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It took me nearly two full days of going down the deepest network rabbit hole to figure this one out, so I'll share my solution to save other people the time.

Asterisk Add-On Configuration

In the pjsip_custom.conf file add this section:

[transport-udp]
type=transport
protocol=udp
bind=0.0.0.0:5060  ; Binds to all IP addresses on port 5060
; --- Network and NAT Configuration ---
; This is the most critical part for your use case.
; Add your local LAN and the VPN subnet here.
; Asterisk will treat any traffic from these networks as internal.
local_net=192.168.1.0/24   ; Your main LAN subnet - CHANGE THIS IF YOU USE A DIFFERENT NETWORK
local_net=172.27.66.0/24   ; The VPN clients virtual add…

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