Upgrading Windows 10: Transformation Success with SysTrack


The benefits of upgrading to Windows 10 are significant and compelling but will only be achieved if performance issues that already exist are properly identified and addressed; just upgrading won't fix them. Even though it is easier to do an upgrade with Windows 10 (covered in section 4; see below), than previous versions of Windows, completing a successful Windows 10 transformation should include a focus on truly improving the end user's experience, while reducing ongoing support costs. Additionally, there should be a focus on increasing productivity, which in turn should help to ultimately improve the bottom line. But these objectives cannot be realized without having actionable intelligence upfront to identify performance issues where they are originating so the upgraded user experience is not impacted by legacy issues that could be carried forward to Windows 10.

Lakeside Software's SysTrack solution addresses the critical need for IT to identify existing performance issues across endpoints and applications prior to upgrading to Windows 10, and new issues that come up after upgrading. Since 1997, Lakeside Software has provided exceptional ongoing assessment, migration planning, and design tools for servers, terminal servers, virtualization, cloud readiness, and endpoint computing success. With a long track record of stability and experience at real‐world customer sites, SysTrack is field proven. Lakeside Software is focused on providing the highest level of sustainably through ongoing assessment, helping you keep end users productive and business-critical software running smoothly before, during, and after a Windows 10 transformation.

SysTrack does this through a patented architecture, coupling a low overhead, lightweight agent with a robust and highly scalable data analysis engine, granting complete visibility to administrators without impacting productivity.

This architecture delivers a complete view of the current systems' performance-related productivity challenges. SysTrack can then send alarm and alert notifications which can also be used to execute automation and remediation tasks leveraging additional management tools. These triggers can be passed to third party systems like Microsoft's Service Manager and System Center. Notifications can also be used to identify and perform manual tasks using other Microsoft cloud-based management tools like Intune that don't support direct orchestration.

The Value of Upgrading to Windows 10

Microsoft's release of Windows 10 in 2015 was a pivotal shift for IT towards significantly reducing deployment efforts and endpoint down time due to security vulnerabilities. Customers had been asking for help from Microsoft in these areas and Microsoft listened.

What Customers Told Microsoft

Figure 1 – What customers want from Windows 10 Source: Microsoft Partner Network

For businesses already running Windows 7 and 8.x devices, the functional enhancements and deployment options available with Windows 10 reduce the amount of IT effort needed to begin and continue upgrades. Windows 10 also introduced a sophisticated feature set to ease customer acclimation and adoption. Here are just some of the primary Windows 10 features:

Windows 10 Innovations for Business

Figure 2 – Windows 10 features Source: Microsoft Partner Network

In addition, end users will benefit from key usability features like the return and upgraded capabilities of the Start button, improvements to the Snap feature, the added ability for multiple, windowed desktops, and a consistent look and feel across desktop and mobile handheld devices. These enhancements are powerful end user adoption and productivity considerations.

Why User Training and Acceptance will be Different this Time

Although the features are robust, users still must want to use them. To help address this, Microsoft made Windows 10 free to users wanting to upgrade their personal devices from Windows 7 and 8.x to Windows 10 within the first year of the release. One of the cooler features of Windows 10 that users really like is the speech interface first introduced on Windows 8 Phones, cleverly named Cortana. Cortana gets to know you and helps you get things done, all while letting you interact naturally and easily. By learning more about you over time, Cortana becomes increasingly useful every day. Cortana will learn your preferences, provide quick access to information, and make recommendations personalized for users while helping them learn Windows 10 faster.

Users took advantage of Microsoft's free upgrade offer, helping to make Windows 10 the fastest adoption of any Windows OS.

Because of this, users will want to take advantage of this offer and will in turn become more familiar with Windows 10 features and usability. As users upgrade their personal devices, businesses will have the added advantage and benefit of not being as challenged with user training or adoption readiness that were costly concerns of the past. In the end these contributing factors lead to additional ease and simplicity, providing motivation to users to also have the same experience at work as they have outside of work. Businesses looking to move to Windows 10 before Windows 8.x reaches its end of support cycle will find these to be motivating factors as drivers for faster adoption rates than the previous windows releases.

