TLDR: No DHCP offers from pfsense with VLAN tagged on a VLAN-aware host. Switch is trunked to allow "All" traffic.
I have a VLAN tagged as 20: https://i.imgur.com/Rz61DMz.png
And its corresponding interface: https://i.imgur.com/pQxJitG.png
And its DHCP server: https://i.imgur.com/jsAjxid.png
I start packet capture to see if DHCP on this VLAN responds: https://i.imgur.com/xlfsm4U.png at Diagnostics -> Packet Capture -> VLAN20 (vmx1.20) (I don't see any...
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