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Lessons learned upgrading Windows 10 to a new version; finding incompatible applications

This post is part of a series covering lessons learned when upgrading Windows 10 to a new version (Microsoft releases a new version twice a year). It is based on our own experiences upgrading over 25,000 machines.

Find incompatible apps using a phased deployment and pilot groups

While there are tools that help indicate application compatibility we have found they contain too many false positives (apps indicated as an issue, or potential issue that work just fine), too many false negatives (apps indicated as fine, that are not fine), and a general overwhelming amount of data (consider an organisation with 5,000+ users can easily have 5,000+ applications; this sounds improbable, but in organisation where application versions are fragmented it is possible to have 10+ versions of each application thus it quickly adds up).

In our experience, the actual applications with an issue after version upgrade is insignificantly small. Indeed, in deployments covering over 25,000 machines, we have found just 3 applications in total.

Given the above, we have found deploying an upgrade using a phased deployment and pilot groups to be the most time effective way to identify applications, while at the same time piloting the deployment approach. Yes, this is a reactive approach to identifying applications, but it is also relatively pragmatic.

An example phased approach:

  • First phase – Core apps: Deploy to owners of core applications in your Windows image; Antivirus, VPN, SAP, etc.
  • Second phase – Support teams: Deploy to site support and application support teams. This is key in gaining support visibility before extending to the next phases. As part of this second phase, support processes should be provided to on how to roll back an upgrade or restart a failed upgrade.
  • Third phase – All of IT: This phase allows any kinks in deployment to be identified before deploying to your Business Unit first adopters; this is important so that any issues are genuine application issues and not issues due to problems with the deployment process.
  • Forth phase – Business Unit first adopters: Deploy to owners of key business systems; Finance, Legal, HR, and whatever makes sense in your organisation. This is easy in organisations that have clear representatives for key groups along with a helpful attitude for supporting technology upgrades.
  • Fifth phase – Full rollout: By the time this phase starts any significant application issues will have been identified. Of course, there still may be application issues waiting to be found, but if the first four phases were completed correctly the only applications with issues can be managed re-actively without significant impact.

The above approach not only finds incompatible applications without any significant impact, but it also enables effective engagement with support teams and users which facilitates support for a full rollout.

2020-01-17T12:34:14+00:00Categories: Uncategorized|

Windows and Office 365 news roundup 13th January 2020

A happy new year and welcome to our first news roundup for 2020! Microsoft has started the year with various announcements covering: Excel on the web; details on the pending release of the new Edge browser; and, Microsoft Teams incorporation into Office 365 deployment media. There is also some unofficial news about Microsoft Store for Business and news from CES tradeshow on new dual-screen devices. (more…)

Windows and Office 365 news roundup 23rd December 2019

A flurry of announcements as we head into Xmas covering: Azure AD user provisioning; visual search; Your Phone app and Android integration; some “under the hood” information on Azure AD; new phone sign-in feature for Azure AD B2C; and migration options from Office 365 Video to Microsoft Streams. (more…)

Windows and Office 365 weekly news roundup – 11 November 2019

The FIDO2 security key from Yubikey enabling passwordless experience, now available with AzureAD Hybrid joined devices

In the last week there have been many announcements from Microsoft at the annual Ignite conference covering: the release date for the new Microsoft Edge; changes to combined SCCM and Intune under the Microsoft Endpoint Manager brand amongst other SCCM and Intune capability announcements; new Microsoft solution to automate Knowledge Management; new passwordless capabilities for AzureAD Hybrid joined devices; and, a review of the Surface Pro 7. (more…)

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