.

Figure 3-4

Figure 3-4 Stopping and Disabling a Service in the Windows 7 Command Prompt

In Figure 3-4 we have stopped and started the Windows Firewall service (which uses the service name mpssvc) by invoking the net stop and net start commands. Then, we used the sc command to stop the same service with the sc stop mpssvc syntax. It shows that the service stoppage was pending, but as you can see from Figure 3-5, it indeed stopped (and right away, I might add). Finally, we used a derivative of the sc command to disable the service, so that it won’t start again when the system is restarted. This syntax is

sc config mpssvc start= disabled
Figure 3-5

Figure 3-5 Windows Firewall Properties Dialog Box

Note that there is a space after the equal sign, which is necessary for the command to work properly. Figure 3-5 shows the GUI representation of the Windows Firewall service.

You can see in the figure that the service is disabled and stopped. This is a good place to find out the name of a service if you are not sure. Or, you could use the sc query command.

In Linux, you can start, stop, and restart services in a variety of ways. Because there are many variants of Linux, how you perform these actions varies in the different GUIs that are available. So, in this book I usually stick with the command-line, which is generally the same across the board. You’ll probably want to display a list of services (and their status) in the command-line first. For example, in Ubuntu you can do this by typing the following:

service --status all

For a list of upstart jobs with their status, use the following syntax:

initctl list

Services can be stopped in the Linux command-line in a few ways:

  • By typing the following syntax:

    /etc/init.d/<service> stop

    where <service> is the service name. For example, if you are running an Apache web server, you would type the following:

    /etc/init.d/apache2 stop

    Services can also be started and restarted by replacing stop with start or restart.

  • By typing the following syntax in select versions:

    service <service> stop

Some services require a different set of syntax. For example, Telnet can be deactivated in Red Hat by typing chkconfig telnet off. Check the MAN pages within the command-line or online for your particular version of Linux to obtain exact syntax and any previous commands that need to be issued. Or use a generic Linux online MAN page; for example: http://linux.die.net/man/1/telnet.

In OS X Server, services can be stopped in the command-line by using the following syntax:

sudo serveradmin stop <service>

However, this doesn’t work on OS X client. In OS X client (for example, 10.9 Mavericks) you would simply quit processes either by using the Activity Monitor or by using the kill command in the Terminal.

Table 3-1 summarizes the various ways to stop services in operating systems.


Table 3-1 Summary of Ways to Stop Services

Operating System

Procedure to Stop Service


Access services.msc from the Run prompt.

Use the net stop <servicename> command in the Command Prompt.

Use the sc stop <servicename> command in the Command Prompt.


Use the syntax /etc/init.d/<servicename> stop.

Use the syntax service <servicename> stop (in select versions).

Use the syntax chkconfig <servicename> off (in select versions).


Use the kill command to end processes. Also works in Linux. In Windows, this is the taskkill command.

Don’t confuse services with service packs. Although a service controls a specific function of an OS or application, a service pack is used to update a system. The service pack probably will update services as well, but the similarity in names is purely coincidental.

Service Packs

A service pack (SP) is a Microsoft-centric group of updates, bug fixes, updated drivers, and security fixes installed from one downloadable package or from one disc. When the number of patches for an OS reaches a certain limit, they are gathered together into an SP. This might take one to several months after the OS is released. Because organizations know an SP will follow an OS release, which implies that there will be security issues with a brand-new out-of-the-box OS, they will usually wait until the first SP is released before embracing a new OS.

SPs are numbered; for example SP1, SP2, and so on. An OS without an SP is referred to as SP0. Installing an SP is relatively easy and only asks a few basic questions. When those questions are answered, it takes several minutes or more to complete the update; then a restart is required. Although the SP is installed, it rewrites many files and copies new ones to the hard drive as well.

Historically, many SPs have been cumulative, meaning that they also contain previous SPs. But in some cases they have to be installed individually. For example, with Windows Vista, SP1 must be installed before updating to SP2. Before installing an SP, read the instructions that accompany it, or the instructions on the download page on the company’s website.

To find out an OS’s current SP level, click Start, right-click Computer, and select Properties, and the SP should be listed. If there is no SP installed, it will be blank. An example of Windows 7’s System window is shown in Figure 3-6; it shows that SP1 is installed. Windows Server operating systems work in the same fashion.

Figure 3-6

Figure 3-6 Windows 7 System Window

You can also find out which service pack your operating system uses by opening the System Information tool (open the Run prompt and type msinfo32.exe). It will be listed directly in the system summary. In addition, you can use the systeminfo command in the Command Prompt (a GREAT information gatherer!).

