VPN Not Routing to Windows VM via Parallels (Works in UTM)

Discussion in 'Installation and Configuration of Parallels Desktop' started by YvonnieM, Jun 17, 2025.

  1. YvonnieM

    YvonnieM Bit poster

    Messages:
    1
    Hi! I'm experiencing an issue with VPN passthrough on my macOS host when using Parallels Desktop (latest version) to run a Windows 11 VM.
    PROBLEM:
    I use the AWS VPN Client on my macOS host to connect to a secure internal network.
    • On macOS, the VPN connects successfully and I can access internal resources.
    • However, inside the Parallels Windows VM, I cannot access VPN-protected resources, even though the host is connected to VPN.
    Curiously, this does work perfectly on my UTM VM (on the same Mac) using an emulated VLAN network setting -- the VPN routes traffic correctly there.
    MY SETUP:
    • Host: macOS (Sonoma)
    • VM 1 (Parallels): Windows 11, Bridged Network set to Wi-Fi
    • VM 2 (UTM): Ubuntu, Network set as "Emulated VLAN"
    • VPN client: AWS VPN Client installed and configured only on the Mac host
    What I've Tried:
    1. Changed Parallels network mode to Bridged → Wi-Fi
      ⛔ Did not help.
    2. Switched to Shared Network in Parallels
      ⛔ Still can't access VPN-only URLs.
    3. Tested DNS resolution via nslookup and dig
      • Works on Mac host.
      • Times out in Windows VM.
    4. Ran VPN client inside Windows (in Parallels)
      • Installed AWS VPN Client and imported same config.
      • ⛔ VPN fails to connect (no detailed error).
    5. Tried creating a route add manually or forcing DNS resolution via hosts file
      ⛔ No success -- DNS resolution and routing fail.
    What I Suspect:
    • The VPN DNS and routing config isn't propagating to Parallels VM, even in Bridged mode.
    • UTM's Emulated VLAN mode somehow picks up the VPN routing table/DNS, but Parallels doesn't.
    What I Need:
    • Advice on how to get the Windows VM to route through the host VPN connection, or
    • A way to replicate what UTM's Emulated VLAN is doing in Parallels.
    Any help would be greatly appreciated!
     

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