Windows Server 2008 R2 Migration Checklist

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q CONDUCTING A SERVER ROLE INVENTORY q ARRANGING SERVER ROLES q MAKING THE MOVE TO VIRTUALIZATION q SELECTING THE RIGHT EDITION CONDUCTING ASERVERROLE INVENTORY

Conducting a Server Role Inventory

if you’re using Windows Server 2003 or Windows Server 2008 as your primary operating system, then it’s time to migrate at least some of those servers to Windows Server 2008 R2. Enhanced features and greatly expanded manage- CONDUCTING A SERVER ROLE INVENTORY ability options make Win2008R2 a solid choice. Most businesses shy away from in-place upgrades, preferring instead to mi-

ARRANGING grate existing servers to brand-new hardware. As you do, there’s a significant SERVER ROLES opportunity to consolidate servers and free up room in your data center. This IT handbook is designed to help you focus on the key considerations during a MAKING THE MOVE TO VIRTUALIZATION migration so that you can make the right business decisions along the way. One important note: Win2008R2 is available only in a 64-bit edition, designed for Intel and AMD x64 architecture processors. A “Windows on Win- SELECTING THE RIGHT EDITION dows,” or WoW64, subsystem permits it to run 32-bit applications, but it cannot run 16-bit applications—including the 16-bit installers that many 32-bit software packages still use. Remember: 32-bit x86 hardware cannot run Win2008R2, so that hardware will either need to be repurposed or left on its current version of Windows. Your first step is to determine what your servers are already running. This can include native Windows components and roles, such as DHCP Server or Active Directory, as well as non-core software, such as SQL Server or Exchange Server, and third-party software.

BETHOROUGH:PROCESSESANDSERVICES Do not conduct an inventory based solely on the Add/Remove Programs Con- trol Panel applet. Instead, have an administrator review the actual processes and services that are installed and running on the server. Account for every active process, either as a core system component—which will be the bulk of them—or an installed application. This is a crucial step. In

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the normal course of business, it’s entirely common for servers to organically adopt additional roles and responsibilities. It’s very common to have a third-party Radius server over here and a fax server over there. As you move to Win2008R2, you’re going to need to ensure that each application is compatible with the new operating system and that you have all the necessary installation media, li- CONDUCTING A SERVER cense keys and so forth to re-install that ROLE INVENTORY After taking an software on new servers. Why wouldn’t software be compatible? inventory of your ARRANGING SERVER ROLES Win2008R2 is the first version of Windows servers’ roles, make a to be available only for 64-bit computers. If notation as to which MAKING THE MOVE a server is already running a 64-bit edition roles are compatible TO VIRTUALIZATION of Windows, then you’re fine. But many with the Server Core servers feature 64-bit hardware and are SELECTING THE installation option. RIGHT EDITION running 32-bit versions of Windows. Although the WoW64 system is robust, it isn’t guaranteed to run every 32-bit application without a problem. Any non- core applications should be thoroughly tested in a lab environment before migration, which is why an initial role inventory is so important. This also applies to Microsoft products: If your 32-bit version of Windows is running a 32-bit version of SQL Server, test that thoroughly using 64-bit Win2008R2 and SQL Server to ensure everything works properly.

INDICATE WHICH ROLES ARE SERVER-CORE COMPATIBLE After taking an inventory of your servers’ roles, make a notation as to which roles are compatible with the Server Core installation option. Win2008R2 ex- pands the number of roles that can be hosted on a Server Core installation. Even if you’ve already thought about this topic, it’s still worth re-examining. Server Core offers a smaller operating system footprint, making it an excellent virtualization candidate, as well as offering generally lower overhead, less

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maintenance and fewer patches than a full installation of Windows. In Win2008R2, the Server Core installation option supports the following roles:

D Active Directory Certificate Services D Active Directory Domain Services (domain controllers) D DHCP Server CONDUCTING A SERVER DNS Server ROLE INVENTORY D D File Services—including Distributed File Services and BranchCache, as well as Services for NFS ARRANGING SERVER ROLES D Hyper-V (Server Core is a good choice for virtualization hosts.) D Print Services

MAKING THE MOVE D Remote Desktop Services TO VIRTUALIZATION D IIS (Web Server), including ASP.NET D BitLocker SELECTING THE RIGHT EDITION D Failover Clustering, except in Standard Edition

Web Edition of Server Core supports a subset of these roles, consistent with Web Edition’s scaled-down roles. It’s worth noting that Server Core lacks the “Windows on Windows” support for running 32-bit applications—that is, Server Core can’t run 32-bit applications. Server Core can run many other third-party applications, provided they don’t have any dependencies that aren’t present on Server Core. For example, most of .NET Framework 3.5.1 exists on Server Core. Most management agents, anti-malware software and other common management and utility software can be installed and run successfully on Server Core.