Another tool you can use to find out the SP level besides msinfo32.exe is the winver command. This can be run in the Run prompt, in the search box, or in the Command Prompt. Either way, it will bring up the About Windows window. You can also discern SP levels directly in the Command Prompt. For example, if you open the Command Prompt in Windows 7 and see on the top line Microsoft Windows [Version 6.1.7600], then no SP is installed. But if you do this on Windows 7 with SP1, you will see Microsoft Windows [Version 6.1.7601]. Note the difference in the last number. You can also see this by simply typing ver. You can also find out the OS name, version, and SP level with the following syntax:

systeminfo|findstr /B /C:"OS Name" /C:"OS Version"

Note the pipe symbol between systeminfo and findstr. Also, the text within the quotes is case sensitive.

In this example, the resulting output on a Windows 7 Ultimate OS with SP1 installed would be

OS Name: Microsoft Windows 7 Ultimate
OS Version: 6.1.7601 Service Pack 1 Build 7601

For the Version/SP level only, omit the following:

/C:"OS Name"

To find out which SP a particular version of Office is running, click Help on the menu bar and select About Microsoft Office <Application Name>, where the application name could be Outlook, Word, and so on, depending on what app you use. Service packs are also used by Windows Server products and add-on products to Windows Server such as Microsoft Exchange Server.

SPs can be acquired through Windows Update, at www.microsoft.com, on disc, and through a Microsoft Developer Network (MSDN) subscription. An SP might also have been incorporated into the original OS distribution disc. This is known as slipstreaming. This method enables the user to install the OS and the SP at the same time in a seamless manner. System administrators can create slipstreamed images for simplified over-the-network installations of the OS and SP.

If possible, the testing of service packs should be done offline (with physical media). Disconnect the computer from the network by disabling the network adapter before initiating the SP upgrade. Again, because brand-new operating systems are inherently insecure to some extent (no matter what a manufacturer might say), organizations usually wait for the release of the first SP before implementing the new OS on a live network. However, SPs are not the only type of updating you need to do to your computers. Microsoft operating systems require further patching with the Windows Update program, and other applications require their own patches and hotfixes.

Windows Update, Patches, and Hotfixes

To be considered secure, operating systems should have support for multilevel security, and be able to meet government requirements. An operating system that meets these criteria is known as a Trusted Operating System (TOS). Examples of this include Windows 7, OS X 10.6, FreeBSD (with the TrustedBSD extensions), and Red Hat Enterprise Server. To be considered a TOS, the manufacturer of the system must have strong policies concerning updates and patching.

Even without being a TOS, operating systems should be updated regularly. For example, Microsoft recognizes the deficiencies in an OS, and possible exploits that could occur, and releases patches to increase OS performance and protect the system. After the latest SP has been installed, the next step is to see whether any additional updates are available for download.

For example, if you want to install additional updates for Windows 7 through Windows Update, choose Start > All Programs > Windows Update, and click Check for Updates in the left panel. The system then automatically scans for updates. Updates are divided into the following categories:

  • Critical updates and SPs: Include the latest SP and other security and stability updates. Some updates must be installed individually; others can be installed as a group.
  • Windows updates: Recommended updates to fix noncritical problems certain users might encounter; also adds features and updates to features bundled into Windows.
  • Driver updates: Updated device drivers for installed hardware.

If your system is in need of updates, a shield (for the Windows Security Center) appears in the Notification Area. Double-clicking this brings up the Security Center window in which you can turn on automatic updates. To modify how you are alerted to updates, and how they are downloaded and installed in Windows 7, choose Start > All Programs > Windows Update and then click the Change Settings link.

From here, there will be four options (in other operating systems, the options might be slightly different):

  • Install Updates Automatically: This is the option recommended by Microsoft. You can schedule when and how often the updates should be downloaded and installed.
  • Download Updates but Let Me Choose Whether to Install Them: This automatically downloads updates when they become available, but Windows prompts you to install them instead of installing them automatically. Each update has a checkbox, so you can select individual updates to install.
  • Check for Updates but Let Me Choose Whether to Download and Install Them: This enables you to know when updates are available, but you are in control as to when they are downloaded and installed.
  • Never Check for Updates: This is not recommended by Microsoft because it can be a security risk, but it might be necessary in some environments in which updates could cause conflicts over the network. In some networks, the administrator takes care of updates from a server and sets the local computers to this option.
Patches and Hotfixes

