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

Y

YvonnieM

Bit poster
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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