It turns out that my issue came from the difference in default behavior between a vSS (Standard Switch) and a vDS (Distributed Switch). For those that want the TL:DR -> Set all security settings to “accept”. There are three security settings for switches in VMware. Promiscuous Mode – Allows the virtual networking adapter to observer any of the traffic submitted through the vSwitch. MAC Address Changes – Allows differences in the initial MAC address and the effective MAC on incoming traffic.