Microsoft’s Internet Information Services (IIS) has been around for more than a decade, from its first incarnation... more

Microsoft’s Internet Information Services (IIS) has been around for more than a decade, from its first incarnation in Windows NT 3.51 to the current release of IIS 7.0 on the Windows Server 2008 and Vista platforms. It has evolved from providing basic service as an HTTP server, as well as additional Internet services such as Gopher and WAIS, to a fully configurable application services platform integrated with the operating system.

IIS 7.0 is a dramatic change in the way IIS is configured and managed. Modularity, granularity, and interoperability are the guiding factors across the entire product, from setup to security, management to automation. Integrated heavily into the operating system, IIS 7.0 benefits from the improvements in the Longhorn platform, but IIS has been re-engineered to meet the demands of a true application platform.

This chapter will provide you with an overview of the changes in IIS 7.0 as well as a sampling of some of the new technologies. If you are familiar with IIS 6.0, you will want to skim through this chapter for changes before digging into future chapters for specifics. If you are new to IIS, this chapter will provide an introduction to the features in IIS 7.0 and provide you with a basis for understanding future chapters. And if you’re the kind of reader who just wants to skip to the part that applies to your immediate needs, this chapter can help you figure out in what area those needs will lie.

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The origins of IIS as a service to deliver data via HTTP and Gopher requests determined the architecture of IIS for six... more

The origins of IIS as a service to deliver data via HTTP and Gopher requests determined the architecture of IIS for six generations. Over the years, IIS architecture has evolved from serving simple requests and providing a Common Gateway Interface (CGI), to include interpreted scripting languages for active server pages, or ASP, now referred to as ASP Classic. Newer versions added the ability to include the ASP.NET framework for server-processed programs, as well as brand-new technologies such as AJAX and SilverLight.

Understanding the basic architecture of IIS through previous versions will help you understand the changes in IIS 7.0, as well as help you understand problems in converting applications and sites from previous versions. IIS has often been compared to the Apache open source server, and often derided as not providing the configurability of Apache. Many organizations have chosen Apache as their web platform, often because of misinformation, and in some cases have regretted the decision. While most organizations can work with either web server technology as a base, the choice of web server technology determines many future choices as well, such as the ability to leverage ASP.NET for web applications. In many ways, IIS 7.0 architecture changes void the reasons for choosing Apache as a web platform. IIS 7.0 still supports previous architectures.

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Deploying Windows Server 2008 and IIS 7.0 is a journey, and as in all journeys, you need to know three things:... more

Deploying Windows Server 2008 and IIS 7.0 is a journey, and as in all journeys, you need to know three things: your starting point, your ending point, and the path between. The starting and ending points seem to be the most obvious, but the failure to determine them accurately is why the path in many deployments seems to wander astray. There are also many paths in between—all of which lead to the same point, and all of which have different terrain to be negotiated.

In many deployment scenarios, there are two landscapes to be traversed. The first is technical and is often the easiest. Which piece of hardware or which software setting to use for a specific task is often straightforward. But combining that with the second landscape, which is organizational, and often political, will determine which technical choices can be made. Many times the best technical choice is not the best organizational choice, and it is often hard for administrators to accept, or even see, the organizational hills and valleys that must be traversed.

In this chapter, you will learn what technical choices are available and some options for applying those choices in the organizational landscape. If your organization has no limits to resources like cash and manpower, you will find your choices unlimited. But, if your organization is like most, resources will dictate your range of choices. You may find that your choices are further limited by management choices, developer needs, and other constraints placed by network access or security concerns. Your choices may even be limited by the skill of in-house staff, and, as you read through this chapter, you should honestly assess whether the planning and deployment could be handled by an outside contractor more effectively and efficiently. Even if you will not be responsible for the planning or deployment, this chapter will provide valuable background material that will help you understand why some choices were made.

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There are many ways to install IIS 7.0, from installing it as part of the Windows Server 2008 installation or adding IIS... more

There are many ways to install IIS 7.0, from installing it as part of the Windows Server 2008 installation or adding IIS 7.0 to an existing server to upgrading a Windows Server 2003 and IIS 6.0 installation—not to mention automated or unattended installations.

