What stops working after updates from Windows, Microsoft 365, Exchange, VMware, Veeam and other major vendors – with status, workaround and fix, continuously from the vendors’ official sources, complemented by reports from forums and the community and by targeted web research. Anything the vendor has not confirmed yet is labelled as a community report.
Manitoba is permanently moving to UTC-5 and will not set its clocks back on November 1, 2026. Windows devices in Manitoba are affected because their time zone data does not yet reflect this. Microsoft states a fix is releasing in October 2026 and recommends a temporary workaround for devices that cannot be updated in time.
Certificates used to establish trusted connections to Windows Update expire on May 17, 2027 and June 19, 2027. Devices without the replacement certificates will lose access to Windows Update. Most up-to-date, supported devices need no action. Devices receiving updates from WSUS (Windows Server Update Services) are not affected.
RD Web Access in Windows Server relies on XSLT (Extensible Stylesheet Language Transformations), which is being disabled in Chromium-based browsers such as Microsoft Edge and Google Chrome. Once it is disabled, the RD Web Access page fails to render and users cannot reach it. Microsoft documents workarounds and asks admins to adopt one before the browser change reaches their users.
After the Windows updates of September 22, 2026 (KB5124010) and later, some applications that need to decode AC-3 (Dolby Digital) audio might close unexpectedly. Microsoft has resolved the issue with the updates released October 13, 2026 (KB5127648) and later.
After the September 2026 preview update, non-admin users might be unable to connect via Remote Desktop to devices that have Administrator protection enabled. Microsoft resolved the issue with updates released on 2026-10-28. For Windows 11 24H2 the release health page still shows the issue as mitigated, with a fix planned for a future update.
After installing Windows 11, version 26H2 and subsequent updates, some devices may fail to load the desktop after sign-in. The issue was mainly observed on Azure Virtual Desktop (AVD) hosts using FSLogix, more often with some existing user profiles. Microsoft resolved it with the updates released on 2026-10-13 (KB5127648) and later.
The October 2026 Windows security update was released on 2026-10-13 for all supported Windows versions. For Windows 11, version 26H2, it fixes several known problems: Always On VPN, a black screen in Azure Virtual Desktop with FSLogix, and tiered Storage Spaces Direct virtual disks. A limited number of devices may need one additional restart during installation because of the Secure Boot certificate update.
From January 15, 2027, Microsoft Intune no longer supports auto-discovery of the enrollment service via the EnterpriseEnrollment DNS CNAME record in Windows MDM-only enrollment. Users may then have to enter the enrollment server URL manually. Windows MDM-only enrollment itself remains supported and existing enrolled devices are not affected.
Microsoft has released Windows updates that add new region-specific time zones for Alberta, British Columbia and Manitoba. On November 1, 2026, clocks in these provinces will not be set back by one hour. Devices without the update or the correct time zone setting might display the wrong local time.
Since the October 13, 2026 updates, Exchange servers running on affected Windows Server versions may become unstable after some time. Microsoft states this is not an Exchange update issue. A registry workaround (EpmapSavedContextCap) is available; no follow-up fix is imminent.
Microsoft has started deprecating Exchange Web Services (EWS) in Exchange Online. In the multi-tenant (WW) cloud, EWSEnabled = True alone no longer keeps EWS working; an app ID allow list (EWSAllowedAppIDs) is required. Microsoft is disabling EWS in tenants where both settings are empty. Tenants already set to EWSEnabled = True are not changed until April 2027.
We continuously read the vendors’ official sources, community reports and trade media and summarise them in our own words, with a link to the source:
Microsoft: Windows release health (Windows 10/11, Server 2016 to 2025), Windows message center, known issues of Microsoft 365 Apps (Outlook, Excel, Word, PowerPoint), Edge, Intune, Autopilot, Windows 365 and Entra Connect, Microsoft KB articles with timelines, Exchange and Windows IT Pro blogs, optionally Microsoft 365 service health and message center
other vendors: Veeam KB, Citrix (known issues), Ubuntu and Debian (regressions), Broadcom (VMware), Fortinet, Cisco, Mozilla, Let’s Encrypt
community (title, short excerpt and link only, without the names of the authors): Microsoft Q&A, Microsoft Tech Community (discussions), Veeam R&D Forums, Eleven Forum
targeted web research with AI (Claude), e.g. on the updates of the month – this also finds discussions on Reddit and in forums; such entries are labelled as community reports until the vendor confirms them
early warning from trade media (title and link only): Born’s Tech and Windows World, BleepingComputer, AskWoody, Windows Latest, Windows Central, gHacks, The Windows Club, Deskmodder, Dr. Windows, WindowsArea, Frankys Web, heise online
Summary and translation with AI (Claude by Anthropic) – without any data of visitors.
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