ADMINISTRATORSNEEDEXPERTISE Server Core does require a more knowledgeable administrator. Because there is no graphical user interface, administrators will need a bit more expertise to ini- tially provision a Server Core installation.

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Much of this can be accomplished through a text-based configuration menu, but inexperienced administrators may be uncomfortable without the familiar GUI. In fact, Server Core can be a good excuse to see which of your IT team members are earning their salaries. If they can’t configure a Server Core computer, then they should probably be occupying more entry-level positions and not higher-end network engineer or network administrator positions. CONDUCTING A SERVER ROLE INVENTORY

NOTE: It is incredibly important to understand that Server Core can run any ARRANGING SERVER ROLES software that doesn’t have dependencies not present on Server Core. It is not limited to its native roles. Server Core can run SQL Server, for example, MAKING THE MOVE permitting an x64-based server to devote more physical memory to SQL TO VIRTUALIZATION Server than to the operating system.

SELECTING THE RIGHT EDITION The trick with most software is simply to understand how to install it without a GUI—using an unattended installation mode in most cases. Be absolutely clear that Server Core is Microsoft’s “way forward” with server operating systems. Expect to see an increased emphasis on “Windows without Windows,” and start ensuring that your staff can support servers that are managed primarily using remote tools and from the command line. Even if you don’t specifically feel a need to move to Server Core today, having one or two servers in-house that use the Server Core will help prepare the way for a larger GUI-free server

presence in the future—which is absolutely coming. I

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Arranging Server Roles

once you’ve worked out what your servers are doing, spend some time having administrators profile the performance of those servers. Here are a few ques- tions to ask: CONDUCTING A SERVER ROLE INVENTORY D Are servers consistently at 60% to 80% capacity?

ARRANGING If so, then it’s likely that they are properly loaded. SERVER ROLES

D Do you have servers that consistently hit more than 80% capacity? MAKING THE MOVE TO VIRTUALIZATION You might consider removing some roles from those servers to help ensure you have capacity to meet peaks in workload.

SELECTING THE RIGHT EDITION D Do you have servers running less than 60% to 70% capacity all the time? Those servers may be candidates to host additional roles, which can improve utilization. You’re paying for electricity, cooling and hardware depreciation either way. You might as well get the most for your money by fully using your servers.

Of course, some server roles work better alongside other roles. For example, few experts recommend that a SQL Server computer do anything besides run SQL Server. However, it’s common for so-called “infrastructure servers” to run numerous network infrastructure-related roles, such as DHCP Server, DNS Server, Active Directory, WINS Server and so forth. You also need to consider any new hardware that will house Win2008R2. More powerful hardware can be used to host a greater number of roles or can be used to handle larger workloads for roles. Again, the goal is to have servers that operate at around 75% capacity most of the time. That provides sufficient pad to handle peaks in workload, while still making the most of your hardware investment.

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Ultimately, the question of whether to add more roles to a server, consolidate roles on fewer servers, remove roles from servers or simply leave everything as is comes down to a number of subjective decisions that will depend entirely on your environment. Consider some of the arguments both for and against consolidation, and see where you feel your organization falls. Your decisions will have an impact on CONDUCTING A SERVER the cost of your migration: Fewer servers mean less ongoing maintenance, ROLE INVENTORY lower hardware costs, lower data center costs and lower Windows licensing costs. Typically, most businesses want to run with as few servers as possible ARRANGING SERVER ROLES while still meeting their business needs.

MAKING THE MOVE If a server has the TO VIRTUALIZATION REASONS TO CONSOLIDATE capacity, then consol- Some of the reasons that you may want to idating related roles SELECTING THE consider adding more roles to a given RIGHT EDITION to a single server can server to help consolidate servers and ease maintenance lower overall costs include the following: and administration.