Where Windows 10 Delivers Improved Security

"If it isn't broken, don't fix it" is one of the oldest IT adages. In many instances organizations believe that because their systems are up and running, nothing could be wrong. The reality is most systems have some degree of issues that are not being revealed. The challenge is that organizations rarely assess their current environment and therefore are likely to carry many issues into Windows 10. Approaching an upgrade this way poses the risk that users won't accept Windows 10, which will also impact IT's reputation. Often these issues come to light when system compromises occur, which is happening more frequently than ever before and with ever-increasing degrees of sophistication.

Figure 3 – Some critical questions you should be asking yourself Source: Microsoft Partner Network

Even in the face of well publicized data breaches and system outages - and many more that never make it to the news - organizations are still struggling with completing upgrades that would remove or significantly reduce these issues. Losses in productivity, public opinion, critical customer data, and ultimately revenue can greatly impact the long-term reputation of IT for not preventing it all in the first place. Unfortunately reiterating the status quo and minimalist approaches of recent years is no longer tenable in today's business-critical world. The damage done from service disruptions can leave remaining and former IT employees wishing they had done more upfront:

putting much more effort into internally selling the need for a more up-to-date, modern, and effectively monitored IT infrastructure that would avoid the issues and outages in the first place.

To address this, a primary value area and compelling driver for businesses to upgrade now to Windows 10 is the investment Microsoft has made in improving security in the face of newer and more sophisticated types of security threats. Today's security threats are much more interruptive than what's been experienced in the past and businesses need to protect themselves now more than ever before. Figure 4 shows how Windows 10 focuses on Identity, Data, Application, and Device security.

Modern Security Threats Require a New Platform

Figure 4 – Windows 10 security features Source: Microsoft Partner Network

Identity Protection

In Windows 10 you get an easy to use and deploy multi-factor security solution that is more resistant to theft and is phishing proof. It comes with the convenience of a password, but with the security of the best multi-factor solutions. The solution works for consumers and enterprises and is already integrated into Microsoft's onpremises and cloud services.

Data Protection

BitLocker has also been improved. It is highly manageable and will increasingly be provisioned automatically on new devices. To address the needs for data loss prevention (DLP) and data separation Windows 10 now includes an in-box solution. Because of its deep integration into the platform itself the protection is seamless for end users and the protection is the same between mobile and desktop devices.

Threat resistance

Windows 10 includes Device Guard. Device Guard is a combination of hardware and software security features that will lock a device down so that it can only run trusted applications. It also means that even if an attacker manages to get control of the Windows kernel, they will be less able to run malicious executable code after the computer restarts because of how decisions are made about what can run and when.

Device security

Windows 10 leverages hardware based security capabilities to isolate, make the device resistance to tampering, and provide integrity checks that can help reduce malwares' ability to tamper with and hide from the system.

In summary, all of these features will certainly help drive businesses to want to further explore upgrading to Windows 10. But we need to acknowledge the fact that operating system upgrades have not been easy to perform successfully in the past. That alone can slow down upgrade efforts. So, what were the issues and how is Windows 10 helping to address them?

Acknowledging Where Past OS Upgrades were Difficult

As companies evaluate what an upgrade to Windows 10 could mean to their organization, there is an almost defensive reflex to wait and see. As most IT staffers - from the infrastructure architect to the technicians carrying external hard drives doing department by department upgrades - can attest, the upgrade process for many in the past has admittedly been complex and involved a tremendous amount of effort.

Endless meetings, planning, assessing, identifying, remediating, testing, retesting, imaging, reimaging, deploying and post deployment support and training. It's no wonder we hesitate in a moment of fear of the unknown at the thought of yet another OS upgrade. The root of this fear can be summarized in two words: Things Break.

In an effort to avoid that, a huge emphasis and effort is exerted towards making sure that drivers, apps, and webpages work without issues, or with the absolute minimum of issues, so end users can remain productive. The reality is that in many cases things are already broken and we have just become numb to a reduced performance experience while conforming to lower performance standards.

