With Windows 10 reaching the General Availability (GA) milestone on July 29, 2015, many IT professionals are looking forward to an upgrade from the aging Windows 7, and the awkwardly designed Windows 8 and 8.1. However, considering the extremely quick pace of development from the release of the Insider Preview to GA, there are some considerations to keep in mind when making the migration.

1: Don’t deploy on Day 1

From a public-facing standpoint, Windows 10 follows a vastly different development process than previous versions. The Service Pack model has been done away with in favor of more frequent incremental feature updates. While the current build (10166) and the three builds prior to that have largely been dedicated to bug fixes and ensuring everything is functioning prior to GA, patches for bug fixes and compatibility issues will inevitably emanate from Microsoft after the initial release.

Note: Enterprise users need to check their Software Assurance privileges for licensing rights. Home and Professional users can freely upgrade to Windows 10 through July 29, 2016.

Update on 7/15/15 with details from Microsoft: I reached out to Microsoft’s Media Relations for more details regarding the release of Windows 10 Enterprise and future Windows Server products. Here’s what I was told:

We encourage businesses to start testing Windows 10 features and functionality now through Windows 10 Enterprise Insider Preview. We’ll continue to add new features – and innovations within features – over time. And starting Aug 1 active Software Assurance customers in Volume Licensing can upgrade to Windows 10 Enterprise as part of their existing Software Assurance benefits.

Windows Server 2016 Technical Preview #2 was released on 5/4. Expect additional Technical Previews through the rest of 2015. Windows Server 2016 will be generally available in 2016. We don’t have additional details to share at this time.

2: Learn about Windows 10’s new update branches

The way in which updates are provisioned in Windows 10 is a reflection of the rapid releases of Chrome and Firefox, and — to an extent — the release schedules of Linux distributions. Windows now has two versions of Windows Update: one standard version and Windows Update for Business, which is included for Pro and Enterprise SKUs.

Windows now also has four (or five, depending on your perspective) update branches.

Windows Insider Preview Branch (WIPB)

As it is presently, this contains both the fast ring and the slow ring. The fast ring serves as the trunk, whereas the slow ring is slightly more polished.

Although perhaps it’s a bit heavy-handed to draw a comparison to a well-established branching model in Linux, the WIPB is somewhat analogous to sid or unstable in Debian.

Current Branch (CB)

The first entry for the CB will be the GA release scheduled for July 29, 2015. Releases on this branch are considered sufficiently stable for consumer releases, while still introducing new features at a pace sufficiently responsive to the market.

Continuing with the Debian comparison, CB is analogous to debian-testing, which offers new packages and features at a sufficiently rapid pace. (Of note, Debian’s reputation for stability in the testing branch is strong enough that the bi-annual releases of Ubuntu are derived from this branch.)

Current Branch for Business (CBB)

This branch is intended to contain snapshots of the CB, but with different handling of feature upgrades. The feature upgrades will be introduced to this branch four months after being added to the CB, with the option to defer feature upgrades as necessary for up to eight months, while still receiving security patches and critical upgrades.

This branch is reminiscent of the stable branch in Debian.

Long Term Servicing Branch (LTSB)

The LTSB, which is only available on Windows 10 Enterprise SKUs, allows for the indefinite deferral of critical updates; feature updates are only possible through the manual update of the LTSB versions. It will be possible to perform an in-place upgrade to the newest LTSB version from three versions back, and has a support period of five years mainstream, and five years extended.

In general, this branch is for use cases that require full qualification of all software, including patches, before deployment (often, for legal compliance). It also makes sense as a functional replacement for Windows Fundamentals for Legacy PCs.

And for the purpose of the comparison, the LTSB is similar to oldstable in Debian.

3: Evaluate it yourself before deploying

Like the transition from Windows 7 to Windows 8, many of the familiar settings menus have been altered, or the locations in which individual settings are available have changed. Some items are duplicated between the new Settings app and the classic Control Panel, though the behavior isn’t yet consistent. Getting to know the behavior of Windows 10 and where things are located in Settings is a needed step for day-to-day troubleshooting.

If you aren’t presently using the preview, you might want to first give it a shot in a VM; the ISO can be downloaded here, and the newly-released VirtualBox 5.0 supports Windows 10 guests rather well.

4: Double-check your driver compatibility

Windows 10 makes substantive changes to the driver model, which may make some devices incompatible with Windows 10 at launch. Alternatively, management software for affected devices may not operate as expected under Windows 10, which could be the source of headaches if mission-critical hardware is involved.

For an in-place upgrade to Windows 10, solving issues may be as simple as reinstalling affected programs. (A fresh install, while potentially time consuming, may be more beneficial long-term.) According to the release notes, users of USB-connected monitors or laptop docking stations (such as those found on ThinkPad models) will need to disconnect from those devices during installation, but they can continue to be used afterward. Of note, USB floppy drives specifically require new drivers to work with Windows 10.

5: Be mindful of system requirements

In contrast to previous versions of Windows, Windows 10 is considered a service. Microsoft’s Executive VP of Windows and Devices, Terry Myerson, explained in a blog post that Microsoft “will continue to keep it current for the supported lifetime of the device — at no cost.”

The meaning of what constitutes the “supported lifetime of a device” has not been pinned down. In an Investor Relations presentation, it was revealed that device lifetime is determined by “customer type,” and that the estimated lifetime “can range from two to four years.” Until these issues are further clarified, it may be best to continue with the currently deployed version of Windows, particularly for low-end devices with an Intel Atom or Celeron processor that originally shipped with Windows 7.

6: Be mindful of Microsoft-enforced bundling

In recognition of Windows 10 being considered a service, part of the strategy employed to generate revenue is the sale of additional services such as Office 365 and the inclusion of sponsored content, including Candy Crush Saga and MSN content apps that duplicate the function of using a browser to view the news. Fortunately, these are easy enough to uninstall.

In contrast, the search bar cannot be changed from searching Bing, and it cannot be completely removed (you can hide it, though it pops up over the taskbar when start is clicked), and removal of OneDrive requires extensive modifications.

7: Default sharing of Wi-Fi credentials could be a security risk

Wi-Fi Sense, a feature new to the desktop in Windows 10 (though it debuted in Windows Phone 8.1), shares the login credentials of protected Wi-Fi networks with Outlook.com contacts, Skype contacts, and optionally, Facebook friends. The password isn’t exposed to the user, though Microsoft will store it in the cloud. This is designed to only allow internet access, and block attempts to access other connected devices, but with the rise of consumerization and continually insisting that users not share passwords, having Windows do so automatically could be problematic.

What’s your Windows 10 migration plan?

When is your organization planning to migrate to Windows 10 (if at all)? What concerns do you have about the deployment? What Windows 10 features do you find most compelling? Share your thoughts in the comments.

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