Azure e-book series

Preparing for
Windows Server
2008 end of
support
Options and tools for planning
your next move
Who should
read this
e-book?

This e-book is intended for business decision

makers, technical decision makers, solution
architects, technology architects, IT leaders,
and IT managers. In this book, we’ll walk you
through your options for a cloud migration, key
considerations, and resources to help you along
the way.

© 2018 Microsoft Corporation. All rights reserved. This document is provided “as is.” Information and views expressed in this document, including
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01 / 02 / 03 /
Introduction 4 Why upgrade? 5 Three steps to planning 6
your migration

04 / 05 /
Why choose Azure? 10 Key understandings 12
 Chapter 01
July Introduction
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2018 adipiscing elit

01
Introduction
As Windows Server 2008 and 2008 R2 Migrate to Azure, get free Extended
reach end of support on January 14, 2020, Security Update. End of support is an
it’s the ideal time to look for opportunities ideal time to transform your IT estate with
to move your digital assets to the cloud. the cloud. But we know that it can be hard
to upgrade everything before the end-of-
Whether you have one legacy server and
support timeline. To address this need, we
application or hundreds of servers, a digital
are pleased to announce that Extended
transformation to the cloud can help you
Security Updates will be available for free
ensure compliance, enhance security, and
in Azure for 2008 and 2008 R2 versions of
take advantage of a decade of innovation in
Windows Server (and SQL Server) to help
Windows Server.
secure your workloads for three more years
after the end-of-support deadline. You
Options for moving can rehost these workloads to Azure with
to the cloud no application code changes. This gives
Microsoft provides various benefits for you more time to plan your future path,
Windows Server 2008 support extension, including upgrading to a newer version
upgrade, and licensing. such as Windows Server 2016 and utilizing
the rich set of platform services available
Upgrade Windows Server on Azure in Azure.
at no additional cost. When migrating
Windows Server 2008 to Microsoft Azure, Use existing Windows Server licenses.
you can upgrade later to a newer edition of Azure Hybrid Benefit lets you use existing
Windows Server VM at no extra cost. Windows Server licenses to save on VMs in
the cloud. See how much you can save.
 Chapter 02 Why upgrade? 5

02
Why
upgrade?

There are compelling reasons to upgrade and compliance risks. The 2008 family of
from Windows Server 2008, as technology products was great for its time, but we
has evolved considerably since the release highly recommend upgrading to the most
of that edition. current versions for better performance,
efficiency, and regular security updates.
The current edition of Windows Server is a
cloud-ready operating system that supports
workloads and introduces new technologies
for an easy transition to the cloud. You Take the opportunity
can move to a newer edition of Windows to transform
Server on-premises and incorporate hybrid
Cloud computing offers a fundamental
coexistence, enabling a mix of upgraded
shift in the way technology resources
on-premises applications and rehosted
are procured, used, and managed. In the
workloads. Eventually, you can rearchitect,
older model, organizations had to take
rebuild, or build new applications that are
responsibility for all levels of technology.
native to the cloud.
With cloud computing, the responsibility is
End of support means the end of regular distributed between cloud providers and
security updates. With cyberattacks the organizations that use their solutions.
becoming more sophisticated and frequent, This shift in responsibility is one of the
running apps and data on unsupported essential concepts in developing your plan
versions can create significant security for migration to the cloud.
 Chapter 03 Three steps to planning your migration 6

03
Three steps to planning
your migration

Step one: Assess Detailed assessment reports can help you

better manage your migration portfolio.
When creating a cloud adoption plan, it’s
Microsoft Assessment
critical to discover existing infrastructure
and Planning Toolkit
and workloads that need to move. You’ll
have to identify the workloads that are on The Microsoft Assessment and Planning
Windows Server 2008 or 2008 R2, assess (MAP) Toolkit is an agentless, automated,
existing infrastructure to determine exact multi-product planning and assessment
workloads to migrate, create a migration tool that enables faster and easier desktop,
portfolio based on business priorities, server, and cloud migrations. MAP provides
account for migration risks, and estimate detailed readiness assessment reports
how much it will cost to run workloads and executive proposals with extensive
on Azure. hardware and software data, as well as
recommendations to help accelerate your
Tools and guidance for IT infrastructure planning process.
infrastructure assessment Azure Migrate
Microsoft provides tools and guides to Azure Migrate is a service within Azure
help you inventory existing workloads, that helps you assess on-premises and
accurately assess them, and identify virtual machines for migration readiness.
the level of compatibility for migration. It determines the migration suitability
 Chapter 03 Three steps to planning your migration 7

of the machines and provides sizing Azure Migrate analyzes the performance
recommendations for Azure VMs based on history of the machine to identify the VM
performance history. size and disk type for Azure.