The best place to obtain patches and hotfixes is from the manufacturer’s website. The terms patches and hotfixes are often used interchangeably. Windows Updates are made up of hotfixes. Originally, a hotfix was defined as a single problem-fixing patch to an individual OS or application installed live while the system was up and running and without a reboot necessary. However, this term has changed over time and varies from vendor to vendor. (Vendors may even use both terms to describe the same thing.) For example, if you run the systeminfo command in the Command Prompt of a Windows Vista computer, you see a list of Hotfix(es), similar to Figure 3-7. The figure doesn’t show all of them because there are 88 in total. However, they can be identified with the letters KB followed by six numbers. Some of these are single patches to individual applications, but others affect the entire system, such as #88, which is called KB948465. This hotfix is actually Windows Vista Service Pack 2!—which includes program compatibility changes, additional hardware support, and general OS updates. And a Service Pack 2 installation definitely requires a restart.

Figure 3-7

Figure 3-7 Running the systeminfo Command in Windows

On the other side of the spectrum, Blizzard Entertainment defines hotfixes in its World of Warcraft game as a “hot” change to the server with no downtime (or a quick world restart), and no client download is necessary. The organization releases these if they are critical, instead of waiting for a full patch version. The gaming world commonly uses the terms patch version, point release, or maintenance release to describe a group of file updates to a particular gaming version. For example, a game might start at version 1 and later release an update known as 1.17. The .17 is the point release. (This could be any number, depending on the amount of code rewrites.) Later, the game might release 1.32, in which .32 is the point release, again otherwise referred to as the patch version. This is common with other programs as well. For example, the aforementioned Camtasia program that is running on the computer shown in Figure 3-1 is version 5.0.2. The second dot (.2) represents very small changes to the program, whereas a patch version called 5.1 would be a larger change, and 6.0 would be a completely new version of the software. This concept also applies to blogging applications and forums (otherwise known as bulletin boards). As new threats are discovered (and they are extremely common in the blogging world), new patch versions are released. They should be downloaded by the administrator, tested, and installed without delay. Admins should keep in touch with their software manufacturers, either through phone or e-mail, or by frequenting their web pages. This keeps the admin “in the know” when it comes to the latest updates. And this applies to server and client operating systems, server add-ons such as Microsoft Exchange or SQL Server, Office programs, web browsers, and the plethora of third-party programs that an organization might use. Your job just got a bit busier!

Of course, we are usually not concerned with updating games in the working world; they should be removed from a computer if they are found (unless perhaps you work for a gaming company). But multimedia software such as Camtasia is prevalent in most companies, and web-based software such as bulletin-board systems are also common and susceptible to attack.

Patches generally carry the connotation of a small fix in the mind of the user or system administrator, so larger patches are often referred to as software updates, service packs, or something similar. However, if you were asked to fix a single security issue on a computer, a patch would be the solution you would want. For example, there are various Trojans that attack older versions of Microsoft Office for Mac. To counter these, Microsoft released a specific patch for those versions of Office for Mac that disallows remote access by the Trojans.

Before installing an individual patch, you should determine if it perhaps was already installed as part of a group update. For example, you might read that OS X 10.8 had a patch released for iTunes, and being an enthusiastic iTunes user, you might consider installing the patch. But you should first find out the version of the OS you are running. For example, Figure 3-8 shows a Mac that runs OS X version 10.9.1. That would most likely include the earlier patch for iTunes. To find this information, simply click the Apple menu and then click About This Mac.

Figure 3-8

Figure 3-8 OS X Version Number

Sometimes, patches are designed poorly, and although they might fix one problem, they could possibly create another, which is a form of software regression. Because you never know exactly what a patch to a system might do, or how it might react or interact with other systems, it is wise to incorporate patch management.

Patch Management

It is not wise to go running around the network randomly updating computers, not to say that you would do so! Patching, like any other process, should be managed properly. Patch management is the planning, testing, implementing, and auditing of patches. Now, these four steps are ones that I use; other companies might have a slightly different patch management strategy, but each of the four concepts should be included:

  • Planning: Before actually doing anything, a plan should be set into motion. The first thing that needs to be decided is whether the patch is necessary and whether it is compatible with other systems. Microsoft Baseline Security Analyzer (MBSA) is one example of a program that can identify security misconfigurations on the computers in your network, letting you know whether patching is needed. If the patch is deemed necessary, the plan should consist of a way to test the patch in a “clean” network on clean systems, how and when the patch will be implemented, and how the patch will be checked after it is installed.
  • Testing: Before automating the deployment of a patch among a thousand computers, it makes sense to test it on a single system or small group of systems first. These systems should be reserved for testing purposes only and should not be used by “civilians” or regular users on the network. I know, this is asking a lot, especially given the amount of resources some companies have. But the more you can push for at least a single testing system that is not a part of the main network, the less you will be to blame if a failure occurs!
  • Implementing: If the test is successful, the patch should be deployed to all the necessary systems. In many cases this is done in the evening or over the weekend for larger updates. Patches can be deployed automatically using software such as Microsoft’s System Center Configuration Manager (SCCM) or the older Systems Management Server (SMS).
  • Auditing: When the implementation is complete, the systems (or at least a sample of systems) should be audited; first, to make sure the patch has taken hold properly, and second, to check for any changes or failures due to the patch. SCCM, SMS, and other third-party tools can be used in this endeavor.

There are also Linux-based and Mac-based programs and services developed to help manage patching and the auditing of patches. Red Hat has services to help sys admins with all the RPMs they need to download and install, which can become a mountain of work quickly! And for those people who run GPL Linux, there are third-party services as well. A network with a lot of mobile devices benefits greatly from the use of a mobile device management (MDM) platform. But even with all these tools at an organization’s disposal, sometimes, patch management is just too much for one person, or for an entire IT department, and an organization might opt to contract that work out.

Although they are important tasks, removing applications, disabling services, patching, hotfixing, and installing service packs are not the only ways to harden an operating system. Administrative privileges should be used sparingly, and policies should be in place to enforce your organization’s rules. A Group Policy is used in Microsoft and other computing environments to govern user and computer accounts through a set of rules. Built-in or administrator-designed security templates can be applied to these to configure many rules at one time. Afterward, configuration baselines should be created and used to measure server and network activity.

To access the Group Policy in Windows, go to the Run prompt and type gpedit.msc. This should display the Local Group Policy Editor console window. Figure 3-9 shows an example of this in Windows 7.

Figure 3-9

Figure 3-9 Local Group Policy Editor in Windows 7

Although there are many configuration changes you can make, this figure focuses on the computer’s security settings that can be accessed by navigating to Local Computer Policy > Computer Configuration > Windows Settings > Security Settings. From here you can make changes to the password policies (for example, how long a password lasts before having to be changed), account lockout policies, public key policies, and so on. We talk about these different types of policies and the best way to apply them in future chapters. The Group Policy Editor in the figure is known as the Local Group Policy Editor and only governs that particular machine and the local users of that machine. It is a basic version of the Group Policy Editor used by Windows Server domain controllers that have Active Directory loaded.

It is also from here that you can add security templates as well. Security templates are groups of policies that can be loaded in one procedure; they are commonly used in corporate environments. Different security templates have different security levels. These can be installed by right-clicking Security Settings and selecting Import Policy. This brings up the Import Policy From window. This technique of adding a policy template becomes much more important on Windows Server computers. Figure 3-10 shows an example of the Import Policy From window in Windows Server 2012.

Figure 3-10

Figure 3-10 Windows Server 2012 Import Policy From Window

There are three main security templates in Server 2012/2008: defltbase.inf (uncommon), defltsv.inf (used on regular servers), and defltdc.inf (used in domain controllers). By default, these templates are stored in %systemroot%\inf (among a lot of other .inf files).

Select the policy you desire and click Open. That establishes the policy on the server. It’s actually many policies that are written to many locations of the entire Local Security Policy window. Often, these policy templates are applied to organizational units on a domain controller. But they can be used for other types of systems and policies as well.

In Server 2012 you can modify policies, and add templates, directly from Server Manager > Security Configuration Wizard as well. If you save templates here, they are saved as .xml files instead of .inf files.

Group Policies are loaded with different Group Policy objects (GPOs). By configuring as many of these GPOs as possible, you implement OS hardening, ultimately establishing host-based security for your organization’s workstations.

Baselining is the process of measuring changes in networking, hardware, software, and so on. Creating a baseline consists of selecting something to measure and measuring it consistently for a period of time. For example, I might want to know what the average hourly data transfer is to and from a server. There are many ways to measure this, but I could possibly use a protocol analyzer to find out how many packets cross through the server’s network adapter. This could be run for 1 hour (during business hours of course) every day for 2 weeks. Selecting different hours for each day would add more randomness to the final results. By averaging the results together, we get a baseline. Then we can compare future measurements of the server to the baseline. This can help us to define what the standard load of our server is and the requirements our server needs on a consistent basis. It can also help when installing additional computers on the network. The term baselining is most often used to refer to monitoring network performance, but it actually can be used to describe just about any type of performance monitoring. Baselining and benchmarking are extremely important when testing equipment and when monitoring already installed devices. We discuss this further in Chapter 12, “Monitoring and Auditing.”