Microsoft has provided enhancements in Windows 10 to make the upgrade process easier, but it still lands on IT to determine and plan which systems are the best candidates for each rollout stage, while also maintaining the existing Windows infrastructure.

Lakeside Software's SysTrack helps IT understand the current environment and its readiness for upgrading systems to Windows 10 while still maintaining older OS devices in the interim of further device remediation before reaching upgrade readiness. SysTrack also helps IT understand which end points, roles, software configurations and dependent systems are ready for a Windows 10 upgrade, while providing a platform for continuous, ongoing assessment as the environment evolves. This is important because it is possible to complete a Windows 10 migration where nothing appears to "break" but the user experience still suffers because applications interact with each other in unknown ways. As an example, perhaps backend resources for applications are moved or migrated as part of the bigger project and this leads to a poor user experience. This is where SysTrack can deliver tremendous value by providing performance benchmarking before and after the upgrade.

Windows 10 Upgrade Options Reduce Past Issues

Figure 5 – Windows 10 Enterprise Deployment Perspective Source: Microsoft Partner Network

Before further exploring where SysTrack reduces overall efforts beyond those available in the Windows 10 deployment options, it will be worthwhile to review precisely where Windows 10 delivers on helping IT reduce the aforementioned deployment efforts.

Microsoft has developed Windows 10 to save IT time and effort by reducing or eliminating the traditional image creation, remediate, test, and deploy process that has made OS upgrades more difficult and costly to manage in the past. Each of the three primary options for Windows 10 deployment - In Place, Off the Shelf, or a traditional reimaging approach - will present their own varying degrees of effort. The addition of the In Place and Off the Shelf options is where IT can significantly reduce upgrade efforts and timelines.

In Place Upgrades

With a broader goal of ending the older OS wipe and reload approach, Microsoft is placing a far greater emphasis on enabling "In Place Upgrades" with Windows 10. Now IT will be able to upgrade a system from the older OS version without reimaging or wiping the device to install a fresh copy of the OS, further removing or reducing the need to deploy software, apply a corporate configuration, apply any patches, and then begin the waiting game to see how quickly the end user can become productive again.

Doing an In Place Upgrade is an ideal approach that will take the existing OS, apply the upgrade within Windows 7 or 8.x, and automatically configure already installed and compatible software for Windows 10 while providing choices for keeping or upgrading drivers. In Place Upgrades in older versions of Windows usually required new hardware or software upgrades to run properly. Since the hardware and software requirements for Windows 10 have not changed from windows 7 and 8.x, this deployment option represents the largest amount of reduced effort for IT to deploy Windows 10.

Off the Shelf Upgrades

Windows 10 offers new runtime configuration tools designed to transform an existing hardware OEM manufacturer supplied device with a preinstalled and configured Windows OS image from their off-the-shelf state into fully configured business devices, without reimaging. By using these types of tools, the amount of time and effort required for configuring the device to make it ready for a person to use can be greatly reduced. Once deployed there is a growing need to still make sure that applications and the new configuration are delivering the highest degree of user productivity.

Traditional Imaging / Fresh Installation Upgrades

Of course there will still be instances where the traditional approach of a fresh OS install or reimage will make sense. There will still be devices that require a fresh OS install as the preferred choice. These systems could have unique configurations or software related issues that will require a fresh install in order to be resolved or remediated. Additionally, there could be performance issues relating to the existing OS configuration that are too great to allow an In Place Upgrade. This approach has been taken in the past in the hopes of reducing post upgrade support efforts but has often been overshadowed by the amount of effort required to create functional images across the enterprise.

Microsoft estimates that a large percentage of the apps already running on Windows 7 and 8.x will work on

Windows 10. Additionally, the hardware requirements are unchanged. Because of this, IT will be challenged postupgrade with devices that initially appeared to be good upgrade candidates even though in reality they are not due to underlying performance issues. A deeper view will be needed beyond hardware and software compatibility to properly measure the quality of the user experience before and after the upgrade.

