BEGIN:VCALENDAR VERSION:2.0 PRODID:-//KBY Technologies//Admin Deadlines//EN CALSCALE:GREGORIAN METHOD:PUBLISH X-WR-CALNAME:KBY admin deadlines (Windows Server\, Active Directory) X-WR-CALDESC:Microsoft and Apple retirements\, deprecations\, enforcement d ates and end-of-support dates for endpoint and identity admins. Each date is quoted from the vendor's own page. X-WR-TIMEZONE:UTC REFRESH-INTERVAL;VALUE=DURATION:P1D X-PUBLISHED-TTL:P1D URL;VALUE=URI:https://www.kbytechnologies.com/deadlines BEGIN:VEVENT UID:entra-connect-block-hard-match-privileged-users@kbytechnologies.com DTSTAMP:20261109T000000Z LAST-MODIFIED:20261109T000000Z DTSTART;VALUE=DATE:20260601 DTEND;VALUE=DATE:20260602 SUMMARY:Entra Connect and Cloud Sync blocked from hard-matching users who h old Entra roles DESCRIPTION:Microsoft · Enforcement\n\nWho is affected: Hybrid identity te ams that hard-match new Active Directory users to existing cloud users. Ma tching is now refused when the cloud user holds a Microsoft Entra role\; s oft match and existing synced users are not affected.\n\nWhat to do:\n1. R emove Entra role assignments from a cloud user before you hard-match it\, then reassign them.\n2. Check sync error reports for hard-match failures s ince June 2026.\n3. Keep privileged admin accounts cloud-only rather than synced from Active Directory.\n\nSources:\n- Microsoft Entra releases and announcements (Microsoft Learn): https://learn.microsoft.com/en-us/entra/f undamentals/whats-new\n "Beginning June 1\, 2026\, Microsoft Entra ID wil l block any attempt by Entra Connect Sync or Cloud Sync from hard-matching a new user object from Active Directory to an existing cloud-managed Entr a ID user object that holds Microsoft Entra roles."\n\nChecked 2026-11-09. Dates move\; check the source before you act.\nhttps://www.kbytechnologie s.com/deadlines/entra-connect-block-hard-match-privileged-users URL;VALUE=URI:https://www.kbytechnologies.com/deadlines/entra-connect-block -hard-match-privileged-users CATEGORIES:Microsoft,Enforcement TRANSP:TRANSPARENT STATUS:CONFIRMED END:VEVENT BEGIN:VEVENT UID:secure-boot-2011-kek-and-uefi-ca-expiry@kbytechnologies.com DTSTAMP:20261109T000000Z LAST-MODIFIED:20261109T000000Z DTSTART;VALUE=DATE:20260624 DTEND;VALUE=DATE:20260625 SUMMARY:Secure Boot 2011 certificates start expiring (KEK CA 2011 and UEFI CA 2011) DESCRIPTION:Microsoft · End of support\n\nWho is affected: Windows PCs\, s ervers and virtual machines with Secure Boot that do not yet have the 2023 certificates. They keep booting\, but cannot apply future Secure Boot upd ates signed with the new authorities.\n\nWhat to do:\n1. Check certificate status per device\, for example with the Secure Boot status report in Win dows Autopatch.\n2. Keep devices on current monthly updates\, which delive r the new certificates in phases.\n3. Ask OEMs and hypervisor vendors for firmware or template updates where the update cannot apply.\n\nSources:\n- Manage Secure Boot certificate updates (Microsoft Learn): https://learn.m icrosoft.com/en-us/azure-stack/operator/secure-boot-certificates?view=azs- 2604\n "Microsoft Corporation KEK CA 2011 | June 24\, 2026 | Microsoft Co rporation KEK 2K CA 2023 | Stored in KEK | Signs updates to DB and DBX."\n - Manage Secure Boot certificate updates (Microsoft Learn): https://learn. microsoft.com/en-us/azure-stack/operator/secure-boot-certificates?view=azs -2604\n "Microsoft UEFI CA 2011 * | June 27\, 2026 | Microsoft UEFI CA 20 23 | Stored in DB | Signs third-party boot loaders and EFI applications."