D If a server is routinely underutilized, then you should definitely consider adding more roles to it. For example, an underutilized domain controller may also be able to be a DHCP Server or DNS Server or might be eligible to run some line-of-business applications.

D If a server is routinely underutilized and is only hosting roles that are also hosted elsewhere—such as DNS Server, Active Directory or WINS Server— then the server might be eligible for decommissioning. That is, if your infrastructure is capable of handling its workload and a particular server is redundant, then it may make sense to eliminate that server.

D If a server has the capacity, then consolidating related roles to a single server can ease maintenance and administration. Roles such as DNS, DHCP, Active

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Directory and WINS are all relatively small workloads, and they are all related to the basic tasks of authentication, network discovery and configuration.

If you are moving REASONS TO SEPARATE to a virtualized CONDUCTING A SERVER Sometimes there are reasons that may pre- ROLE INVENTORY server infrastruc- vent you from consolidating. In those cases, ture, it may make you may want to leave servers with their ex- ARRANGING SERVER ROLES isting pre-migration roles and workloads or sense to separate even move roles to a different or new server roles more than you

MAKING THE MOVE to reduce the workload on a given server. would normally do TO VIRTUALIZATION Here are some of those reasons: on physical servers.

SELECTING THE RIGHT EDITION D If a server is running a business server product—SQL Server, Exchange Server, one of the major System Center fam- ily members and so forth—then it’s often best to dedicate that server to that single purpose.

D If a server is anywhere but on your internal protected network, then remove any roles that are not absolutely necessary to its function. For example, pub- lic Web servers shouldn’t be doing anything but running IIS. Even if your Website requires a database, that database should be on a separate server, preferably separated from the Web servers by a firewall, which permits only communications from the Web servers to reach that database server.

D If you are moving to a virtualized server infrastructure, it may make sense to separate roles more than you would normally do on physical servers. Doing that may increase maintenance tasks like patch management but can make it easier to reposition virtual machines (VMs) as needed to dynamically bal- ance workloads.

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D Certain roles must be redundant to achieve the level of availability you need. For example, having two underutilized domain controllers is desirable because having only one domain controller—however poorly or well it is used —creates a single point of failure in your directory services infrastructure.

CONDUCTING A SERVER ROLE INVENTORY CREATE A MIGRATION TARGET PLAN Once you know what your current servers are running—and you’ve decided what roles to leave on those servers and what roles to move—create a target ARRANGING SERVER ROLES plan for your migration. This plan should include the following information:

MAKING THE MOVE D A list of all existing servers and their roles TO VIRTUALIZATION

D A list of all new servers—both physical and virtual—and the roles they will SELECTING THE RIGHT EDITION host

D A migration plan that indicates which existing servers will migrate to which new servers and which roles will move where

D A list of which Win2008R2 edition each server will run and which ones will use the lower footprint Server Core installation option

Even if you plan to perform in-place upgrades of the Windows operating system, treat a pre-upgraded server as an existing one for planning purposes and treat the upgraded system as a new server. Your plan should indicate which server migrations are actually migrations to new hardware—or into a VM—and

which ones are going to be in-place upgrades. I

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Making the Move to Virtualization

a server migration is an excellent time to begin—or continue—the virtualization of your servers. Win2008R2 runs extremely well as a virtual host either under VMWare’s vSphere products, Microsoft’s Hyper-V hypervisor, or under CONDUCTING A SERVER ROLE INVENTORY Citrix’ Xen virtualization platform. Bear in mind that Win2008R2 is available only in 64-bit editions and should be run only in VMs that are hosted on a

ARRANGING 64-bit host machine. SERVER ROLES Virtualization demands that we revisit long-held assumptions and practices. For ex- Virtualization MAKING THE MOVE ample, many organizations strive to keep TO VIRTUALIZATION demands that we their servers well used at all times—60% to revisit long-held 70% is the target number that many IT teams SELECTING THE assumptions and RIGHT EDITION set. The idea behind this goal is that server hardware is expensive both to acquire and to practices. operate, and a less-busy machine isn’t offering a return on investment. We also tend to use servers to scale up. For example, many organizations would prefer to buy a bigger server for Active Directory services because a single server—no matter how powerful—requires about the same amount of data center space, ongoing maintenance and support. Furthermore, a more powerful server is nearly always less expensive to acquire than two servers, so it makes sense to buy fewer bigger servers. All that changes with virtualization.