And upgrading isn't the end of the journey since Microsoft plans on Windows 10 being the last major operating system upgrade. Instead of waiting for a once-every-several-years release, new features and improvements will be regularly rolled out via Windows Update. This makes establishing a comprehensive and actionable view into the ongoing health of end user computing systems after a successful upgrade to Windows 10 a necessity. Especially as the operating system, apps, network and hardware you depend on to conduct business continue to update and evolve.

Measuring and Assessing the Post-Migration User Experience

So how do you determine which Windows 10 upgrade approach makes the most sense? The broad assumption is that Enterprise customers will need to take a look at each approach and may adopt more than one or all options as they streamline their ongoing migration strategy. To address these real challenges for businesses exploring, beginning, refining or executing a Windows 10 transformation plan, IT needs to truly know - through empirical data - which workstyles and workspaces best fit into each of these deployment approaches.

SysTrack helps IT by initially and continuously monitoring the environment so that key areas of performancerelated issues can be readily identified. Groups of systems can be targeted for faster "In Place Upgrade" options, while systems facing performance challenges can be properly identified for additional remediation prior to choosing an ideal upgrade approach. With an understanding of which systems are experiencing performance challenges and what the root cause of those challenges are, systems with low performance issues can be classified for In Place upgrades and properly fitted into the ideal deployment approach, while other systems with un-remediated issues can be classified for an Off the Shelf, or Reimaging installation.

It is also important to capture a performance baseline using SysTrack before and after the migration to measure the ongoing impact of the upgrade to users' overall productivity after the upgrade completes. Through continuous assessment SysTrack provides IT the visibility and focus needed to know when issues from ongoing system changes are beginning to impact the end user experience. SysTrack is completely architected to give IT the tools needed to transform the approach that enterprises take to deploy, manage, secure, improve, and report on the end user experience.

Combined with SysTrack, IT can now more effectively leverage existing investments in IT management solutions to execute an upgrade plan that greatly reduces effort while focusing on the most productive upgrade deployment path(s) for the business.

SysTrack Makes your Windows 10 Transformation a Success

SysTrack is a platform upon which a series of tools have been built that includes visualizers, dashboards, management kits, automation frameworks, and custom reports. By following a fundamental methodology of Assessment, Implementation, and Management using SysTrack, areas of improvement are readily identified while issues can be resolved quicker when they come up. After the upgrade to Windows 10 has been completed there is still a need to evaluate the endpoints on an on-going basis.

Analysis Phase: Use SysTrack to establish a performance baseline and identify applications and use cases which may already suffer from poor user experience. That data can then be used to determine the best upgrade path and remediate application issues. For customers seeking a virtual desktop solution for Windows 10, SysTrack has an image planner to help with image design and application rationalization.

Implementation Phase: Integration with the Citrix ® AppDNA application compatibility tools allows project managers to see which applications are considered compatible. They can keep using health scoring to determine the impact on the user experience in the first pilot user groups.

Management Phase/Post implementation: SysTrack gives visibility, security, and control over physical and virtual desktops, as well as remote and local applications all designed around a methodology of continuous assessment. By continuing to use SysTrack for operational monitoring, root cause analysis, trending, reporting, and ongoing business intelligence, customers will achieve higher levels of user satisfaction and productivity.

Figure 6 - SysTrack Resolve shows system usage, active applications, and websites

As enterprises are complex and continually changing, there is a pressing need to discover the most critical aspects of end user activity and plan versatile, streamlined methods to execute a Windows 10 migration strategy. Traditionally the largest burden with this kind of analysis has not just been a simple inventory, but rather identifying distinct workflows tied to actual application and web usage to properly plan the underlying architecture for an operating system upgrade.

Figure 7 - SysTrack Resolve shows individual endpoint health scoring details

For the Service Desk, SysTrack enables easy but granular desktop analysis by allowing a drill-down into a single user or system. If focused on the user, SysTrack presents a list of systems where that user was active. Drilling down deeper into the individual system will give deeper details into the user's experience on that system. If focused on a system, SysTrack presents data for all users on that system. Session history within SysTrack can identify precisely when a user logged in and out, which system(s) they were logged in to, and not only what applications they ran but more importantly SysTrack can measure the time that applications were actively focused on and being used.

