We should remember Chris Jackson and his compatibility cookbook. Chris started an entire industry with a good idea. How to help large organizations migrate faster, with less risk. I think that the first version of the Cookbook was released in 2008 and addressed the challenge of moving from Windows XP to Windows 7 – where compatibility was a major challenge.

Windows 10 and Windows 11 are now the most compatible platforms available from Microsoft with an internal engineering focus that now includes:

  • Application Telemetry
  • ISV Partnership ecosystems (like Readiness)
  • Improved handling of API changes
  • Improved version flighting and better feedback loops

Things are definitely better, and migrations have been relatively smooth over the past few years. That said, some technical debt has crept into the migration challenge with several significant changes introduced over the past few minor iterations of Windows, culminating in a significant compatibility challenge when moving to Windows 11 23H2.

I have included a short list of some the challenges that most users will have to manage when delivering the latest build from Microsoft (Windows 11 223H2).

Tips The Tips app is deprecated and will be removed in a future release of Windows. Content in the app will continue to be updated with information about new Windows features until the app is removed.
Computer Browser The Computer Browser driver and service are deprecated. The browser (browser protocol and service) is a dated and insecure device location protocol. This protocol, service, and driver were first disabled by default in Windows 10 with the removal of the SMB1 service.
Webclient (WebDAV) Service The Webclient (WebDAV) service is deprecated. The Webclient service isn’t started by default in Windows. For more information on WebDAV, see WebDAV – Win32 apps.
Remote Mailslots Remote Mailslots are deprecated. The Remote Mailslot protocol is a dated, simple, unreliable, insecure IPC method first introduced in MS DOS. This protocol was first disabled by default in Windows 11 Insider Preview Build .
Timeline for Microsoft Entra accounts Cross-device syncing of Microsoft Entra user activity history will stop starting in January 2024. Microsoft will stop storing this data in the cloud, aligning with the previous change for Microsoft accounts (MSA) in 2021.
VBScript VBScript is deprecated. In future releases of Windows, VBScript will be available as a feature on demand before its removal from the operating system.
WordPad WordPad is no longer being updated and will be removed in a future release of Windows. We recommend Microsoft Word for rich text documents like .doc and .rtf and Windows Notepad for plain text documents like .txt.
AllJoyn Microsoft’s implementation of AllJoyn which included the Windows.Devices.AllJoyn API namespace, a Win32 API, a management configuration service provider (CSP), and an Alljoyn Router Service has been deprecated. AllJoyn, sponsored by AllSeen Alliance, was an open source discovery and communication protocol for Internet of Things scenarios such as turning on/off lights or reading temperatures.
TLS 1.0 and 1.1 Over the past several years, internet standards and regulatory bodies have deprecated or disallowed TLS versions 1.0 and 1.1 due to various security issues. Starting in Windows 11 Insider Preview builds for September 2023 and continuing in future Windows OS releases, TLS 1.0 and 1.1 will be disabled by default.
Cortana in Windows Cortana in Windows as a standalone app is deprecated. This change only impacts Cortana in Windows not some of the web based tools such as Outlook for the Web

Readiness offers automated algorithmic checks to ensure that each application installation correctly installs, updates, run as expected and then completely/cleanly uninstalls. Automated testing will help with these scenarios (especially a testing platform that offers a “delta” or comparison between builds).

However, for your line of business applications getting the application owner (doing UAT) to test and approve the testing results is still absolutely essential.

Try the Readiness Unbound offer to get started today.

Greg Lambert