Identifying compatibility with the cloud Assessing app migration risk

Before migrating, run assessments to Once a migration portfolio is created, it’s
determine whether on-premises workloads important to determine migration risks
are suitable for migration. Azure Migrate and assess and define scores based on
assesses on-premises machines for the complexity of apps and impact of
suitability and categorizes them as Ready migration. Migration risk depends on
for Azure, Conditional ready for Azure, Not two factors:
ready for Azure, or Readiness unknown.
Business impact. Assess how important
the workload is to your business operations.
Defining a migration portfolio
To determine which applications you Complexity. Evaluate how complex the
should move, it’s important to create a well- application is and how well your team
attributed catalog of applications managed understands it.
by IT, weigh the relative importance of each A critical workload will score a higher risk
attribute, and build a prioritized list even if it’s simple, whereas a more complex
of applications. but less critical workload might end up
Inventory/migration portfolio with a lower risk score—and so might be a
better candidate for early migration.
You might include the following in a
workload migration portfolio:
Calculating the cost of cloud adoption
ffCustom line-of-business applications
To calculate total cost of ownership (TCO)
ffMicrosoft server applications
and estimate monthly budgets, you can use
ffApps from other software vendors free Microsoft tools, including:
ffServer roles
Azure TCO Calculator
The Azure Total Cost of Ownership (TCO)
Right-sizing Azure resources Calculator is used to quickly compare the
After a machine is marked as ready, Azure TCO of an on-premises infrastructure with a
Migrate sizes the VM and its disks for Azure. comparable Azure deployment so you can
If performance-based sizing is specified, estimate the savings.
 Chapter 03 Three steps to planning your migration 8

Azure Hybrid Benefit Savings Calculator Upgrade

You can significantly reduce costs—up to It’s time to upgrade if you have some
72 percent as compared to pay-as-you- workloads running on Windows Server
go prices—with a one- or three-year term 2008 or 2008 R2 that you want to keep
on Windows. Save by using on-premises on-premises. You’ll benefit from the latest
Windows Server licenses with Software edition of Windows Server, which helps you
Assurance. For each license, Microsoft will get cloud- and DevOps-ready while you
cover costs of the OS (on up to two VMs), support current workloads. Windows Server
while you pay only for base compute costs. gives you two upgrade options to choose
The Azure Hybrid Benefit Savings Calculator from. Your choice will depend on your
can help you estimate how much you’ll save. existing operating system and your approach:

A clean installation allows you to review

Building readiness and training plans
system requirements for Windows Server
While preparing for cloud adoption, you’ll
2016, back up your data, and plan to later
need to build readiness and training plans.
reinstall your applications and server roles.
A variety of options are offered to help
learners at all levels develop their skills. Server role migration is the
These options include Microsoft Virtual recommended upgrade process. First you’ll
Academy, IT Pro Cloud Essentials, and IT Pro move from your existing operating system
Career Center. to the latest version of Windows Server on
new hardware or VMs, and then you’ll move
Step two: Migrate roles and services to the new computers.

Microsoft migration tools and guidance

Migration
can help your IT teams understand various
You can migrate Windows Server 2008 and
approaches for migrating Windows Server
2008 R2 VMs by rehosting (also known as
2008 and 2008 R2 workloads. From there,
“lift and shift”) to minimize the amount of
you just decide the right mix of approaches
change required to move an application
for your workloads.
or workload. Rehosting involves moving
applications or services to Azure-based
VMs. This approach doesn’t require code
 Chapter 03 Three steps to planning your migration 9