\ n- Windows message center (Windows release health\, Microsoft Learn): http s://learn.microsoft.com/en-us/windows/release-health/windows-message-cente r\n "Secure Boot certificates start expiring in June of 2026."\n\nChecked 2026-11-09. Dates move\; check the source before you act.\nhttps://www.kb ytechnologies.com/deadlines/secure-boot-2011-kek-and-uefi-ca-expiry URL;VALUE=URI:https://www.kbytechnologies.com/deadlines/secure-boot-2011-ke k-and-uefi-ca-expiry CATEGORIES:Microsoft,End of support TRANSP:TRANSPARENT STATUS:CONFIRMED END:VEVENT BEGIN:VEVENT UID:windows-kerberos-rc4-enforcement@kbytechnologies.com DTSTAMP:20261109T000000Z LAST-MODIFIED:20261109T000000Z DTSTART;VALUE=DATE:20260701 DTEND;VALUE=DATE:20260702 SUMMARY:Kerberos RC4 protections move to enforcement on domain controllers (July 2026) DESCRIPTION:Date: July 2026. The vendor has not published an exact day\, so this event sits on the first day of that month.\n\nMicrosoft · Enforceme nt\n\nWho is affected: Active Directory domains with service accounts or a pplications that still depend on RC4 Kerberos tickets. Audit mode and the temporary rollback registry setting were removed with this update.\n\nWhat to do:\n1. Review domain controller events for service tickets still requ ested with RC4.\n2. Enable AES on the affected service accounts and reset their passwords so AES keys exist.\n3. Retire or upgrade applications and appliances that cannot use AES.\n\nSources:\n- Windows message center (Win dows release health\, Microsoft Learn): https://learn.microsoft.com/en-us/ windows/release-health/windows-message-center\n "The July 2026 Windows se curity update enables Enforcement mode across Windows domain controllers f or Kerberos RC4 protections related to CVE‑2026‑20833."\n\nChecked 202 6-11-09. Dates move\; check the source before you act.\nhttps://www.kbytec hnologies.com/deadlines/windows-kerberos-rc4-enforcement URL;VALUE=URI:https://www.kbytechnologies.com/deadlines/windows-kerberos-rc 4-enforcement CATEGORIES:Microsoft,Enforcement TRANSP:TRANSPARENT STATUS:CONFIRMED END:VEVENT BEGIN:VEVENT UID:windows-ntlmv1-sso-hardening@kbytechnologies.com DTSTAMP:20261109T000000Z LAST-MODIFIED:20261109T000000Z DTSTART;VALUE=DATE:20261001 DTEND;VALUE=DATE:20261002 SUMMARY:NTLMv1-derived credentials for single sign-on restricted by default (October 2026) DESCRIPTION:Date: October 2026. The vendor has not published an exact day\, so this event sits on the first day of that month.\n\nMicrosoft · Enforc ement\n\nWho is affected: Windows 11 (24H2\, 25H2\, 26H2) and Windows Serv er 2025 devices with Credential Guard disabled that connect to Wi-Fi\, Eth ernet or VPN using MS-CHAPv2. Single sign-on to those networks can fail.\n \nWhat to do:\n1. Find Wi-Fi\, wired 802.1X and VPN profiles that use MS-C HAPv2 (PEAP-MSCHAPv2).\n2. Move them to certificate-based authentication\, for example EAP-TLS with Intune-issued certificates.\n3. Use the temporar y allow-and-audit registry setting in KB5066470 only while you migrate.\n\ nSources:\n- Windows message center (Windows release health\, Microsoft Le arn): https://learn.microsoft.com/en-us/windows/release-health/windows-mes sage-center\n "Beginning with the October 2026 security update\, Windows 11\, versions 26H2\, 25H2\, and 24H2\, along with Windows Server 2025\, en force restrictions on generating NTLMv1-derived credentials for Single Sig n-On by default."\n\nChecked 2026-11-09. Dates move\; check the source bef ore you act.