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 at 8:03 PM.

  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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