AR300M Double VPN - Works off Cell Phone but Not at Hotel

Technical Support for Routers
1

AR300M has OpenVPN client running and connected to my home router which has OpenVPS server running, VPN connection between the AR300M and my home router is working (except under one scenario).
Scenario 1 -
AR300M connected bridge mode to Hotel’s WiFi, VPN enabled.
Work laptop (software VPN disabled), and mobile devices connect and have internet, everything works fine.

Scenario 2 -
AR300M connected bridge mode to my cell phone’s WiFi sharing, VPN enabled.
Work laptop (software VPN disabled),and mobile devices connect and have internet, everything works fine.

Scenario 3 - (same as scenario 1 but I ENABLE software VPN on work laptop)
AR300M connected bridge mode to Hotel’s WiFi, VPN enabled.
Work laptop (software VPN ENABLED), and mobile devices unable to get internet anymore. I can still access the router admin page and my home network router settings page, but I have no internet. I have to turn off the software VPN on my work laptop and restart the AR300M and have everything as scenario 1 for everything to work again.

Scenario 4 - (same as scenario 2 but I ENABLE software VPN on work laptop)
AR300M connected bridge mode to my cell phone’s WiFi sharing, VPN enabled.
Work laptop (software VPN ENABLED),and mobile devices connect and have internet, everything works fine.

 
Does anyone have any idea what could potentially be causing the AR300M to stop allowing internet/partially crashing when I enable my laptops software VPN as well. It only does it while the ARM300M is connected to the hotel’s WiFi. The AR300M does fine when connected to my cell phone’s WiFi sharing.

2

Does the hotel wifi has a captive portal that need to be authenticated?

If you enable vpn, then the portal is not accessible. So you have to disable vpn and get through the portal.

3

Yes the hotel has a captive portal. But the problem happens when I enable the software VPN on my laptop, not the AR300M.

If you read in scenario 1, everything works fine with the router connected to the Hotel’s WiFi with the VPN turned on in the AR300M. The problem occurs when I turn on a separate VPN on the laptop itself. When that happens the router stops allowing internet, the laptops own VPN needs to be turned off and the router rebooted in order to work again. The captive portal has already been cleared, so its not that.

I don’t get the same problem if the AR300M is connected to my cell phone’s wifi.

4

Can you please check the IP address of both your vpn?

The mini router’s VPN IP address should not in the same subnet as your laptop’s vpn IP address. Both of them cannot be in the same subnet as the hotel’s IP address.

5

AR300M Repeater Connection to Hotel WiFI
IPAddr 172.16.0.213
Netmask 255.255.248.0

Personal Laptop (no software VPN) - connected to AR300M
IPv4 Adddress 192.168.8.141
IPv4 Subnet Mask 255.255.255.48

Work Laptop (software VPN ON) - connected to AR300M
192.168.8.202
IPv4 Subnet Mask 255.255.255.0
It’s VPN Connection
172.19.224.139

 

 

I am leaving the hotel today, so not much of a big deal now. But would like to prevent this in the future