OpenVPN / OpenVPN/openvpn

Issue with OpenVPN-2.6.14-I002.msi-2.6.14-I004.msi establishing tunnel to Azure Gateway (only on Surface Pro 2-in-1s)

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@lstipakov is already working on this.

Since Sep 14, 2025.

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Description

UPDATE 8/28/2025: Still occurring with OpenVPN-2.6.14-I004.msi.

IMPORTANT NOTE
Bugs about OpenVPN Access Server, OpenVPN Connect or any other product by OpenVPN Inc. should be directly reported to OpenVPN Inc. at https://support.openvpn.net

Describe the bug
OpenVPN starting at version 2.6.14-I002 (amd64) (arm64 for Snapdragon Surface Pros) fails to establish a tunnel to Azure Gateway, only on Surface Pros 7+, 10s, 11s.****

To Reproduce
Install OpenVPN-2.6.14-I002-amd64.msi to Surface Pro 7+, 10 (OR OpenVPN-2.6.14-I002-arm64.msi to Surface Pro 11s) and previously working tunnel (on ver 2.6.14-I001-amd64/arm64.msi) will fail to connect to an Azure Gateway. Settings on the clients include DCO disabled.**

Expected behavior
Tunnel should be established with Azure Gateway.

Version information (please complete the following information):

  • OS: Windows 11 24H2 (Build 26100.4770)
  • OpenVPN version: 2.6.14-I002 (amd64) (arm64)
  • Repeat for peer if relevant

Additional context
OpenVPN 2.6.14-I0002 works as expected on all other workstations, except Surface Pros in the tenant. The issue persists after network resets. Unfortunately, I cannot provide much logging information from the Azure Gateway side, as the logging surrounding their Gateways is rather limited. I have temporarily rolled back to 2.6.14-I001 on Surface Pros.

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