Hardening File Systems and Hard Drives

You want more? I promise more. The rest of the book constantly refers to more advanced and in-depth ways to harden a computer system. But for this chapter, let’s conclude this section by giving a few tips on hardening a hard drive and the file system it houses.

First, the file system used dictates a certain level of security. On Microsoft computers, the best option is to use NTFS, which is more secure, enables logging (oh so important), supports encryption, and has support for a much larger maximum partition size and larger file sizes. Just about the only place where FAT32 and NTFS are on a level playing field is that they support the same amount of file formats. So, by far, NTFS is the best option. If a volume uses FAT or FAT32, it can be converted to NTFS using the following command:

convert volume /FS:NTFS

For example, if I want to convert a USB flash drive named M: to NTFS, the syntax would be

convert M: /FS:NTFS

There are additional options for the convert command. To see these, simply type convert /? in the Command Prompt. NTFS enables for file-level security and tracks permissions within access control lists (ACLs), which are a necessity in today’s environment. Most systems today already use NTFS, but you never know about flash-based and other removable media. A quick chkdsk command in the Command Prompt or right-clicking the drive in the GUI and selecting Properties can tell you what type of file system it runs.

Generally, the best file system for Linux systems is ext4. It allows for the best and most configurable security. To find out the file system used by your version of Linux, use the fdisk –l command or df –T command.

System files and folders by default are hidden from view to protect a Windows system, but you never know. To permanently configure the system to not show hidden files and folders, navigate to Windows Explorer or File Explorer, click the Tools menu, and click Folder Options. Then select the View tab, and under Hidden Files and Folders select the Do Not Show Hidden Files and Folders radio button. Note that in newer versions of Windows, the menu bar can also be hidden; to view it, press Alt+T on the keyboard. To configure the system to hide protected system files, select the Hide Protected Operating System Files checkbox, located three lines below the radio button previously mentioned. This disables the ability to view such files and folders as bootmgr, boot, ntldr, and boot.ini. You might also need to secure a system by turning off file sharing. For example, this can be done in Windows 7 within the Network and Sharing Center, and within Windows XP in the Local Area Connection Properties dialog box.

In the past, I have made a bold statement: “Hard disks will fail.” But it’s all too true. It’s not a matter of if; it’s a matter of when. By maintaining and hardening the hard disk with various hard disk utilities, we attempt to stave off that dark day as long as possible. You can implement several things when maintaining and hardening a hard disk:

  • Remove temporary files: Temporary files and older files can clog up a hard disk, cause a decrease in performance, and pose a security threat. It is recommended that Disk Cleanup or a similar program be used. Policies can be configured (or written) to run Disk Cleanup every day or at logoff for all the computers on the network.
  • Periodically check system files: Every once in a while it’s a good idea to verify the integrity of operating system files. This can be done in the following ways:

    • With the chkdsk command in Windows. This checks the disk and fixes basic issues such as lost files, and some errors with the /F option.
    • With the SFC (System File Checker) command in Windows. This utility checks and, if necessary, replaces protected system files. It can be used to fix problems in the OS, and in other applications such as Internet Explorer. A typical command you might type is SFC /scannow. Use this if chkdsk is not successful at making repairs.
    • With the fsck command in Linux. This command is used to check and repair a Linux file system. The synopsis of the syntax is fsck [ -sAVRTNP ] [ -C [ fd ] ] [ -t fstype ] [filesys ... ] [--] [ fs-specific-options ]. More information about this command can be found at the corresponding MAN page for fsck. A derivative, e2fsck, is used to check a Linux ext2fs (second extended file system). Also, open source data integrity tools can be downloaded for Linux such as Tripwire.
  • Defragment drives: Applications and files on hard drives become fragmented over time. For a server, this could be a disaster, because the server cannot serve requests in a timely fashion if the drive is too thoroughly fragmented. Defragmenting the drive can be done with Microsoft’s Disk Defragmenter, with the command-line defrag command, or with other third-party programs.
  • Back up data: Backing up data is critical for a company. It is not enough to rely on a fault-tolerant array. Individual files or the entire system can be backed up to another set of hard drives, to optical discs, to tape, or to the cloud. Microsoft domain controllers’ Active Directory databases are particularly susceptible to attack; the System State for these operating systems should be backed up, in case that the server fails and the Active Directory needs to be recovered in the future.
  • Use restoration techniques: In Windows, restore points should be created on a regular basis for servers and workstations. The System Restore utility (rstrui.exe) can fix issues caused by defective hardware or software by reverting back to an earlier time. Registry changes made by hardware or software are reversed in an attempt to force the computer to work the way it did previously. Restore points can be created manually and are also created automatically by the OS before new applications, service packs, or hardware are installed. OS X uses the Time Machine utility, which works in a similar manner. Though there is no similar tool in Linux, a user can back up the ~/home directory to a separate partition. When these contents are decompressed to a new install, most of the Linux system and settings will have been restored. Another option in general is to use imaging (cloning) software such as Acronis True Image, Paragon Hard Disk Manager, or PowerISO. Remember that these techniques do not necessarily back up data, and that the data should be treated as a separate entity that needs to be backed up regularly.
  • Consider whole disk encryption: Finally, whole disk encryption can be used to secure the contents of the drive, making it harder for attackers to obtain and interpret its contents.

