Windows Insider Preview updates are delivered to testers in different channels (previously 'rings') or logical categories: Windows Insiders in Dev Channel (previously Fast Ring) receive updates prior to Windows Insiders in Beta Channel (previously Slow Ring) but might experience more bugs and other issues. The first Insider build for Windows 11 was released on Jfor the Dev Channel. On June 24, 2021, Microsoft announced that the program would extend to Windows 11, with the Dev and Beta channels transitioning to the new operating system. The first Insider build for this operating system was released on 13 July 2017.

In May 2017, Microsoft announced that the program would extend to Windows Server 2016.

This made the ability to install Windows Insider preview builds an optional feature which could be accessed directly from within Windows 10. With the release of Windows 10, the Windows Insider app was merged with the Settings app. They were also among the first people to receive the official update to Windows 10. By the time of the official launch of Windows 10 for PCs, a total of 5 million volunteers were registered on both Windows 10 and Windows 10 Mobile. Microsoft originally launched Windows Insider for enterprise testers and the 'technically able' to test out new developer features and to gather feedback to improve the features built into Windows 10. See also: Windows 10 version history and Windows 11 version history Similar to the Windows Insider program, the Microsoft Office, Microsoft Edge, Skype, Bing, Xbox and Visual Studio Code teams have set up their own Insider programs. The current head of the Windows Insider program is Amanda Langowski.

Gabriel Aul and Dona Sarkar were both previously the head of the Windows Insider Program. Microsoft announced that the Windows Insider program would continue beyond the official release of Windows 10 for future updates.

On February 12, 2015, Microsoft started to test out previews of Windows 10 Mobile. By September 2015, over 7 million people took part in the Windows Insider program. It was announced on Septemalong with Windows 10. Microsoft launched Windows Insider for developers, enterprise testers and the 'technically able' to test new developer features on pre-release software and builds to gather low level diagnostics feedback in order to identify, investigate, mitigate and improve the Windows 10 OS, with the help, support and guidance of the Insider program Participants, in direct communication with Microsoft Engineers via a proprietary communication and diagnostic channel. Windows Insider is an open software testing program by Microsoft that allows users who own a valid license of Windows 11, Windows 10, or Windows Server to register for pre-release builds of the operating system previously only accessible to software developers. Open software testing program by Microsoft

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