Upgrading to a New Microsoft Operating System

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Upgrading to a New
Operating System

by James G. Barr

Docid: 00021035

Publication Date: 1706

Publication Type: TUTORIAL


Windows 10 is Microsoft’s latest operating system for homes and businesses. Microsoft
has pushed its customers relentlessly to migrate to the new
platform, even making the software free for a period of time . Upgrading to a new Microsoft operating system, however, can be
difficult, either because the new OS offers a different user interface, as with
Windows 8, or the install base is large and diverse, a problem peculiar to
enterprise clients. In terms of enterprise adoption, implementing Windows
10 – or a new version of Windows Server – requires careful planning and
significant resources.

Report Contents:

Executive Summary

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Microsoft’s latest operating system for homes and businesses, Windows 10,
has been readily pushed by the vendor so that users would upgrade. 

Faulkner Reports

Microsoft Windows 10 Product

Microsoft Windows Server 2012 R2

Upgrading to a new Microsoft operating system, however, can be difficult,
either because the new OS offers a different user interface, as with Windows 8,
or the install base is large and diverse, a problem peculiar to enterprise

In terms of enterprise adoption, implementing Windows 10 – or a new version
of Windows Server – requires careful planning and significant resources.

Windows 10

Analyst Nathan Eddy contends that enterprise interest in Windows 10 is
informed by several facts:

  • Support for Windows 7 will end in January 2020.
  • Windows 10 is compatible with Windows 7 applications and devices,
    helping preserve an enterprise’s existing IT investment.
  • There is a pent-up demand among enterprise users for tablets – devices
    that are supported under Windows 10.1

Overall, the deployment of Windows 10 should be smoother than other Windows
upgrades given that many enterprises will have recently promoted from Windows XP to
Windows 7 or 8, providing invaluable upgrade experience.

As of 2017, Microsoft has said that more than 400 million devices in 192
countries are running Windows 10. 

Why an Enterprise Should Upgrade

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The decision to upgrade to a new Microsoft operating system depends on
multiple factors. Here are the major factors that favor upgrading.

Business Benefits

As with any enterprise initiative, the process of upgrading to a new
Microsoft operating system must produce real and tangible benefits. In a
software context, this normally means:

  • The availability of new or enhanced features or functions that promise
    to improve enterprise operations, leading to greater productivity and
  • The elimination of operational restrictions, such as removing prohibitions
    against the use
    of certain devices or popular third-party applications or services.
  • Compatibility with new or emerging information systems or services, both
    Microsoft and third-party.
  • Greater performance and scalability (capacity).
  • Greater economy as reflected in a reduced total cost of ownership (TCO).

If an upgrade will advantage an enterprise in one or more areas, the upgrade should probably proceed.

Support Withdrawal

It is generally irresponsible to use a Microsoft operating system – indeed,
any consequential information system or application – after vendor support
is withdrawn. While it may be possible to forego functional fixes, running an outdated operating
system without routine security patches is akin to business suicide.

Here’s a prime example. Windows XP and Vista are no longer supported by
Microsoft. However, when the WannaCry ransomware attacks took place in May 2017
and locked up computers around the globe, Microsoft made an unprecedented move
to issue patches for both XP and Vista because so many millions of computers
were vulnerable to WannaCry as people were still using these outdated operating
systems. This is one example of why it’s always best to use a Windows system
that Microsoft continues to support. Although the vendor did push out updates to
patch against the vicious ransomware, if a system was already infected, those
patches came too late. 

Enhanced Security

Given the frequency and severity of cyber attacks, an enterprise should
strongly consider upgrading to a new Microsoft operating system if the new OS is
judged more secure. According to Microsoft, Windows 10 is "the most secure
Windows ever,"2 offering a potent argument for accelerated deployment
– provided, of course, the deployment can be securely performed.

User Familiarity

The need for extensive – and expensive – user training is often cited as a
reason for delaying a Microsoft operating system upgrade. In the case of Windows 10, however, where Microsoft has strategically
encouraged home user migration, enterprise employers who are also home users
should find it relatively easy to adapt to Windows 10 at work.3

Hardware Modernization

Enterprises normally manage their PC inventories by procuring new computers
and retiring older machines according to a multi-year PC "refresh"
cycle. New PCs often arrive with the latest Microsoft operating system
pre-installed. While it may be possible to order PCs with an older
operating system installed – thus matching the present enterprise standard –
these new units will have to be upgraded eventually to the new OS
– creating additional work for the transition team.

A better tactic is to leave the new machines alone, i.e., with the latest
operating system installed, and upgrade the enterprise’s existing PC pool.

Why an Enterprise Should Not Upgrade

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Here are some factors that favor a cautious approach.

No Substantive Business Benefits

According to analyst Afzal Ballim, "Upgrading an OS is driven by many factors:

  • "Is support running out?
  • "Does the
    new version provide significant improvements for our users?
  • "Does it increase
    security and simplify management?
  • "Does it facilitate mission-critical projects
    that can’t be done otherwise?

"In other words, are there urgent pain spots
that can be solved by the upgrade
? If you cannot answer this question
with a ‘yes’, then where is the
urgency to migrate?"4

Immature or Unproven Software

It is the nature of software that initial or early versions – which receive
limited or no "real world" testing – are often "buggy."
Without an overriding business imperative, it is wise to delay deployment of
a new Microsoft operating system until the OS is, at least, several
generations old and tested.