LOOKING AT THE HARD COSTS There’s no longer a significant hard cost associated with spinning up a new server—in fact, your only hardware costs are some disk space. Many organizations will use this flexibility to scale out rather than up, particularly for server roles that are inherently distributed and easy to scale out.

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For example, Active Directory domain services or Exchange Server mailbox servers are fairly easy to scale out because they are designed to spread workloads among themselves. DNS Server, WINS Server and numerous other core Windows roles and features can also be scaled out in this fashion to support greater workloads and to provide greater fault-tolerance and redundancy in the event of a failure. CONDUCTING A SERVER The ability of modern hypervisors to overcommit constrained resources such ROLE INVENTORY as physical memory makes it even easier to scale out with less risk. For example, many organizations using VMware vSphere products will overcommit ARRANGING SERVER ROLES memory by as much as 50% on some hosts. That means the total amount The ability of modern MAKING THE MOVE of memory assigned to VMs is actu- TO VIRTUALIZATION ally double the amount of physical hypervisors to overcommit memory available to the host server. constrained resources such SELECTING THE RIGHT EDITION as physical memory makes it even easier to scale out WHENTOMIXROLES with less risk. Provided all of the VMs don’t simul- taneously need all of their assigned memory, this situation can allow higher VM densities per host server while still handling your workload. One technique for designing this kind of overcommit is to deliberately mix roles. For example, the infrastructure server tends to do the most work during the morning logon rush, and then it settles down into a steadier workload through- out the business day. By hosting these VMs with print servers or file servers— which don’t get engaged in their workload until after the morning logon rush is finished—you can better ensure that the physical resources of the host server are highly used at all times. Other considerations that continue to hold true are operating system costs and maintenance overhead. Having one physical machine acting as a domain (Continued on page 13)

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Curbing VM Sprawl

THE UNCONTROLLED PROLIFERATION of virtual machines (VMs), called VM sprawl, can gradually choke the processing power from servers, cause unexpected crashes and prevent the proper failover of VMs from other troubled servers. Upgrades

CONDUCTING A SERVER and patches to underlying virtualization platforms can also have unforeseen con- ROLE INVENTORY sequences for performance and stability. As a result, administrators must be pro- active in preventing VM sprawl and other virtualization problems as they occur. ARRANGING Virtualization lifecycle management is one tactic that can help manage VMs— SERVER ROLES ensuring that only justifiable VMs are created by authorized administrators and that they're used actively and removed to free computing resources for other VMs. MAKING THE MOVE TO VIRTUALIZATION Performance monitoring tools will gauge resource usage for tangible factors like network bandwidth, disk I/O and CPU use. When tracked over time, resource

SELECTING THE load trends can flag potential trouble spots that should be investigated. Almost RIGHT EDITION all performance monitoring tools include email/SNMP traps that will warn administrators when key resources fall outside of established limitations. Identify- ing sudden alarming shifts in resource use can signal early warnings that are essential for quick resolution and minimal disruption to the production environment. Ongoing performance monitoring is also essential for accurate server capacity planning. By watching the trends, administrators can make informed decisions and budget for future upgrades that will accommodate the long-term growth of a business. Server capacity planning is far more preferable—and usually less expensive—than ignoring performance problems until they reach crisis levels. The final element in preventing virtualization problems is thorough, accurate and well maintained documentation. It's easy to forget the vast number of de- tails found in a virtual setting. So keep a record of supporting documentation to ensure that your repairs, restorations, upgrades and improvements will go smoothly. —SEARCHSERVERVIRTUALIZATION.COM