In this chapter, we assume that you’ve read and understood the deployment planning issues discussed in Chapter 3, “Planning Your Deployment.” You might also want to scan several of the upcoming chapters so that you understand which additional features you might want to install. Chapter 5, “Administration Tools,” as well as Chapter 10, “Configuring Other Services,” may help you.

After reading this chapter, you should be able to:

• Install IIS 7.0 along with Windows Server 2008.

• Install IIS 7.0 into an existing Windows Server 2008 system.

• Upgrade a Windows Server 2003 IIS 6.0 system to Windows Server 2008 and IIS 7.0.

• Install new features in an existing IIS 7.0 installation.

• Install IIS 7.0 from the command line.

• Configure IIS 7.0 for shared hosting recommendations.

• Install IIS 7.0 on Windows Vista.

Future chapters will cover advanced configuration options for IIS 7.0. While this chapter covers adding features to an existing IIS 7.0 installation, you may wish to also look at Chapter 11, "Core Server" and Chapter 18, "Programmatic Configuration and Management" as companions to this chapter.

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In this chapter, we examine the various tools Microsoft has included to administer IIS 7.0. In building IIS 7.0,... more

In this chapter, we examine the various tools Microsoft has included to administer IIS 7.0. In building IIS 7.0, Microsoft had to completely revamp the toolset used to manage IIS. They replaced the old IIS Manager MMC with a completely new IIS Manager application that provides greater functionality for its expanded role. This new admin tool allows developers and administrators to add their own extensions and tweaks to it through its extensibility features. In addition to these major changes to the administrative tools, they added the ability to set web server configuration through files in the web site. They added to the functionality of the web.config file and introduced the applicationHost.config file. Through these files, the developer can completely set up and adjust the web site. They also took the venerable command-line interface (CLI) and added to it with the AppCmd.exe tool, which allows complete control over every aspect of IIS.

In this chapter, you will learn about the IIS Manager, configuration settings, and command-line management using AppCmd.exe.

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The daily challenges that you face as a web server administrator are wide and varied—from managing web-site content... more

The daily challenges that you face as a web server administrator are wide and varied—from managing web-site content or ensuring that the company’s web site is available for the crucial product release to figuring out why the developer’s code that’s just been deployed keeps crashing the web site. To manage such demands successfully and still be able to sleep at night depends on how well the server is administered and your ability to troubleshoot issues effectively and concisely. To develop these skills, you first need to accustom yourself with the core functionality of IIS and the best practices for managing it.

In this chapter, we look at the basic administration tasks required to manage an IIS7.0 web server. We will investigate and look at the best practices of

• An overview of web sites, applications, and virtual directories.

• Creating and modifying a web site.

• Configuring logging.

• Configuring and managing host headers.

• Administering applications.

• Administering virtual directories.

• Configuring compression.

• Configuring MIME settings.

• Basic tasks to hit the ground running.

This chapter will also demonstrate the use of the latest tools for managing IIS 7.0, including IIS Manager, AppCmd.exe, Windows Management Instrumentation (WMI), and managed .NET management classes.

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When you look at most web sites today, you are seeing some type of dynamic content. This dynamic content could be an... more

When you look at most web sites today, you are seeing some type of dynamic content. This dynamic content could be an online auction, webmail, forums, blogs, online games, or any type of nonstatic content that is on a web site. The content is delivered by a web application. Normally, a web application is a three-tiered system, where the browser is the first tier, a dynamic web content technology is the second tier, and a database is the third tier. For our purposes, the dynamic content technology will be referred to as the “web application.” The web application can be based on a variety of technologies, including ASP, ASP.NET, ISAPI, CGI, and FastCGI. IIS 7.0 natively supports these technologies as well as the Windows Communication Foundation (WCF). These technologies all plug into IIS 7.0 via modules that can be added or removed based on the purpose of the server. In this chapter, we shall discuss these technologies and their administration as they relate to IIS 7.0.

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Web sites and applications can be divided into pools of sites that make the most sense to the administrator.... more

Web sites and applications can be divided into pools of sites that make the most sense to the administrator. These pools create complete sandbox isolation between the other application pools on the server, offering strong performance and security benefits.

This chapter covers the various aspects of application pools, from overlapping worker processes during a recycle to the new Integrated Pipeline mode. A background and comparison between IIS 5.0 and IIS 6.0 are covered to set the stage for understanding why application pools are necessary and the advantages that they bring.