\nhttps://www.kbytechnologies.com/deadlines/windows-ntlmv1-sso -hardening URL;VALUE=URI:https://www.kbytechnologies.com/deadlines/windows-ntlmv1-sso- hardening CATEGORIES:Microsoft,Enforcement TRANSP:TRANSPARENT STATUS:CONFIRMED END:VEVENT BEGIN:VEVENT UID:secure-boot-windows-production-pca-2011-expiry@kbytechnologies.com DTSTAMP:20261109T000000Z LAST-MODIFIED:20261109T000000Z DTSTART;VALUE=DATE:20261019 DTEND;VALUE=DATE:20261020 SUMMARY:Secure Boot: Microsoft Windows Production PCA 2011 expires DESCRIPTION:Microsoft · End of support\n\nWho is affected: Windows devices whose boot manager still relies on the 2011 Windows Production PCA. The r eplacement is Windows UEFI CA 2023\, which signs the Windows boot loader.\ n\nWhat to do:\n1. Confirm devices report the Windows UEFI CA 2023 certifi cate in the Secure Boot database.\n2. Expect one extra restart on some dev ices when the Secure Boot certificate update applies.\n3. Refresh boot med ia\, PXE images and VM templates so they boot with the new certificate cha in.\n\nSources:\n- Manage Secure Boot certificate updates (Microsoft Learn ): https://learn.microsoft.com/en-us/azure-stack/operator/secure-boot-cert ificates?view=azs-2604\n "Microsoft Windows Production PCA 2011 | October 19\, 2026 | Windows UEFI CA 2023 | Stored in DB | Used for signing the Wi ndows boot loader."\n\nChecked 2026-11-09. Dates move\; check the source b efore you act.\nhttps://www.kbytechnologies.com/deadlines/secure-boot-wind ows-production-pca-2011-expiry URL;VALUE=URI:https://www.kbytechnologies.com/deadlines/secure-boot-windows -production-pca-2011-expiry CATEGORIES:Microsoft,End of support TRANSP:TRANSPARENT STATUS:CONFIRMED END:VEVENT BEGIN:VEVENT UID:windows-refs-removable-media-enforcement@kbytechnologies.com DTSTAMP:20261109T000000Z LAST-MODIFIED:20261109T000000Z DTSTART;VALUE=DATE:20270101 DTEND;VALUE=DATE:20270102 SUMMARY:ReFS volumes on removable media: enforcement phase (January 2027) DESCRIPTION:Date: January 2027. The vendor has not published an exact day\, so this event sits on the first day of that month.\n\nMicrosoft · Enforc ement\n\nWho is affected: Devices that use ReFS on externally attached or removable storage. The October 2026 update started the audit phase\; the J anuary 2027 update can block affected volumes.\n\nWhat to do:\n1. Review t he audit events added by the October 2026 update to find external ReFS vol umes.\n2. Reformat or move data off unsupported external ReFS configuratio ns before January 2027.\n\nSources:\n- Windows message center (Windows rel ease health\, Microsoft Learn): https://learn.microsoft.com/en-us/windows/ release-health/windows-message-center\n "January 2027 Windows security up date (Enforcement phase)"\n\nChecked 2026-11-09. Dates move\; check the so urce before you act.\nhttps://www.kbytechnologies.com/deadlines/windows-re fs-removable-media-enforcement URL;VALUE=URI:https://www.kbytechnologies.com/deadlines/windows-refs-remova ble-media-enforcement CATEGORIES:Microsoft,Enforcement TRANSP:TRANSPARENT STATUS:CONFIRMED END:VEVENT BEGIN:VEVENT UID:windows-server-2016-end@kbytechnologies.com DTSTAMP:20261109T000000Z LAST-MODIFIED:20261109T000000Z DTSTART;VALUE=DATE:20270112 DTEND;VALUE=DATE:20270113 SUMMARY:Windows Server 2016 (and WSUS on it) reaches end of updates DESCRIPTION:Microsoft · End of support\n\nWho is affected: All editions of Windows Server 2016\, including servers that host WSUS\, Configuration Ma nager site roles\, certificate services or other endpoint management infra structure.\n\nWhat to do:\n1. List Windows Server 2016 machines that suppo rt endpoint management (WSUS\, distribution points\, NDES\, connectors).