changes and allows quick migration. You

Step three: Optimize
can rehost by using Azure Virtual Machines
or Windows Server containers. Optimizing workloads on Azure is a process
of streamlining your cloud resources
Modernization continuously to enhance security, improve
performance, and maximize return on
Based on your migration portfolio, you can
investment (ROI).
modernize workloads on-premises and
move them to Azure, or you can onboard Cost Management. Azure Cost
workloads to Azure with lift and shift and Management allows management of cloud
plan for their modernization. spending with transparency and accuracy.
Learn more about the tools for monitoring
Refactor applications
cloud costs and budgets.
Refactor by modernizing application
deployment architectures. This retains Security and governance. Rely on
existing application code and logic. the Azure Security Center for unified
Check out Windows Containers or Azure security management and advanced
Kubernetes Service (AKS) for refactoring. threat protection across your hybrid cloud
workloads. Detect threats quickly, take
Rearchitect applications
responsive action, and reduce your exposure
Rearchitecting is modifying an existing by enabling adaptive threat protection.
application’s code base to optimize it for
scalability and the cloud platform. Cloud health monitoring. Monitor your
Learn how this approach lets you Azure apps with tools like Azure Monitor
develop independently. or Log Analytics to get visibility into their
performance, infrastructure, and data.
Rebuild applications
Data protection. Avoid costly business
When rebuilding greenfield applications,
disruptions, meet compliance goals, and
consider using cloud-native technologies
protect your data against ransomware
to take advantage of the high productivity
and human error by backing up your apps
of platform as a service (PaaS) and rapid
in Azure. Learn about the benefits
application development.
of Azure Backup.
 Chapter 04 Why choose Azure? 10

04
Why
choose
Azure?

Cloud adoption is on the rise, with 87 percent it’s important to understand the benefits
of organizations planning to merge their of Azure as a comprehensive cloud
on-premises datacenters with a hybrid platform. Azure is a consistent hybrid
cloud or the public cloud, according to a cloud with an unmatched number of
recent IDC survey.1 Likewise, worldwide regions. It enables unparalleled developer
spending on public cloud services and productivity, and offers comprehensive
infrastructure is forecast to reach 160 compliance coverage—including meeting
billion USD in 2018, an increase of 23.2 the requirements of the General Data
percent over 2017.2 In this environment, Protection Regulation (GDPR).

1
Worldwide Semiannual Public Cloud Services Spending Guide. IDC

2
Worldwide Public Cloud Services Spending Forecast to Reach $160 Billion
This Year. IDC
 Chapter 04 Why choose Azure? 11

Azure—the cloud for Global scalability. Moving to a cloud like

Azure enables global distribution, with
Windows Server defined service-level agreements (SLAs)
You can migrate to Azure with confidence. on performance. The more locations you
Azure runs on Windows Server, so it’s easy need to work with, the greater the potential
to move workloads to the Azure cloud benefit from the global reach and high
platform. You can take advantage of your availability features of Azure.
existing investments in Windows Server
Improved security and compliance.
licenses and get support in one place. Azure
Azure continuously works to protect data
connects data and apps on-premises to the
and its integrity with a robust suite of
cloud and lets your organization determine
security monitoring tools and controls.
which computing resources stay in-house
Powerful network security, access and
and which move to the cloud.
authorization controls, and auditing
features add oversight and peace of mind.
The business value of Moving workloads to Azure can help you
moving to Azure focus on managing the application actions
By migrating Windows Server workloads and policies required to remain compliant.
to Azure, you can minimize the time and Reduced maintenance overhead. You can
resources spent managing infrastructure reduce IT overhead and maintenance costs
and focus instead on innovation and by moving line-of-business applications
business growth. built on older editions of Windows Server
Flexibility to deploy or develop. Azure to the latest edition—significantly reducing
enables you to quickly migrate, create, and the work required to operate, secure, and
configure Windows Server VMs. You can maintain these applications.
easily lift and shift on-premises Windows
Server 2008 VMs to Azure. Once on Azure,
legacy applications can be modernized
for the cloud. You can move applications
into containers, rearchitect them using
microservices architectures, or rewrite them
using Azure PaaS services.
 Chapter 05 Key understandings 12

05
Key understandings

ffCloud adoption can help ff Azure can help you manage ffBy using Azure Hybrid
your organization meet its the Windows Server 2008 Benefit, you can save up
business and technology end-of-support transition. For to 80 percent on Azure
requirements. no extra charge, you get three virtual machines.
more years of security updates
for Windows Server 2008
and 2008 R2.

Azure Migration Guide for Windows Server

Windows Server 2008 end-of-support resource center