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(Continued from page 11) controller will cost you a certain amount of money to license and to maintain. Having four VMs serving that role will cost you four times as much to license and maintain because they must be individually patched, monitored and so forth. One caveat: With the right edition of Windows acting as the host operating sys- Most successful or- CONDUCTING A SERVER tem, your VM Windows licenses might not ROLE INVENTORY ganizations find that cost you anything at all. But maintaining all of those VMs can be a greater number of ARRANGING SERVER ROLES a cause for concern for some organizations. VMs provides them The potential for VM sprawl is another with more flexibility MAKING THE MOVE worry for businesses that are beginning to and capability but TO VIRTUALIZATION move their servers into a virtualized infra- will not unduly in- structure. SELECTING THE crease maintenance RIGHT EDITION The right answer for most organizations lies somewhere between the two extremes burdens. of fewer bigger physical servers and many smaller virtual servers. Although operating system maintenance continues to consume the same resources per server as it always has, you’re no longer constrained by hardware considerations. Most successful organizations find that a greater number of VMs provides them with more flexibility and capability but will not unduly increase maintenance burdens. That is, if they exercise some

discretion in the creation of new VMs. I

1 3 WINDOWS SERVER 2008 R2 MIGRATION CHECKLIST SELECTING THERIGHT EDITION

Selecting the Right Edition

some organizations believe that they’ll incur lower overhead and less con- fusion if they just use the same edition of Windows on every server. Nothing could be further from the truth. CONDUCTING A SERVER ROLE INVENTORY Each edition of Windows tends to incur almost exactly the same number of patches over time, and each edition is managed in the same way. Choosing the

ARRANGING right edition of Windows for each server can help reduce licensing costs be- SERVER ROLES cause lower end editions are priced lower. Your choice of edition can also help drive the roles assigned to each server. MAKING THE MOVE TO VIRTUALIZATION For example, the infrastructure server tends to use roles that are provided in the Standard Edition of Win2008R2. In many organizations it makes sense to offer only those roles on such servers so that Standard Edition can be used. SELECTING THE RIGHT EDITION Note that the entire discussion on edition selection is primarily price-driven. If your organization has a master licensing agreement with Microsoft, such as an Enterprise Agreement, then you should review your pricing and discuss your specific server needs with your Microsoft representative before making any decisions. Also note that Server Core is not a discrete edition of Windows—it is an installation option available in each edition. There are no price differences between a Server Core installation and the full installation. Server Core merely offers a lower footprint and less ongoing maintenance in the form of fewer patches. Let’s begin with the top-end Datacenter Edition. This supports every server role and capability that Win2008R2 possibly can. It places no limits on any form of connection or capability. It supports up to 2 TB of memory and up to 64 processor sockets. Its biggest distinction is related to the Hyper-V role: When Datacenter Edi- tion is used on a virtualization host, that host may run any number of Win- dows-based VMs without additional licensing costs. In other words, you pay for only the host operating system license, and your guest VMs are covered.

1 4 WINDOWS SERVER 2008 R2 MIGRATION CHECKLIST SELECTING THERIGHT EDITION

Standard Edition includes one such license, and Enterprise Edition includes only four. The retail price for Datacenter Edition is approximately $3,000 per processor socket, so on a four-processor server you would pay $12,000. Again, your pricing may vary depending upon your licensing terms with Microsoft. Client Access Licenses, or CALs, are extra. Imagine that you want to have CONDUCTING A SERVER 12 servers running Standard Edition inside VMs. compares your costs ROLE INVENTORY Table 1 among different editions of Windows as the host operating system. This comparison assumes that the host machine has four processor sockets and that ARRANGING SERVER ROLES each VM will be assigned a single-processor socket.

MAKING THE MOVE TO VIRTUALIZATION Table 1: Cost Comparison of Windows Editions SELECTING THE RIGHT EDITION DATACENTER ENTERPRISE STANDARD EDITION EDITION EDITION

Host operating $12,000 $4,000 $1,030 system licensing

Virtual machine operating $0 $9,672 $13,299 system licensing

Total operating $12,000 $13,672 $14,329 system licensing

As you can see, Datacenter Edition becomes attractive in terms of price with this density of VMs running on a single host. The cutover is about 10 VMs running Standard Edition or as few as three running Enterprise Edition. Aside from the VM licensing, Enterprise Edition is no different than Data- center Edition because it supports the same server roles and capabilities. It is limited to eight processor sockets, although it supports the same 2 TB memory limit as Datacenter Edition.

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Standard Edition is a step down in functionality: D Active Directory Certificate Services (ADCS) support only the installation of Certificate Authorities. No other ADCS features are supported. D Active Directory Federation Services are not included. D File Services support the creation of only one standalone DFS root. D Network Policy and Access Services are limited to 250 RRAS connections, CONDUCTING A SERVER 50 IAS connections and two IAS Server Groups ROLE INVENTORY D Remote Desktop Services are limited to 250 RDS Gateway connections. D Failover clustering is not included. ARRANGING SERVER ROLES D BranchCache Hosted Server is not supported. D Only 32 GB of RAM is supported, with a maximum of four processor sockets.