A recommendation I give to all my students and readers is to separate the OS from the data physically. If you can have each on a separate hard drive, it can make things a bit easier just in case the OS is infected with malware (or otherwise fails). The hard drive that the OS inhabits can be completely wiped and reinstalled without worrying about data loss, and applications can always be reloaded. Of course, settings should be backed up (or stored on the second drive). If a second drive isn’t available, consider configuring the one hard drive as two partitions, one for the OS (or system) and one for the data. By doing this, and keeping a well-maintained computer, you are effectively hardening the OS.


Virtualization Technology

Let’s define virtualization. Virtualization is the creation of a virtual entity, as opposed to a true or actual entity. The most common type of entity created through virtualization is the virtual machine—usually as an OS. In this section we discuss types of virtualization, identify their purposes, and define some of the various virtual applications.

Types of Virtualization and Their Purposes

Many types of virtualization exist, from network and storage to hardware and software. The CompTIA Security+ exam focuses mostly on virtual machine software. The virtual machines (VMs) created by this software run operating systems or individual applications. These virtual operating systems (also known as hosted operating systems or guests) are designed to run inside a real OS. So the beauty behind this is that you can run multiple various operating systems simultaneously from just one PC. This has great advantages for programmers, developers, and systems administrators, and can facilitate a great testing environment. Security researchers in particular utilize virtual machines so they can execute and test malware without risk to an actual OS and the hardware it resides on. Nowadays, many VMs are also used in live production environments. Plus, an entire OS can be dropped onto a DVD or even a flash drive and transported where you want to go.

Of course, there are drawbacks. Processor and RAM resources and hard drive space are eaten up by virtual machines. And hardware compatibility can pose some problems as well. Also, if the physical computer that houses the virtual OS fails, the virtual OS will go offline immediately. All other virtual computers that run on that physical system will also go offline. There is added administration as well. Some technicians forget that virtual machines need to be updated with the latest service packs and patches just like regular operating systems. Many organizations have policies that define standardized virtual images, especially for servers. As I alluded to earlier, the main benefit of having a standardized server image is that mandated security configurations will have been made to the OS from the beginning—creating a template, so to speak. This includes a defined set of security updates, service packs, patches, and so on, as dictated by organizational policy. So when you load up a new instance of the image, a lot of the configuration work will already have been done, and just the latest updates to the OS and AV software need to be applied. This image can be used in a virtual environment, or copied to a physical hard drive as well. For example, you might have a server farm that includes two physical Windows Server systems and four virtual Windows Server systems, each running different tasks. It stands to reason that you will be working with new images from time to time as you need to replace servers or add them. By creating a standardized image once, and using it many times afterward, you can save yourself a lot of configuration time in the long run.

Virtual machines can be broken down into two categories:

  • System virtual machine: A complete platform meant to take the place of an entire computer, enabling you to run an entire OS virtually.
  • Process virtual machine: Designed to run a single application, such as a virtual web browser.

Whichever VM you select, the VM cannot cross the software boundaries set in place. For example, a virus might infect a computer when executed and spread to other files in the OS. However, a virus executed in a VM will spread through the VM but not affect the underlying actual OS. So this provides a secure platform to run tests, analyze malware, and so on...and creates an isolated system. If there are adverse effects to the VM, those effects (and the VM) can be compartmentalized to stop the spread of those effects. This is all because the virtual machine inhabits a separate area of the hard drive from the actual OS. This enables us to isolate network services and roles that a virtual server might play on the network.

Virtual machines are, for all intents and purposes, emulators. The terms emulation, simulation, and virtualization are often used interchangeably. Emulators can also be web-based; for example, an emulator of a SOHO router’s firmware that you can access online. You might also have heard of much older emulators such as Basilisk, or the DOSBox, or a RAM drive, but nowadays, anything that runs an OS virtually is generally referred to as a virtual machine or virtual appliance.

