Windows 10 upgrade

Windows 10 Upgrade

Microsoft ended general support for Windows 7 in 2015, and Windows 8.1 in 2018, asking everyone to move to Windows 10. Microsoft does have extended support contracts – mostly for businesses which are slow to upgrade (Windows 7: ends January 2020, Windows 8.1: ends January 2023).

However, these dates are coming fast – when you consider all the steps necessary to evaluate, build and roll-out a new operating system.


Why do I need to move to Windows 10 though? My current operating system works perfectly fine!

An example of why having is important, is a while ago, a set of SSL certificates (used when communicating with HTTPS/web pages) were found to be compromised. This would allow hackers to pretend to be a legitimate and secure web site, such as your bank’s web site. Can you imagine hackers having access to your bank? Your online medical records when you book a doctor’s appointment?
Windows 7 and 8 received patches to block these SSL certificates, but Windows XP did not as it was no longer supported by Microsoft. After much uproar, Microsoft did release a patch, but stated it would not do it again, telling users to upgrade to Windows 7 or 8.1.
By that time, Windows 7 Service Pack 1 had been released and many people had already migrated their home computers. Any new hardware which was purchased at the time came with Windows 8.1. Hardware purchased today will come with Windows 10.


The new Windows 10 lifecycle

Each release of Windows 10 is now given a “build number”, and its support period comes from that. For example, Windows 10 build 1809 was released November 2018, and is supported until May 2020 (Enterprise/Education versions until May 2021).

This puts an increasing demand not only on end-users, but on all businesses (small, medium and large) to have not only your Windows roll-out automated in some fashion, but to have the OS upgrade process automated in some fashion too. Your office applications, legacy and modern hardware support, as well as your proprietary applications all need to be able to endure this new upgrade schedule.

The first release of Windows 10 was July 2015, and there have been seven build releases since then (the latest, May 2019, saw build 1903 released). Microsoft current states each build will have support for 18 months.


Preparing for your Windows 10 Upgrade

Joho can help you with the preparations you need, but here we list everything you need to do if you want to perform it yourself.

What you need to do before:

Perform a visual site-survey to verify existing hardware

Joho can help you with an automated scan, followed up with a visual check.

It’s essential to understand what computers you have on your network, including laptops or desktops with your off-site/remote colleagues. Running your automated scan is good, but you need to verify the hardware is where you think it is. You should also verify hardware serial numbers to confirm if the hardware is under a support contract or its support contract has expired – possibly making the hardware unsupported for Windows 10.

Determine which types of computers will be upgraded/replaced

Joho can help you with your analysis and prepare recommendations.

Adding an SSD into an older computer can double or triple the responsiveness of the computer. This is a beneficial step to perform prior to the upgrade of Windows 10. However, if the hardware is not supported under Windows 10, you should not upgrade it. Check with your hardware supplier if the hardware can run Windows 10 – the driver model has changed compared to Windows 7 and Windows 8 – those drivers will not function under a Windows 10 OS.

Build a test system

Joho can have an engineer sit with your team and help you build your test system

Your standard application set should work fine with Windows 10 if they were well written, but given the changes in Windows 10, it is possible there are in-house applications that will not fully work with Windows 10. It is important to have a test installation run the software and verify all functionality is correct. Your vendor might have already tested your application and have a new version ready for you.

Other applications, such as the Microsoft Office suite have newer versions (2016, 2019 or 365 Cloud) which can be tested with a set of internal documents. Microsoft Excel 2019 supports the same VBA macro set as earlier versions, so your spreadsheets should test fine.


After the test system is built, it is important to get the various department heads in your organization come and test the Windows 10 machine to see that it’s very similar to their current desktop/laptop. An operating system upgrade is a big effort, the potential business interruption and down-time, which could happen if there are issues, will make management interested in seeing the test build and asking questions important from their point of view.

The Roll-out method and Gold Master Image

Joho can help you build and test your Gold Master image and your preferred roll-out method

When you have finished testing the Windows 10 system, it is time to build the Gold Master. How you build this depends on your roll-out method. If you have a small business, it is likely you will only have one or two machines to upgrade each night because of user support questions the following day. Mid-sized business will likely upgrade 20 machines a day and large businesses entire departments over a weekend.

It’s likely as a small business you don’t have an Active Directory (AD) Domain Controller (DC) (or perhaps you do for centralized user and workstation security?), so deployment of Windows 10 will probably be a manual installation on each desktop/laptop, perhaps with common settings created from the Desktop Provisioning Wizard (Wi-Fi network, local administrator account and password, standard application installations, etc).

For mid- and large-size business, your DC should be functional, and probably you have Windows Server 2012 R2 or newer. Microsoft lists the following scenarios, using either Microsoft Deployment Toolkit (MDT) or System Center Configuration Manager (SCCM) to deploy Windows 10.

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