Effective management of application pools requires an understanding of

• Application pools, including what a virtual directory and application are in IIS.

• The w3wp.exe worker process.

• The two pipeline modes.

• Multiple methods of creating and managing application pools.

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Many web environments have a need to separate the roles of the system administrators and the web site development and... more

Many web environments have a need to separate the roles of the system administrators and the web site development and management team. Whether there are two people in these roles or hundreds, it is necessary for the server administration team to specify the access level and settings for the developers or deployment team.

In past versions of IIS, the ability to delegate partial administration of a server, web site, or application was very limited. Unless you developed your own tools, it was not possible to configure partial access to the end developer or administrator.

In the area of delegation, IIS 7.0 breaks revolutionary ground in two areas. First, IIS administrators can specify the access the web site administrators should have and provide the IIS Manager tool for them to manage their settings remotely through a user-friendly interface. Second, this same access in IIS Manager also applies to the web.config file. This may seem strange at first because the web.config file used to be for ASP.NET, and it wasn’t possible to manage IIS from any type of control file. The advantages of managing some IIS features from the web site’s web.config file are huge, the most prominent benefit being that web site tool vendors and developers can create web sites and then copy them using a simple tool like XCopy or FTP.

Delegation isn’t just turning on a switch and allowing developers or web site administrators to start work. It requires a lot of planning and understanding of what can and cannot be delegated. In this chapter, we will explore the various levels of delegation, how to set them, and what to watch for.

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In previous chapters you learned to plan, install, configure, and manage the basic IIS 7.0 web server functions.... more

In previous chapters you learned to plan, install, configure, and manage the basic IIS 7.0 web server functions. IIS 7.0 and Windows Server 2008 come with ancillary services that an administrator may want to use, such as an FTP Server and an SMTP Server. There are additional services and third-party tools that may also be helpful to IIS administrators, such as Microsoft’s Log Parser and FrontPage Server Extensions. Although the capabilities of Microsoft’s additional services might be more limited than those of other commercial products, such as comparing the SMTP Server to Microsoft’s Exchange Server, for many functions the included utilities and services provide all the functionality needed and with no additional costs.

Not all IIS servers will benefit from these additional services, thus an administrator should install only the services required. The security exposure of unneeded services should deter administrators from installing them, but these services can bring additional performance overhead, reducing the performance available for the needed functions of the server. Fortunately, all these services can be installed or uninstalled without affecting the IIS 7.0 functions, either during the IIS installation or at any time after IIS has been installed.

If you are familiar with these services in Windows Server 2003 and IIS 6.0, you should find no significant changes in the versions that ship with Windows Server 2008. The FTP Server that ships with Windows Server 2008 has no changes from the FTP Server in its Windows Server 2003 incarnation, although an upgraded version of the FTP Server can be downloaded from Microsoft’s www.iis.net web site. The SMTP service has also seen no change in Windows Server 2008.

There are planning decisions that you need to make before installing and configuring these services, and without the background included in this chapter, the configurations are less than intuitive, especially when configuring FTP. Obviously, each installation environment will dictate how these are configured. For example, intranet use of these services differs from an Internet web hosting service. Plan your installation carefully, and you’ll find these services, even with limitations, quite capable and robust. By the end of this chapter, you should be able to

• Plan an FTP Server installation, including user isolation and directory structure.

• Install and configure the FTP Server, including securing the FTP Server.

• Manage your FTP Server both through the GUI interface and programmatically.

• Install and configure FrontPage Server Extensions for additional publishing capabilities.

• Install and configure an SMTP Server, including securing the SMTP Server.

• Manage your SMTP Server both through the GUI interface and programmatically.

• Install Microsoft’s LogParser tool and perform basic log file analysis.

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As you learned in Chapter 2, IIS 7.0 introduces a brand-new architecture to the IIS family. In previous versions,... more

As you learned in Chapter 2, IIS 7.0 introduces a brand-new architecture to the IIS family. In previous versions, the boundaries between what is part of the web server and what is a plug-in or extension were intuitively apparent. With IIS 7.0 and the new modular structure, the boundaries are less obvious.

In this chapter, we take a closer look at how the underlying IIS web server works, and how it is now possible to define for yourself exactly what functionality is provided by the core server, to maximize performance for your specific applications, and to minimize resource overheads.