Insufficient Budget or Staff

Upgrading to a new Microsoft operating system can be expensive. Gartner estimated that converting from Windows XP to Windows 7 cost about
$1,000 per user.5 While that figure might be high,
enterprise officials would be foolish to attempt an upgrade without adequate
budget or staff. To accurately project budget and staffing needs, it would be prudent to
conduct a small-scale pilot program. Such a program would also help
refine upgrade policies, protocols, and procedures – fixing small problems
before they can become big.

Change Resistant Enterprise Culture

Although they may be technology users, many enterprise employees are not technology
enthusiasts and might be resistant to OS upgrade efforts – seeing such
exercises as unrelated to their principal work. If these feelings
represent a prevailing attitude, enterprise officials should defer any
upgrade until:

  • Employees receive "upgrade awareness" training, which should stress new
    OS functionality and security.
  • Upgrade procedures are engineered – or re-engineered – to minimize
    employee participation and inconvenience.

Upgrading to Windows 10

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Upgrading to Windows 10

A free upgrade to Windows 10 ended in July 2016. 

Analyst Michael Niehaus advises that "the simplest path to upgrade PCs that are
currently running Windows 7, Windows 8, or Windows 8.1 to Windows 10 is through
an in-place upgrade." In addition, an enterprise can employ "a Microsoft Deployment Toolkit (MDT) 2013
Update 2 task sequence
to completely automate the process." For
details, consult Niehaus’ Microsoft TechNet article and related posts.6

Updating Windows 10

After upgrading to Windows 10, an enterprise can utilize Windows Update for Business
to keep their Windows 10-based devices current. As analyst Afzal Ballim
explains: "By using Group Policy Objects, Windows Update for Business … enables organizations and administrators to exercise control on how their
Windows 10-based devices are updated, by allowing:

  • "Deployment and validation groups, where administrators
    can specify which devices go first in an update wave, and which devices will
    come later (to ensure any quality bars are met).
  • "Peer-to-peer delivery, which administrators can enable
    to make delivery of updates to branch offices and remote sites with limited
    bandwidth very efficient.
  • "Use with existing tools such as System Center
    Configuration Manager and the
    Enterprise Mobility Suite.

"Windows Update for Business is a free service for
all Windows 10 Pro, Enterprise, and Education editions, and can be used
independent of, or in conjunction with, existing device management solutions
such as Windows Server Update Services (WSUS) and
System Center Configuration Manager."7


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Purge Unused or Obsolete Applications

For many enterprises, upgrading to a new Microsoft operating system offers
an opportunity to perform
some overdue housekeeping. Prior to upgrading, render the information
ecosystem as clean as possible by identifying and purging all unused or
obsolete applications.8

Upgrade Applications to Compatible Levels

Upgrading to a new Microsoft operating system may require the simultaneous
upgrade of critical applications. Check all applications to determine
if they support the new operating system and schedule application upgrades
as needed.9

Establish a New OS Sandbox

Create an environment where employees and business partners can experience –
pre-upgrade – the new Microsoft operating system. If available, a virtual
desktop infrastructure (VDI) would permit employees and others to effortlessly
switch between the present and future OS.

Leverage Microsoft Tools and Advice

Trust the experts. Whenever and wherever possible, invoke Microsoft
tools and program aids to facilitate an operating system upgrade. Importantly,
by relying on vendor materials and methods, an enterprise can more readily and
reliably receive technical support for upgrade-related issues.

Backup Information and Information Systems

As with any major software upgrade – an operating system or otherwise – the
first step is to secure enterprise information and information systems. Backup all applications and data to multiple, protected repositories. Validate the backup process by randomly retrieving and restoring archived data
and compare that data against previously-stored pristine images.

Develop an Incremental Upgrade Plan

Introduce a new Microsoft operating system in phases, usually one or two
departments at a time. In this way, any upgrade-related damage can be contained
and not interfere with overall enterprise operations.

Create a Rapid Reversion Plan

If an upgrade step fails or creates adverse results, it should be possible
to restore the pre-upgrade environment. Even if an upgrade step is
irreversible, an enterprise should still consider how to make any users who are
negatively impacted whole again.

Monitor Information Integrity and Confidentiality

Upgrading to a new Microsoft operating system is inherently disruptive – and
could compromise essential cybersecurity controls. The chief security
officer (CSO) should cooperate with the chief information officer (CIO) to
guarantee that all enterprise information remains protected against loss, theft,
contamination, and misappropriation – especially any employee, business partner,
or client personally identifiable information (PII).

Reduce Upgrade Demands Through Decommissioning

Proactively remove from service any end-of-life PCs or other devices before commencing a
Microsoft operating system upgrade.

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About the Author

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James G. Barr is a leading business continuity analyst and

business writer with more than 30 years’ IT experience. A member of

"Who’s Who in Finance and Industry," Mr. Barr has designed,

developed, and deployed business continuity plans for a number of Fortune

500 firms. He is the author of several books, including How to

Succeed in Business BY Really Trying, a member of Faulkner’s Advisory

Panel, and a senior editor for Faulkner’s Security Management

Practices. Mr. Barr can be reached via e-mail at jgbarr@faulkner.com.

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