Azure P2S VPN (certificate) not injecting routes in Windows 11 ARM VM

Discussion in 'Parallels Desktop on a Mac with Apple silicon' started by JAIROB1, Mar 27, 2026.

  1. JAIROB1

    JAIROB1

    Messages:
    1
    Hi,

    I am running Windows 11 ARM on Parallels Desktop (Mac Apple Silicon) and having issues with an Azure Point-to-Site VPN (certificate-based).

    Setup:
    - Parallels Desktop on macOS
    - Windows 11 ARM VM
    - Network mode: Shared (NAT)
    - VPN installed using VpnClientSetupAmd64.exe
    - Certificate (.pfx) installed correctly

    Issue:
    The VPN appears to connect, but no routes are injected into the routing table.
    Running "route print" only shows the Parallels NAT network (10.211.x.x), and no Azure VNet routes are added.

    As a result, I cannot access any Azure private resources.

    Additional info:
    - The same VPN works correctly on a physical Windows machine
    - Bridged mode does not work in my network (VM gets 169.254.x.x IP)
    - No additional network interface appears after connecting

    Question:
    Is this a known limitation of Windows 11 ARM networking in Parallels when using VPN clients (IKEv2 / RAS)?
    Has anyone found a workaround?

    Thanks in advance.
     

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