\n 2. Rebuild or upgrade them to Windows Server 2025.\n3. Buy ESU for Standar d and Datacenter servers that cannot move in time.\n\nSources:\n- Windows message center (Windows release health\, Microsoft Learn): https://learn.m icrosoft.com/en-us/windows/release-health/windows-message-center\n "On Ja nuary 12\, 2027\, Windows Server 2016 will reach end of updates."\n- Endin g Support in 2027 (Microsoft Lifecycle): https://learn.microsoft.com/en-us /lifecycle/end-of-support/end-of-support-2027\n "Windows Server 2016 | Wi ndows Server Update Services for Windows Server 2016 | January 12\, 2027"\ n\nChecked 2026-11-09. Dates move\; check the source before you act.\nhttp s://www.kbytechnologies.com/deadlines/windows-server-2016-end URL;VALUE=URI:https://www.kbytechnologies.com/deadlines/windows-server-2016 -end CATEGORIES:Microsoft,End of support TRANSP:TRANSPARENT STATUS:CONFIRMED END:VEVENT BEGIN:VEVENT UID:entra-connect-sync-2-5-190-end@kbytechnologies.com DTSTAMP:20261109T000000Z LAST-MODIFIED:20261109T000000Z DTSTART;VALUE=DATE:20270202 DTEND;VALUE=DATE:20270203 SUMMARY:Entra Connect Sync 2.5.190.0 reaches end of support DESCRIPTION:Microsoft · End of support\n\nWho is affected: Sync servers st ill on Entra Connect Sync 2.5.190.0. Version 2.6.1.0 follows on 10 Mar 202 7\; each 2.x version retires 12 months after a newer one is released.\n\nW hat to do:\n1. Upgrade to the latest Entra Connect Sync release from the M icrosoft Entra admin center.\n2. If you edited miiserver.exe.config\, chec k the known upgrade issue on the version history page first.\n\nSources:\n - Microsoft Entra Connect: Version release history (Microsoft Learn): http s://learn.microsoft.com/en-us/entra/identity/hybrid/connect/reference-conn ect-version-history\n "2.5.190.0 | 02 Feb 2027 (12 months after release o f 2.6.1.0) | 19 Nov 2025"\n- Microsoft Entra Connect: Version release hist ory (Microsoft Learn): https://learn.microsoft.com/en-us/entra/identity/hy brid/connect/reference-connect-version-history\n "2.6.1.0 | 10 Mar 2027 ( 12 months after release of 2.6.3.0) | 2 Feb 2026"\n\nChecked 2026-11-09. D ates move\; check the source before you act.\nhttps://www.kbytechnologies. com/deadlines/entra-connect-sync-2-5-190-end URL;VALUE=URI:https://www.kbytechnologies.com/deadlines/entra-connect-sync- 2-5-190-end CATEGORIES:Microsoft,End of support TRANSP:TRANSPARENT STATUS:CONFIRMED END:VEVENT BEGIN:VEVENT UID:entra-connect-sync-application-authentication-required@kbytechnologies. com DTSTAMP:20261109T000000Z LAST-MODIFIED:20261109T000000Z DTSTART;VALUE=DATE:20270407 DTEND;VALUE=DATE:20270408 SUMMARY:Entra Connect Sync: upgrade to 2.6.84.0 or later and use applicatio n-based authentication DESCRIPTION:Microsoft · Enforcement\n\nWho is affected: Every organisation running Microsoft Entra Connect Sync. Synchronisation stops after this da te on servers that have not been upgraded and switched to application-base d authentication.\n\nWhat to do:\n1. Check the installed Entra Connect Syn c version on every sync server\, including staging servers.\n2. Download t he current build from the Microsoft Entra admin center and upgrade.\n3. Co nfigure application-based authentication and confirm .NET Framework 4.7.2 and TLS 1.2 are in place.\n\nSources:\n- Microsoft Entra Connect: Version release history (Microsoft Learn): https://learn.microsoft.com/en-us/entra /identity/hybrid/connect/reference-connect-version-history\n "Mandatory u pgrade required: Upgrade Microsoft Entra Connect Sync to version 2.6.84.0 or later and configure application-based authentication by April 7\, 2027. "\n\nChecked 2026-11-09. Dates move\; check the source before you act.