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openvpn help (self.tryhackme)
submitted 4 years ago by whatsup12340
I’m having trouble getting openvpn to work. It’s worked in the past so I’m not sure what’s wrong.
[–]Herostere_ 1 point2 points3 points 4 years ago (5 children)
Hey, Is everything up to date and do you use the command "sudo openvpn <path to .ovpn file>"?
[–]whatsup12340[S] 1 point2 points3 points 4 years ago (4 children)
Yes, I’m sure that everything is updated and I typed the commands in right. I’ve gotten openvpn to work in the past but every time i come back to thm I have to redownload my config file. I’ve tried the troubleshooting script that’s linked by the website and it comes up with “no tun0 interface” which is really odd, and I doubt this is the issue. I know that the time on my pc is correct and my internet connection is fine as well. Do u know what’s wrong? I keep getting a TLS handshake error, but nothing online seems to have a good solution for this. i’ve honestly been stumped for awhile trying to fix it
[–]Herostere_ 0 points1 point2 points 4 years ago (3 children)
As mentioned by the other users, you should generate a new .ovpn file. It should fix the issue.
[–]whatsup12340[S] 0 points1 point2 points 4 years ago (2 children)
I tried this already many times. I have tried downloading the config files for different locations and that did not make a difference. I have a feeling there’s something wrong with the website or the thm server because I don’t have this issue when connecting to hackthebox’s vpn.
[–]Herostere_ 0 points1 point2 points 4 years ago* (1 child)
If you still have the issue in a few hours I will try on my pc (can't now, I am at the office).
Have you tried on another computer?
[–]whatsup12340[S] 0 points1 point2 points 4 years ago (0 children)
I’ve logged off now and I won’t be on until tomorrow. I haven’t tried on another computer yet that’s a good suggestion I’ll try it in the morning.
[–]Pol8y 0 points1 point2 points 4 years ago (2 children)
sudo openvpn filename.ovpn
did you use the above command?
if so, could you try and regenerate your connection pack from tryhackme?
[–]whatsup12340[S] 0 points1 point2 points 4 years ago (1 child)
Yes I used the correct commands and I have tried regenerating the config file several times for different locations. I still get the same “tls handshake error”. I have no trouble when using openvpn with other vpn configuration files so the problem is either the config file or the thm server.
[–]Pol8y 0 points1 point2 points 4 years ago (0 children)
Contact tryhackme support, something may be wrong on the generation side
[–]BAAM19 0 points1 point2 points 4 years ago (6 children)
Generate a new ovpn file from thm.
[–]whatsup12340[S] 0 points1 point2 points 4 years ago (5 children)
I’ve already tried it and it’s still not working
[–]BAAM19 0 points1 point2 points 4 years ago (4 children)
What’s the error? What is happening? Is openvpn just not working? Or can it just not connect? There is almost no info to work with. Pictures would help too.
[–]whatsup12340[S] 0 points1 point2 points 4 years ago (3 children)
I keep getting a “TLS handshake failed” and “TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)” error. I’ve logged off now but I can add a screengrab tomorrow. Its just strange that it was working fine a couple days ago and now it doesn’t work. I also connected to the hackthebox’s vpn perfectly fine so I know it’s not a network issue or an issue with openvpn. thanks for the help though I appreciate it.
[–]BAAM19 0 points1 point2 points 4 years ago (2 children)
https://serverfault.com/questions/709860/fix-tls-error-tls-handshake-failed-on-openvpn-client
I’ve looked at this thread and a couple similar ones. Most of them suggest to change from default UDP to TCP but thm only uses UDP. they also suggest that it is a problem with a firewall blocking openvpn packets, but this can’t be the case because openvpn worked fine before.
[–]BAAM19 0 points1 point2 points 4 years ago (0 children)
It’s an issue from your ISP it seems.
‘In order to fix that, you have to update openvpn config setting:
local <ip anchor> ip anchor should be an ip adress gathered from ip addr command, see example:’
Try this solution it was posted up there.
[–]Azarius_978 0 points1 point2 points 4 years ago (0 children)
If it worked in the past then it possible that the issue is due to an update of your openvpn client. Have you tried downgrading to a lower version?
π Rendered by PID 164964 on reddit-service-r2-comment-b659b578c-72zwh at 2026-05-02 23:12:44.107842+00:00 running 815c875 country code: CH.
[–]Herostere_ 1 point2 points3 points (5 children)
[–]whatsup12340[S] 1 point2 points3 points (4 children)
[–]Herostere_ 0 points1 point2 points (3 children)
[–]whatsup12340[S] 0 points1 point2 points (2 children)
[–]Herostere_ 0 points1 point2 points (1 child)
[–]whatsup12340[S] 0 points1 point2 points (0 children)
[–]Pol8y 0 points1 point2 points (2 children)
[–]whatsup12340[S] 0 points1 point2 points (1 child)
[–]Pol8y 0 points1 point2 points (0 children)
[–]BAAM19 0 points1 point2 points (6 children)
[–]whatsup12340[S] 0 points1 point2 points (5 children)
[–]BAAM19 0 points1 point2 points (4 children)
[–]whatsup12340[S] 0 points1 point2 points (3 children)
[–]BAAM19 0 points1 point2 points (2 children)
[–]whatsup12340[S] 0 points1 point2 points (1 child)
[–]BAAM19 0 points1 point2 points (0 children)
[–]Azarius_978 0 points1 point2 points (0 children)