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You may be getting the idea by now that the new modular structure of IIS 7.0 is probably the most important new feature... more

You may be getting the idea by now that the new modular structure of IIS 7.0 is probably the most important new feature in the IIS product to date. The previous chapter demonstrated how it is possible to customize the server workload by simply plugging in and unplugging the relevant modules, thereby customizing functionality, reducing resource overheads, and improving performance.

This chapter concentrates on the underlying module system and how independent components can be seamlessly integrated into the core system to enhance or modify the functionality of the basic core system. The following topics are discussed:

• An overview of module extensibility.

• Basic module concepts.

• An example native code module.

• An example managed code module.

• Event tracing from modules.

• IIS configuration extensibility.

• Extending the IIS Administration Tool.

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“We have just installed Application X onto IIS and would like to know what steps we need to take to make IIS secure.”... more

“We have just installed Application X onto IIS and would like to know what steps we need to take to make IIS secure.” This is one of the most common questions that faced in the security arena, and this hasn’t changed from when IIS ran on NT to the present day. The question, however, presupposes that there is some set of discrete steps that can be undertaken to secure IIS, and that there is some finite end point that can be described as “secure.”

Certainly there are a lot of products and organizations that claim to make your server secure or secure your application or secure your organization. As a security implementer (or even just someone with a dilettante interest), to what extent should you place credence in such claims?

This introductory chapter on security covers the following topics:

• The basic principles of network and computer security.

• New or improved technologies in Windows Server 2008 that can enhance your overall network security.

• Configuring IIS 7.0 to enhance the security of your web server.

• Additional items (such as application layer security) that you will need to consider when evaluating overall environmental security.

Beyond this chapter, the next two chapters delve into more specific security areas. Chapter 14 deals with Authentication and Authorization, and Chapter 15 deals with SSL and TLS. These chapters should be read together to get a good understanding of the security technologies and infrastructure that are most important when managing an IIS 7.0 installation.

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Configuring authentication and authorization for IIS and applications running on top of IIS is one of the more complex... more

Configuring authentication and authorization for IIS and applications running on top of IIS is one of the more complex IIS security operations. This is in part because of the number of different authentication options available, partly because both the previous version of IIS (6.0) and IIS 7.0 have offered multiple request processing pipelines, and in part because authentication and authorization are often conflated, even though they are distinct concepts.

Authentication is the process of identifying and proving that identity to a remote service (in this case IIS). Typically, a client or user will provide an identifier (for example, a Windows username) and then will be required to prove that identity. Typically, proof of identity takes the form of something you know (a password), something you have (security token), or something you are (some kind of biometric identification). Two-factor or multifactor authentication systems combine these concepts, requiring multiple pieces of authentication information to prove the end-user’s identity.

Authorization occurs after authentication, and is the process by which a user requests permission to perform an operation (for example, view a file), and the system verifies that operation against an access control list (ACL) maintained for the file or resource. The ACL consists of a set of access control entries (ACEs) that define which users can or cannot perform certain operations. By “operations,” we mean being able to read a file, or modify its contents, or update its properties, or impersonate a user, or perform a backup, or shut down a system, or any other possible thing that can be done. Most operating systems allow the definition of both Allow ACEs and Deny ACEs, and by default if a user is not explicitly listed on an Allow ACE, then he or she is denied access even without a specific Deny ACE being present.

The processes of authentication and authorization are confused because typically they occur at the same time as far as an end-user is concerned. Credentials are supplied, and an immediate answer is provided by the server.

This chapter covers these distinct concepts, enabling you to develop a security strategy for your applications, configure the appropriate settings, and troubleshoot potential issues that arise. In particular, this chapter discusses

• Authentication options available with IIS 7.0.

• How to correctly configure permissions on resources to allow permitted user to access resources, while denying unauthorized users.

• The built-in Windows accounts that IIS 7.0 uses.

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When looking at a strategy to secure your application server infrastructure, it is important to examine several discrete... more

When looking at a strategy to secure your application server infrastructure, it is important to examine several discrete elements:

• Secure the actual server that the application is running on.

• Ensure that only permitted users of the application are able to access the allowed functionality (and that all other users, including malicious attackers, are denied access).

• Ensure that your users know they are connecting to the correct server, and, if required, secure traffic between the client and server.