\nht tps://www.kbytechnologies.com/deadlines/entra-connect-sync-application-aut hentication-required URL;VALUE=URI:https://www.kbytechnologies.com/deadlines/entra-connect-sync- application-authentication-required CATEGORIES:Microsoft,Enforcement TRANSP:TRANSPARENT STATUS:CONFIRMED END:VEVENT BEGIN:VEVENT UID:windows-update-certificate-rotation-may-2027@kbytechnologies.com DTSTAMP:20261109T000000Z LAST-MODIFIED:20261109T000000Z DTSTART;VALUE=DATE:20270517 DTEND;VALUE=DATE:20270518 SUMMARY:Windows Update certificate rotation: Windows 10 Enterprise 2019 LTS C\, Windows Server 2019 and 2016 DESCRIPTION:Microsoft · Enforcement\n\nWho is affected: Windows 10 Enterpr ise 2019 LTSC\, Windows Server 2019 and Windows Server 2016 devices that g et updates directly from Windows Update. Devices updated through WSUS are not affected by this change.\n\nWhat to do:\n1. Install the July 2026 secu rity update or later on these devices before May 17\, 2027.\n2. Find devic es that have stopped patching: without the replacement certificates they l ose access to Windows Update.\n\nSources:\n- Windows message center (Windo ws release health\, Microsoft Learn): https://learn.microsoft.com/en-us/wi ndows/release-health/windows-message-center\n "Windows 10 Enterprise 2019 LTSC\, Windows Server 2019\, and Windows Server 2016: Install the July 20 26 security update or later before May 17\, 2027."\n\nChecked 2026-11-09. Dates move\; check the source before you act.\nhttps://www.kbytechnologies .com/deadlines/windows-update-certificate-rotation-may-2027 URL;VALUE=URI:https://www.kbytechnologies.com/deadlines/windows-update-cert ificate-rotation-may-2027 CATEGORIES:Microsoft,Enforcement TRANSP:TRANSPARENT STATUS:CONFIRMED END:VEVENT BEGIN:VEVENT UID:windows-update-certificate-rotation-june-2027@kbytechnologies.com DTSTAMP:20261109T000000Z LAST-MODIFIED:20261109T000000Z DTSTART;VALUE=DATE:20270619 DTEND;VALUE=DATE:20270620 SUMMARY:Windows Update certificate rotation: Windows 11\, Windows Server 20 22/2025 and other in-support Windows 10 DESCRIPTION:Microsoft · Enforcement\n\nWho is affected: In-support Windows 11\, Windows Server 2022 and 2025\, and in-support Windows 10 devices tha t are behind on monthly updates. Windows 11\, version 25H2 and later need no action.\n\nWhat to do:\n1. Windows 11\, version 24H2 and Windows Server 2025: install the September 2025 security update or later.\n2. Other in-s upport Windows 11\, Windows Server 2022 and Windows 10: install the July 2 026 security update or later.\n3. Upgrade any out-of-support Windows versi on\, which will lose access to Windows Update.\n\nSources:\n- Windows mess age center (Windows release health\, Microsoft Learn): https://learn.micro soft.com/en-us/windows/release-health/windows-message-center\n "Certifica tes used to establish trusted connections to Windows Update will expire on May 17\, 2027 and June 19\, 2027. Devices must contain the replacement ce rtificates to continue receiving updates after the applicable expiration d ate."\n\nChecked 2026-11-09. Dates move\; check the source before you act. \nhttps://www.kbytechnologies.com/deadlines/windows-update-certificate-rot ation-june-2027 URL;VALUE=URI:https://www.kbytechnologies.com/deadlines/windows-update-cert ificate-rotation-june-2027 CATEGORIES:Microsoft,Enforcement TRANSP:TRANSPARENT STATUS:CONFIRMED END:VEVENT END:VCALENDAR