Starting with Windows Server 2012, Microsoft renamed SBS to Windows Server Essentials. The Essentials edition is a scaled down version for 1 to 25 users the other editions are based on the Windows Server codebase and include Exchange Server, Windows SharePoint Services, and Microsoft Outlook in addition to what comes with Windows Server. SBS 2011 was available in Essentials, Standard, and Premium editions.

In December 2008, Microsoft also introduced a Windows Essential Business Server product aimed at medium-sized businesses, but this was discontinued in June 2010 due to low demand. Those upgrading to SBS 2008 Premium edition via Software Assurance were compensated with a free license for the latest version of ISA Server. SBS 2008 Premium edition does not include ISA Server but includes SQL Server 2008. This edition of Windows Server 2008 is available outside the product suite, supporting a maximum of 15 Client Access Licenses. SBS 2008 came with an edition of Windows Server 2008 bears the name Windows Server 2008 for Windows Essential Server Solutions ('WinWESS'), also known as Windows Server 2008 Standard FE. SBS 2003 and later all bear the 'Windows' brand and are editions of Windows Server. Until this point, the Premium editions of SBS included SQL Server, ISA Server, and FrontPage. With the release of Windows 2000, however, Microsoft spun off Small Business Server 2000 as a separate offering. Initially, Microsoft marketed the Small Business Server (SBS) an edition of Microsoft BackOffice Server. Those holding an 'Essentials' license receive an activation key for Windows Server 2022 instead.

Microsoft has since discontinued this suite in favor of Microsoft 365 and Microsoft Azure. Windows Server Essentials 2019 was the last release of this product. Application server technologies are tightly integrated to provide and offer management benefits such as integrated setup, enhanced monitoring, Remote Web Workplace, a unified management console, and remote access. It includes Windows Server, Exchange Server, Windows SharePoint Services, and Microsoft Outlook. Windows Server Essentials (formerly Small Business Server or SBS) is an integrated server suite from Microsoft for businesses with no more than 25 users or 50 devices.

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