Figure 8 - SysTrack Visualizer showing Software Packages by number of recent users

SysTrack also provides integration to Citrix AppDNA and can work alongside other leaders in the deep application remediation space, providing application usage and performance data to these solutions for identification of applications that could benefit from upgrading or patching to achieve a better experience on Windows 10. Citrix®

(AppDNA), Dell® (Changebase) and Flexera Software® are focused on assisting customers with detailed application remediation. Flexera Software also includes options for managing software licenses and repackaging applications for deployment. Existing Integration between SysTrack and Citrix's AppDNA helps to shorten migrations by combining assessment data, migration design, and swifter application remediation.

Figure 9 - Resolve Tool showing an application with a high latency backend network connection

SysTrack also maps the systems and application dependencies, and auto-detects latencies between systems. Benefits include access to application dependencies not readily apparent that are impacting application performance, even though the user may not be able to measure the losses in performance immediately. With this data, reductions in the likelihood of making server and endpoint changes that negatively impact system and application performance can also be realized.

Figure 10 – SysTrack Image Planner generates blueprints of system images

SysTrack Transform and Image Planner are additional tools that help to provide a blueprint for implementation of golden images and VDI desktop pools based on real user behavior and actual application demand to minimize the need for multiple OS images. Together, along with additional built in tools, SysTrack delivers ever-increasing value, while being recognized as the End User Computing Success Platform.


SysTrack is transparent to users, easy for administrators, and indispensable to CIOs. Deploying SysTrack to analyze your existing infrastructure is the fastest, most comprehensive and non-intrusive approach towards understanding and identifying performance bottlenecks in existing systems that impact the user experience. SysTrack identifies which systems are impacted so that you can better identify issues that you do not want to carry forward during your upgrade to Windows 10.

SysTrack provides the data to answer key user experience and system performance questions such as: Is the user receiving a "good" computing experience? What applications are the users utilizing? Should this user be moved to Windows 10 now? If not, what is the critical path for change to be ready for upgrading; new hardware, software upgrades, unique configuration, bring your own device candidate? What websites are my users using? What is the health of the users' desktop experience? What is the daily usage pattern of this user? What applications can move due to higher performance scoring, versus which applications are impacting performance? How productive are my users versus how productive do they need to be? What systems has the user logged into?

These are just some of the key questions Lakeside Software customers can answer as Windows 10 migration planning is explored. With SysTrack, IT can perform accurate capacity planning forecasts based on real data while developing right-sized roll-out plans for Windows 10 and newly upgraded applications and delivering continuous health assessments. With SysTrack:

  • Collect and visualize application and network utilization data on desktops & laptops, and other mobile devices
  • Understand the factors that determine end user experience and how they interrelate
  • Discover and diagnose poorly performing applications/systems
  • Perform historical analysis to understand how a problem developed
  • Quantify resource utilization for accurate capacity planning
  • Monitor application performance and create application audit trails
  • Set up proactive monitoring and alerts with real-time health checks
  • Reduce unused hardware & software
  • Plan a strategy over time based on empirical data

Next Steps

Step 1

Use Lakeside's SysTrack as your IT analytics tool to assess the existing end user environment to analyze areas of waste, user experience health issues, infrastructure sprawl, archaic and redundant applications, anomalies in the environment, opportunities to improve end user productivity and measuring the quality of IT services delivered. We generally recommend SysTrack is deployed 2-3 weeks prior to any transformation.

Step 2

Once an endpoint or virtual desktop and required applications are upgraded to Windows 10 and configured, use SysTrack to continually monitor the user and system health to validate, measure, and identify any new performance areas that could impact the business with productivity losses. Is it a configuration change? A threat? On the endpoint? In the datacenter?

SysTrack can enable you and empower your organization in providing the evidence needed to help drive your success and peace of mind through an updated and modern infrastructure.