MAKING THE MOVE TO VIRTUALIZATION Foundation Edition is an entry-level package intended for low-end servers. It has the following differences from Standard Edition: SELECTING THE RIGHT EDITION D Active Directory Lightweight Directory Services are not included. D Active Directory Rights Management Services are not included. D The Application Server role—which includes IIS—is not included. D Fax Server is not included. D Print and Document Services are not included. D DirectAccess Management is not included. D Only 50 RDS Gateway connections are allowed. D Only 8 GB of RAM is supported, with a maximum of one processor socket.

Despite these limitations, Foundation Edition can be suitable for a number of positions within your organization because this role does support all of those capabilities, and those roles will run well within the 8GB of memory that Foun- dation Edition supports. The last major edition is Web Edition, which is positioned as a low-cost alter- native to Linux-based Web servers. This edition is strictly limited in its functionality because it is intended only to support Web server capabilities. Web Edition has the following differences from Foundation Edition:

1 6 WINDOWS SERVER 2008 R2 MIGRATION CHECKLIST SELECTING THERIGHT EDITION

D No Active Directory roles are supported. D IIS is included, but the full Application Server role is not. D DHCP Server is not present. D File Services are not available. D Hyper-V is not available. D Network Policy and Access Services are not available. CONDUCTING A SERVER ROLE INVENTORY D The Background Intelligent File Transfer service is not included. D Remote Desktop Services are not included, except for two administrator- only connections for maintenance. ARRANGING SERVER ROLES D Windows Deployment Services and Windows Server Update Services are not supported. MAKING THE MOVE D Internet printing client is not supported. TO VIRTUALIZATION D Microsoft Message Queuing is not supported. D Quality Windows Audio Video Experience is not included. SELECTING THE RIGHT EDITION D RAS Connection Manager Administrator Kit is not available. D The Remote Desktop Connection client is not installed. D Remote Differential Compression is not supported. D RPC over HTTP Proxy is not included. D Storage SAN Manager for SANS is not included. D The Unix Applications Subsystem is not installed. D The TFTP Client is not supported. D WINS Server is not supported. D Windows Server Migration Tools are not included. D 32GB of RAM and a maximum of four processors are supported.

After considering the servers running in VMs and hosted on Datacenter Edi- tion, you should size the edition of Windows to the server’s intended roles and capabilities. Choose the least expensive edition possible for a server’s intended use, and then decide whether your scenario supports the use of Server Core. Going forward, Server Core should be your default choice, except on specific

servers, where it would be unsuitable. I

1 7 WINDOWS SERVER 2008 R2 MIGRATION CHECKLIST ABOUTTHE AUTHOR

CONDUCTING A SERVER Cathleen Gagne ROLE INVENTORY ABOUTTHEAUTHOR: Editorial Director [email protected] Don Jones has more than 15 ARRANGING Brendan Cournoyer SERVER ROLES years of IT experience and is Senior Site Editor a multiple-year recipient of Mi- [email protected] Christine Casatelli MAKING THE MOVE crosoft’s Most Valuable Profes- TO VIRTUALIZATION Managing Editor sional Award. He is co-founder [email protected]

of Concentrated Technology Marty Moore SELECTING THE RIGHT EDITION Associate Managing Editor LLC and a speaker at technical [email protected] conferences worldwide. Jones Linda Koury has written more than 35 books, Director of Online Design [email protected] including Windows PowerShell: Marc Laplante TFM, Windows Administra- Publisher tor’s Scripting Toolkit and [email protected] Definitive Guide to SQL Server Peter Larkin Associate Publisher Performance Optimization. [email protected]

Contact him through his website TechTarget at www.ConcentratedTech.com. 275 Grove Street, Newton, MA 02466 www.techtarget.com

© 2011 TechTarget Inc. No part of this publication may be transmitted or reproduced in any form or by any means without written permission from the publisher. For permis- sions or reprint information, please contact Renee Cormier, Director of Product Manage- ment, Data Center Media, TechTarget ([email protected]).

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