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Always On VPN

Microsoft: September Windows updates break Always On VPN connections
Winsage
September 24, 2026

Microsoft: September Windows updates break Always On VPN connections

Microsoft has informed IT administrators about potential connection challenges with the Always On VPN after the September 2026 Windows 11 security updates. Users may face difficulties connecting to their organization's network, particularly if the VPN is set to automatically attempt an alternative connection method upon failure. Symptoms include connections remaining in a 'Connecting' state or displaying the error message: 'The specified port is already in use.' Affected versions include Windows 11, version 26H1 (KB5124012), version 25H2 (KB5124008), and version 24H2 (KB5124008). A temporary workaround involves adjusting the Always On VPN profile from automatic protocol selection to a single protocol (SSTP or IKEv2). Microsoft is also addressing various other issues related to Hyper-V, Remote Desktop Services, USB audio, and the File History backup feature.
Microsoft deprecates Windows DirectAccess, recommends Always On VPN
Winsage
June 12, 2024

Microsoft deprecates Windows DirectAccess, recommends Always On VPN

Microsoft has announced the deprecation of DirectAccess and advises users to migrate to Always On VPN as soon as possible to avoid downtime or issues. Microsoft has published a migration guide with a phased approach for an easier transition, including setting up the Always On VPN infrastructure alongside DirectAccess. The guide includes details on issuing certifications, deploying VPN configurations, Intune management, and monitoring via Microsoft Endpoint Configuration Manager. After migration, admins should remove the DirectAccess server role, update DNS records, and decommission the server from Active Directory Domain Services.
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