A virtual appliance is a virtual machine image designed to run on virtualization platforms; it can refer to an entire OS image or an individual application image. Generally, companies such as VMware refer to the images as virtual appliances, and companies such as Microsoft refer to images as virtual machines. One example of a virtual appliance that runs a single app is a virtual browser. VMware developed a virtual browser appliance that protects the underlying OS from malware installations from malicious websites. If the website succeeds in its attempt to install the malware to the virtual browser, the browser can be deleted and either a new one can be created or an older saved version of the virtual browser can be brought online!

Other examples of virtualization include the virtual private network (VPN), which is covered in Chapter 9, “Physical Security and Authentication Models,” and the virtual local area network (VLAN), which is covered in Chapter 5, “Network Design Elements.”


Most virtual machine software is designed specifically to host more than one VM. A byproduct is the intention that all VMs are able to communicate with each other quickly and efficiently. This concept is summed up by the term hypervisor. A hypervisor allows multiple virtual operating systems (guests) to run at the same time on a single computer. It is also known as a virtual machine manager (VMM). The term hypervisor is often used ambiguously. This is due to confusion concerning the two different types of hypervisors:

  • Type 1: Native—The hypervisor runs directly on the host computer’s hardware. Because of this it is also known as “bare metal.” Examples of this include VMware vCenter and vSphere, Citrix XenServer, and Microsoft Hyper-V. Hyper-V can be installed as a standalone product, known as Microsoft Hyper-V Server, or it can be installed as a role within a standard installation of Windows Server 2008 (R2) or higher. Either way, the hypervisor runs independently and accesses hardware directly, making both versions of Windows Server Hyper-V Type 1 hypervisors.
  • Type 2: Hosted—This means that the hypervisor runs within (or “on top of”) the operating system. Guest operating systems run within the hypervisor. Compared to Type 1, guests are one level removed from the hardware and therefore run less efficiently. Examples of this include Microsoft Virtual PC 2007, Windows Virtual PC (for Windows 7), Hyper-V (for Windows 8), VirtualBox, VMware Server, and VMware Workstation.

Generally, Type 1 is a much faster and much more efficient solution than Type 2. It is also more elastic, meaning that environments using Type 1 hypervisors can usually respond to quickly changing business needs by adjusting the supply of resources as necessary. Because of this elasticity and efficiency, Type 1 hypervisors are the kind used by web-hosting companies and by companies that offer cloud computing solutions such as infrastructure as a service (IaaS). It makes sense too. If you have ever run a powerful operating system such as Windows Server 2012/2008 within a Type 2 hypervisor such as Windows Virtual PC, you will have noticed that a ton of resources are being used that are taken from the hosting operating system. It is not nearly as efficient as running the hosted OS within a Type 1 environment. However, keep in mind that the hardware/software requirements for a Type 1 hypervisor are more stringent and more costly. Because of this, some developing and testing environments use Type 2–based virtual software.

Securing Virtual Machines

In general, the security of a virtual machine operating system is the equivalent to that of a physical machine OS. The VM should be updated to the latest service pack. If you have multiple VMs, especially ones that will interact with each other, make sure they are updated in the same manner. This will help to ensure patch compatibility between the VMs. A VM should have the newest AV definitions, perhaps have a personal firewall, have strong passwords, and so on. However, there are several things to watch out for that, if not addressed, could cause all your work compartmentalizing operating systems to go down the drain. This includes considerations for the virtual machine OS as well as the controlling virtual machine software.

First, make sure you are using current and updated virtual machine software. Update to the latest patch for the software you are using (for example, the latest version of Oracle VirtualBox). Configure any applicable security settings or options in the virtual machine software. Once this is done, you can go ahead and create your virtual machines, keeping in mind the concept of standardized imaging mentioned earlier.

Next, keep an eye out for network shares and other connections between the virtual machine and the physical machine, or between two VMs. Normally, malicious software cannot travel between a VM and another VM or a physical machine as long as they are properly separated. But if active network shares are between the two, malware could easily spread from one system to the other. If a network share is needed, map it, use it, and then disconnect it when you are finished. If you need network shares between two VMs, document what they are and which systems (and users) connect to them. Review the shares often to see whether they are still necessary. Be careful with VMs that use a bridged or similar network connection, instead of network address translation (NAT). This method connects directly with other physical systems on the network, and can allow for malware and attacks to traverse the “bridge” so to speak. If a virtual host is attached to a network attached storage (NAS) device or to a storage area network (SAN), it is recommended to segment the storage devices off the LAN either physically or with a secure VLAN. Regardless of where the virtual host is located, secure it with a strong firewall and disallow unprotected file transfer protocols such as FTP and Telnet.

