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Trouble setting up OpenVPN server + Tunnelblick on Mac

ionblue

Occasional Visitor
I'm trying to setup OpenVPN server on my AC5300 (v. 380.67) and for the life of me I can't get the client, Tunnelblick on Mac, to connect. Admittedly, I have no idea what I'm doing with the settings in either place, but I've tried a ton of different configurations and none will connect. I'm also not seeing any errors on the client side or on the router so I'm at a loss as to where to start troubleshooting.

As a last ditch effort I reset to defaults, didn't change anything, exported the file, imported the file on the client and when I try to connect it just says "waiting for connection". Then does nothing till I cancel.

Could someone help me with at least a starting point? Looking at the documentation is getting me nowhere I'm afraid.
 

ionblue

Occasional Visitor
The only thing I see on the router side is this when OpenVPN starts up:

Could not determine IPv4/IPv6 protocol. Using AF_INET6

Does that mean it's trying to use IPv6? I don't have that enabled.
 

RMerlin

Asuswrt-Merlin dev
Make sure you get the Tunnelblick version that's based on OpenVPN 2.4 and not 2.3. Also test from outside your network (i.e. over LTE or from outside home).
 

ionblue

Occasional Visitor
Make sure you get the Tunnelblick version that's based on OpenVPN 2.4 and not 2.3. Also test from outside your network (i.e. over LTE or from outside home).
The one I downloaded has 2.4.3 support, but I'll double check it. I did try using an LTE connection to come in from the outside, however I didn't try that after I reset it. I'll try it as is though.


Sent from my iPad using Tapatalk
 

RMerlin

Asuswrt-Merlin dev
If it doesn't even connect at all, then most likely reasons:

- Your router is behind another firewall
- You're using the wrong port or protocol (unlikely if you imported the ovpn)
- You're connecting to the wrong address
- Either your mobile provider or your ISP is blocking the port/protocol you are trying to use (some mobile providers will do that)
 

ionblue

Occasional Visitor
If it doesn't even connect at all, then most likely reasons:

- Your router is behind another firewall
- You're using the wrong port or protocol (unlikely if you imported the ovpn)
- You're connecting to the wrong address
- Either your mobile provider or your ISP is blocking the port/protocol you are trying to use (some mobile providers will do that)
Well, I now see that the IP that is getting resolved from the ASUS dynamic DNS is not correct. That will obviously be a problem. I tried disabling then enabling that service again to update the IP, but it did not. Any way to force an update?
 

RMerlin

Asuswrt-Merlin dev
Well, I now see that the IP that is getting resolved from the ASUS dynamic DNS is not correct. That will obviously be a problem. I tried disabling then enabling that service again to update the IP, but it did not. Any way to force an update?
The IP should update whenever the WAN IP changes. You could try rebooting the router to force a refresh, but if the IP isn't correct, it might indicate a problem with your Asus DDNS account.

Personally, I recommend looking at a different dyndns service. Asus's service has had a couple of extended outages over the years.
 

ionblue

Occasional Visitor
The IP should update whenever the WAN IP changes. You could try rebooting the router to force a refresh, but if the IP isn't correct, it might indicate a problem with your Asus DDNS account.

Personally, I recommend looking at a different dyndns service. Asus's service has had a couple of extended outages over the years.
Thanks. I got a DynDNS account and I can now connect. I did get a pop-up saying that my local IP didn't change, but I didn't dig any further. When I check it in my phone I am seeing a different IP so I'm not sure if there's an issue or not. I'll check it again shortly to make sure it's operating as it should on the Mac side.
 

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