In Chapters 13 and 14, we discuss many of the security options available with IIS 7.0. This chapter addresses security between the client and the server. Secure Sockets Layer (SSL) and Transport Layer Security (TLS) are industry standard technologies for authenticating machines (or users) and for encrypting traffic between two devices.

Note

SSL is a technology originally developed by Netscape, with v2.0 being the first publicly available release. TLS is an IETF standard that is the successor to SSL, and the latest draft version is TLS v1.2. Currently, the terms “SSL” and “TLS” are used interchangeably in the popular press when discussing secured HTTP traffic. “TLS” is almost always used when discussing securing other protocols (such as FTP or SMTP).

TLS should be considered whenever there is a need to secure the transmission of data from eavesdropping attacks (including credentials) or to ensure message integrity (that data aren’t altered in transit). Additionally, to ensure that the two parties in a conversation (the client and server) are able to trust each other’s server (and optionally client), authentication is built into the TLS handshake process.

Note

TLS is a Layer 4 protocol implementation. This typically means that the use of TLS requires the use of an alternate port. For example, when securing HTTP traffic, TLS-secured traffic operates on port 443, rather than port on 80, which is used for unsecured traffic. For internal applications, IPsec should also be considered. As this operates at Layer 3, the security provided by IPsec is transparent to applications, and no modification is required. Instead, routing devices and firewalls need to allow access for additional IP protocols. This is generally not an issue in internal networks.

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At the time of this writing, prior to the final release of IIS 7.0, half of the top ten busiest web sites in the world... more

At the time of this writing, prior to the final release of IIS 7.0, half of the top ten busiest web sites in the world are running IIS, and within the Fortune 100 sites, more sites are running IIS than any other web platform. This speaks volumes to the scalability and reliability that previous versions of IIS already have in the world of busy web sites.

IIS 7.0 builds on this already solid platform with some welcome additions to web farm support. This chapter covers the new shared configuration infrastructure, which provides centralized IIS configuration files for all servers in a web farm. It also looks at what you need to consider to ensure that there isn’t any single point of failure and that your web farm is able to withstand most any type of hardware or software failure, while still maintaining a fully operational web site.

After looking at the new IIS 7.0 features, this chapter will look at content replication, load-balancing options, and several other considerations that every web farm administrator needs to know to effectively manage a web farm of any size.

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No previous version of IIS has offered nearly the same level of management and programmatic configuration as IIS 7.0.... more

No previous version of IIS has offered nearly the same level of management and programmatic configuration as IIS 7.0. The latest release of IIS has taken large steps in the area of management and has laid a foundation for extensive customization.

The configuration infrastructure is leaps and bounds above IIS 6.0, with the ability to extend the schema, thereby allowing all the programming methods to immediately use the custom extensions. The schema is no longer hard-coded into IIS; instead, it’s fully extensible.

Additionally, with the move away from the metabase and toward the XML configuration structure, mimicking the ASP.NET structure, IIS 7.0 fully supports many of the configuration methods familiar to .NET developers.

If you have made a large investment into custom programs in previous versions of IIS, you will be happy to know that the IIS development team has taken great care to ensure that IIS 7.0 is backward-compatible with existing scripts, allowing you to continue to use your existing code.

This chapter is broken into two main sections: direct configuration and programmatic configuration. Direct configuration refers to understanding the configuration model and many of the underlying principles that can be managed using a simple text editor. After a detailed explanation of the configuration model, we discuss programmatic configuration and methods such as the new managed AHAdmin that lies at the programming API core, the new .NET managed code wrapper, and IIS 7.0 Windows Management Instrumentation (WMI). Additionally, ABO, IIS 6.0 WMI, ADSI, and legacy code support are covered.

We also discuss the configuration file hierarchy, location tags, and how to reference configuration files or location tags specifically. Some areas of IIS tend to mask this complexity, but there are times when it’s important to modify a particular location tag within a particular configuration file. This chapter covers how this is done both from a manual configuration perspective and how to do this programmatically.

The goal of this chapter isn’t to give multitudes of code examples, but rather to give you the tools that you need to understand the configuration files and the programmatic APIs so that you can do far more than what is shown in the examples here.

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After a web site has been built and deployed into a production environment, what then? How do you ensure uptime for your... more

After a web site has been built and deployed into a production environment, what then? How do you ensure uptime for your web application in an environment that is subject to ongoing changes, is exposed to the hailstorm of the Internet, or is subject to more traffic than any other server? How do you keep an IIS 7.0 server operational? The answers to these questions have many forms. After deploying a web server, in some ways, the work has just begun.