Consider disabling any unnecessary hardware from within the virtual machine such as optical drives, USB ports, and so on. If some type of removable media is necessary, enable the device, make use of it, and then disable it immediately after finishing. Also, devices can be disabled from the virtual machine software itself. The boot priority in the virtual BIOS should also be configured so that the hard drive is booted from first, and not any removable media or network connection (unless necessary in your environment).

Due to the fact that VMs use a lot of physical resources of the computer, a compromised VM can be a threat in the form of a denial-of-service attack. To mitigate this, set a limit on the amount of resources any particular VM can utilize, and periodically monitor the usage of VMs. However, be careful of monitoring VMs. Most virtual software offers the ability to monitor the various VMs from the main host, but this feature can also be exploited. Be sure to limit monitoring, enable it only for authorized users, and disable it whenever not necessary.

Finally, be sure to protect the raw virtual disk file. A disaster on the raw virtual disk can be tantamount to physical disk disaster. Look into setting permissions as to who can access the folder where the VM files are stored. If your virtual machine software supports logging and/or auditing, consider implementing it so that you can see exactly who started and stopped the virtual machine, and when. Otherwise, you can audit the folder where the VM files are located. Finally, consider making a copy of the virtual machine or virtual disk file, also known as a snapshot, encrypting the VM disk file, and digitally signing the VM and validating that signature prior to usage.

One last comment: A VM should be as secure as possible, but in general, because the hosting computer is in a controlling position, it is likely to be more easily exploited, and a compromise to the hosting computer probably means a compromise to any guest operating systems it contains. Therefore, if possible, the host should be even more secure than the VMs it controls. So harden your heart, harden the VM, and make the hosting OS solid as a rock.

Chapter Summary

This chapter focused on the hardening of operating systems and the securing of virtual operating systems. Out-of-the-box operating systems can often be insecure for a variety of reasons and need to be hardened to meet your organization’s policies, Trusted Operating System (TOS) compliance, and government regulations. But in general, they need to be hardened so that they are more difficult to compromise.

The process of hardening an operating system includes: removing unnecessary services and applications; whitelisting and blacklisting applications; using anti-malware applications; configuring personal software-based firewalls; updating to the latest patch or service pack (as well as managing those patches); using group policies, security templates, and baselining; utilizing a secure file system and performing preventive maintenance on hard drives; and in general, keeping a well-maintained computer.

Well, that’s a lot of work, especially for one person. That makes the use of automation very important. Automate your work whenever you can through the use of templates, the imaging of systems, and by using specific workflow methods. These things, in conjunction with well-written policies, can help you (or your team) to get work done faster and more efficiently.

One great way to be more efficient (and possibly more secure) is by using virtualization, the creation of a virtual machine or other emulator that runs in a virtual environment, instead of requiring its own physical computer. It renders dual-booting pretty much unnecessary, and can offer a lot of options when it comes to compartmentalization and portability. The virtual machine runs in a hypervisor—either Type 1, which is also known as bare metal, or Type 2, which is hosted. Type 1 is faster and more efficient, but usually more expensive and requires greater administrative skill. Regardless of the type you use, the hypervisor, and the virtual machines it contains, needs to be secured.

The hosting operating system, if there is one, should be hardened appropriately. The security administrator should update the virtual machine software to the latest version and configure applicable security settings for it. Individual virtual machines should have their virtual BIOS secured, and the virtual machine itself should be hardened the same way a regular, or non-virtual, operating system would be. (That clarification is important, because many organizations today have more virtual servers than non-virtual servers! The term “regular” becomes inaccurate in some scenarios.) Unnecessary hardware should be disabled, and network connections should be carefully planned and monitored. In addition, the administrator should consider setting limits on the resources a virtual machine can consume, monitor the virtual machine (and its files), and protect the virtual machine through file permissions and encryption. And of course, all virtual systems should be tested thoroughly before being placed into production. It’s the implementation of security control testing that will ensure compatibility between VMs and virtual hosting software, reduce the chances of exploitation, and offer greater efficiency and less downtime in the long run.

Chapter 3 builds on Chapter 2. Most of the methods mentioned during Chapter 2 are expected to be implemented in addition to the practices listed in this chapter. By combining them with the software protection techniques we will cover in Chapter 4, “Application Security,” you will end up with quite a secure computer system.

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