Scenario: Host MacOS is connected to Cisco AnyConnect VPN but using the recommended "Shared Network" option, the Kali Linux doesn't have any network connectivity. Virtual Machine Type: Kali Linux 1. Network adapter: Shared Network (Recommended) Result: Doesn't establish connectivity and no IP is assigned to the VM. 2. Network adapter: Bridged Default Adapter Result: Assigned an IP and connects successfully to local subnet. No connectivity into the Cisco AnyConnect VPN subnet. The below links show support for Windows operating systems but I cannot find troubleshooting procedures for Linux VMs that are experiencing this issue. https://kb.parallels.com/4948 https://forum.parallels.com/threads/cisco-vpn-connection.289914/ https://kb.parallels.com/8978 https://kb.parallels.com/123071