Maintaining a web site involves a range of knowledge, skills, and abilities. There are a few different approaches to managing the operations of IIS servers, and all of them have some merit. You will, undoubtedly, want control and predictability from your site on an ongoing basis. Most technicians involved in managing operations will value a constant flow of information and metrics.

In this chapter, we introduce some important topics related to managing production IIS servers. To keep your servers up and the hosted applications functioning properly, you need a way to organize your team differently from when the application was under development. You need a system and organization suited to respond to the daily troubles that plague today’s web server, and to be proactive about ensuring the viability of your investment in the hosted application. We review some of the best sources for putting together a world-class structure for ensuring uptime. We begin by looking more at organizational processes, and then return to a more technical focus later in the chapter. Toward the end of the chapter, we cover the mechanics of two important operation tasks: approving hotfixes and conducting backups.

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After covering operations processes in the previous chapter, it’s time to talk about the technical changes that... more

After covering operations processes in the previous chapter, it’s time to talk about the technical changes that you can make to improve performance and ensure the uptime of your web site. In this chapter, you will learn how to track the status of the IIS services and how to make performance improvements to your web server.

The value to your business of monitoring computer systems is widely accepted by professional organizations. To this end, monitoring tools automate the capture and reporting of performance data. Using a monitoring tool installed on your web server, you can track the history and status of the applications and web-site engines and track the state of operating system services, including IIS. Simply put, monitoring is about collecting data, and optimizing is about using that data to build the best configuration.

Administrators are often unable to act on the data they collect. With performance data, you can establish patterns that will define peak periods of activity, audit capacity, and build detailed upgrade plans, and learn how all the parts of your system interact. The adjustments you make to your web site and servers to improve performance are the subject of the later sections of this chapter. The goal of this chapter is to help you tune your system in the process of maximizing performance across the entire system.

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At first glance, “Diagnostics and Troubleshooting” might not strike you as a very interesting chapter.... more

At first glance, “Diagnostics and Troubleshooting” might not strike you as a very interesting chapter. Let’s put you at ease from the beginning. Whether you are a casual IIS administrator or an IIS professional, you have probably run into many situations in which you wanted to find out why a page was taking a long time to load, why it hung, why it is consuming so much CPU, or why it failed. In this chapter, we will explore together many of the new and existing features and tools that will help you better manage your web platform.

IIS 7.0 brings with it a wealth of new features that many consider to be one of the greatest strengths of this latest version of Microsoft’s web platform. It is easy to get excited about the ability that IIS now gives us to get under the covers and gain access to a wealth of information.

This chapter will start off with many new features that IIS 7.0 offers and then will branch off into various other tools built into the operating system and some additional tools that can be downloaded, to make your troubleshooting skills the envy of your fellow administrators.

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The following modules, from Microsoft’s IIS 7.0 module reference (www.iis.net/articles/view.aspx/IIS7/Managing-IIS7/Configuring-the-IIS7-Ru... more

The following modules, from Microsoft’s IIS 7.0 module reference (www.iis.net/articles/view.aspx/IIS7/Managing-IIS7/Configuring-the-IIS7-Runtime/Configuring-Modules/IIS7-Modules-Overview), ship with Windows Server 2008. Chapter 12 discusses extending IIS 7.0 by adding custom modules.

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This Appendix contains the HTTP and FTP status codes, as listed at http://support.microsoft.com/kb/318380.... more

This Appendix contains the HTTP and FTP status codes, as listed at http://support.microsoft.com/kb/318380.

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This short primer introduces you to the fundamentals of Windows Communication Foundation (WCF), Microsoft’s new,... more

This short primer introduces you to the fundamentals of Windows Communication Foundation (WCF), Microsoft’s new, unified programming model for service-oriented applications. WCF first shipped with Microsoft .NET Framework v3 and is included with Windows Server 2008. It shares several components with IIS 7.0, including the ability to be hosted by IIS 7.0, though not necessarily exposed over HTTP.

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This appendix lists several useful resources and links that can serve as additional reading and reference material for... more

This appendix lists several useful resources and links that can serve as additional reading and reference material for IIS Administrators.

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