This is a little guide that helps you to "proxify" a VMware Fusion virtual machine on macOS. This can be useful if you want to isolate and analyse web traffic to/from an application by running it in a VM.

proxify-vmware-fusion-vm.md

Proxifying a VMware Fusion virtual machine on macOS

This is a little guide that helps you to "proxify" a VMware Fusion virtual machine on macOS. This can be useful if you want to isolate and analyse web traffic to/from an application by running it in a VM.

Prerequisites

• VMware Fusion 11 Pro
• Transparent HTTP/HTTPS proxy (e.g. Burp Suite Pro or mitmproxy)

Configure VMware command-line utilities

Not required, but helpful if you plan on using the VMware-provided command-line utilities.

• Make sure that /Applications/VMware\ Fusion.app/Contents/Library/ is in your $PATH
• Assign the path to the virtual machine to a variable: vmpath="$HOME/vms/macos-test.vmwarevm"

Networking

Configure the network

Create a new custom network through the VMware Fusion GUI app.

1. Open the network preferences: 'Preferences' > 'Network'
2. Click the plus sign to add a new custom network
3. Uncheck "Provide addresses on this network via DHCP"
4. Apply changes

You could verify it as follows:

$ vmrun listNetworkAdapters "$vmpath"

Total network adapters: 1
INDEX  TYPE         VMNET
0      custom       vmnet2

If the network adapter was not attached to the virtual machine, you could add it using the following command (the virtual machine needs to be powerd off):

vmrun addNetworkAdapter "$vmpath" custom vmnet2

Configure DHCP server

1. Install dnsmasq: brew install dnsmasq
2. Run dnsmasq (sudo dnsmasq -dC dnsmasq_vmware.conf) with the following minimal configuration:

# dnsmasq_vmware.conf

domain-needed
bogus-priv
no-poll

interface=vmnet2
listen-address=192.168.124.1

dhcp-range=192.168.124.10,192.168.124.255,96h

dhcp-option=option:router,192.168.124.1
dhcp-option=option:dns-server,192.168.124.1

Configure the host

1. Open the /etc/pf.conf file in an editor
2. Add the configuration below right after rdr-anchor "com.apple/*" (and before dummynet-anchor "com.apple/*")
3. Verify the configuration: pfctl -vnf /etc/pf.conf
4. Apply the updated configuration: sudo pfctl -ef /etc/pf.conf

nat on en1 proto { tcp, udp } from 192.168.124.0/24 to any -> (en1)
rdr on vmnet2 inet proto tcp from any to any port { 80, 443 } -> 127.0.0.1 port 8080
pass from { lo0, 192.168.124.0/24 } to any keep state

1. Enable packet forwarding: sudo sysctl net.inet.ip.forwarding=1

Proxy listening

Burp Suite Pro

1. Add a new Proxy Listener ('Proxy' > 'Options') that binds to the loopback address (127.0.0.1) on port 8080
2. Configure the Proxy Listener to use the transparent mode: edit Proxy Listener > 'Request handling' > check "Support invisible proxying"
3. Install the Burp CA certificate (available through http://burp) in the root store of the browser or OS running in the virtual machine
4. If it doesn't work right away then try to disable/enable the Proxy Listener (check/uncheck 'Running')

mitmproxy

1. mitmproxy --mode transparent --showhost
2. Install the mitmproxy CA certificate (available through http://mitm.it) in the trust store of the browser or OS running in the virtual machine