Waiting for server response when setting up VPN with Orbi on MacOS

[basic]

I'm trying to connect to a VPN for work through my Orbi. I've followed the OpenVPN instructions using Tunnelbrick. When I do that I am never able to successfully connect to a server. It shows me this screen: 

The only errors that I'm seeing in the logs are: 

2022-01-31 16:01:47.983220 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
2022-01-31 16:01:47.983270 TLS Error: TLS handshake failed

Is there some other setting on the Orbi that I can change to get this VPN working?

[FURRYe38 · Accepted solution]

Your ISP Modem already has a built in router and wifi. This would be a double NAT (two router) condition which isn't recommended. https://kb.netgear.com/30186/What-is-Double-NAT
https://kb.netgear.com/30187/How-to-fix-issues-with-Double-NAT
Couple of options,
1. Configure the modem for transparent bridge or modem only mode. Then use the Orbi router in router mode. You'll need to contact the ISP for help and information in regards to the modem being bridged correctly.
2. If you can't bridge the modem, disable ALL wifi radios on the modem, configure the modems DMZ/ExposedHost or IP Pass-Through for the IP address the Orbi router gets from the modem. Then you can use the Orbi router in Router mode.
3. Or disable all wifi radios on the modem and connect the Orbi router to the modem, configure AP mode on the Orbi router. https://kb.netgear.com/31218/How-do-I-configure-my-Orbi-router-to-act-as-an-access-point and https://www.youtube.com/watch?v=H7LOcJ8GdDo&app=desktop

Try option #2 first...

[FURRYe38]

What Firmware version is currently loaded?
What is the Mfr and model# of the Internet Service Providers modem/ONT the NG router is connected too?

Does Tunnelbrick support have any information regarding this? 

[CrimpOn]

OpenVPN on a home router is intended to allow the owner to access devices on the local networkk when away. i.e. to get "into" the router from the internet. 

Accessing a company VPN is entirely different and may require specific VPN software and security certificates.  The company IT department should be able to provide that information.

[basic]

What Firmware version is currently loaded?

V2.7.3.22

What is the Mfr and model# of the Internet Service Providers modem/ONT the NG router is connected too?

Arris BGW320-505 AT&T

Does Tunnelbrick support have any information regarding this?

I hadn't checked. I assumed that it had something to do with the nonwindows VPN configuration with the Orbi router. When connected to the modem I'm able to use the other VPN configurations without a problem.

[basic]

The problem is that the Orbi is blocking use of any VPN and the setup instructions (https://kb.netgear.com/25389/Enabling-VPN-service-on-a-NETGEAR-router-using-a-MAC-OS-computer) have led me to this point. I'm able to use the company VPN when I'm wired in to the modem with Tunnelbrick just fine.

[FURRYe38 · Accepted solution]

Your ISP Modem already has a built in router and wifi. This would be a double NAT (two router) condition which isn't recommended. https://kb.netgear.com/30186/What-is-Double-NAT
https://kb.netgear.com/30187/How-to-fix-issues-with-Double-NAT
Couple of options,
1. Configure the modem for transparent bridge or modem only mode. Then use the Orbi router in router mode. You'll need to contact the ISP for help and information in regards to the modem being bridged correctly.
2. If you can't bridge the modem, disable ALL wifi radios on the modem, configure the modems DMZ/ExposedHost or IP Pass-Through for the IP address the Orbi router gets from the modem. Then you can use the Orbi router in Router mode.
3. Or disable all wifi radios on the modem and connect the Orbi router to the modem, configure AP mode on the Orbi router. https://kb.netgear.com/31218/How-do-I-configure-my-Orbi-router-to-act-as-an-access-point and https://www.youtube.com/watch?v=H7LOcJ8GdDo&app=desktop

Try option #2 first...