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Editing because I was really dumb.....there is no issue here.... Below is my environment information - the only thing that seems off is that I am using MacOS 11.4, not 10.16. Eddie System/Environment Report - 10/1/2021 - 3:23 AM UTC Eddie version: 2.20.0 Eddie OS build: macos_x64 Eddie architecture: x64 OS type: MacOS OS name: macOS 10.16 OS version: 10.16 (Build 20F71) OS architecture: x64 Mono /.Net Framework: v4.0.30319 TUN driver: Expected OpenVPN: 2.5.1 - OpenSSL 1.1.1j 16 Feb 2021, LZO 2.10 (/Applications/Eddie.app/Contents/MacOS/openvpn) Hummingbird: 3.3.2 - Hummingbird - AirVPN OpenVPN 3 Client 1.1.1 - 7 January 2020 (/Applications/Eddie.app/Contents/MacOS/hummingbird) SSH: OpenSSH_8.1p1, LibreSSL 2.7.3 (/usr/bin/ssh) SSL: stunnel 5.56 (/Applications/Eddie.app/Contents/MacOS/stunnel) Profile path: .config/eddie/default.profile Data path: .config/eddie Application path: /Applications/Eddie.app/Contents/MacOS Executable path: /Applications/Eddie.app/Contents/MacOS/Eddie Command line arguments: (0 args) Network Lock Active: No Connected to VPN: No Detected DNS: 2001:428::1, 2001:428::2, 192.168.0.1, 205.171.3.65