VPN Connection Problem

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Hi,
I’m using OpenVPN client for mac and I configured everything and I’m able to connect to the server and everything but I can’t use my VPN IP!

I’m at 10.10.*.* and when I try to connect to myself from the localhost I don’t get the connection, so I’m not able to make a reverse shell…

The VPN is at “utun2” and here is the ifconfig for it

utun2: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1500
	inet 10.10.14.31 --> 10.10.14.1 netmask 0xfffffe00 
	inet6 fe80::aede:48ff:fe00:1122%utun2 prefixlen 64 scopeid 0x19 
	inet6 dead:beef:2::101d prefixlen 64 
	nd6 options=201<PERFORMNUD,DAD>

There is this POINTOPOINT thing that when I googled I found this thread networking - What does it mean 10.171.10.1 --> 10.171.10.2 in openvpn-created interface? - Unix & Linux Stack Exchange

I’m not really familiar with this level of networking so if someone is please share how can I solve it?

I believe I need to write something on the ovpn file to change the setting of this configuration…

last this is my ping inside 10.10.*.* if is wasn’t working I’ll get this strange error

xhzeem@local:~$ ping 10.10.14.10

92 bytes from 10.10.14.1: Destination Host Unreachable
Vr HL TOS  Len   ID Flg  off TTL Pro  cks      Src      Dst
 4  5  00 5400 e145   0 0000  3f  01 6e27 10.10.14.10  10.10.10.10 

Thanks.

I dont know enough about how VPNs work on a mac to be much help.

However if you go to Login :: Hack The Box :: Penetration Testing Labs you can verify if you have access by checking “HTB Lab Access Details”

Type your comment> @TazWake said:

I dont know enough about how VPNs work on a mac to be much help.

However if you go to Login :: Hack The Box :: Penetration Testing Labs you can verify if you have access by checking “HTB Lab Access Details”

I have a working connection and I can access the machines but it’s configured in a wired way…

@xhzeem said:

I have a working connection and I can access the machines but it’s configured in a wired way…

Macs are strange beasts.

Hi,
i have same problem like you on my mac. did you already solved this problem ?
Thanks ^^

Started encountering the same issue a few days ago, after probably 6+ months of a working setup (OS X & brew-installed openvpn). After significant debugging, I believe it’s something to do with the routing that gets applied to vpn (utun*) interfaces. I don’t know exactly how to solve it, so like others in this post I’m swapping to using VM-based attack boxes from now (which is probably what I should have always been using, anyway).

It is a very strange error indeed. I use macOS 12 Monterey and I faced a similar issue. In my case, whenever I connect to the VPN using OpenVPN, I am able to ping the server but loose access to every other thing on the internet outside the private network.

I solved this by renewing DHCP lease following these steps:

  1. Go to System Preferences → Go to Network
  2. In Network, click Advanced on the bottom right
  3. Click on TCP/IP tab
  4. Click Renew DHCP Lease button. Click Ok…then click Apply to apply the settings.

From here on, I have access to the internet and things work as they should. Unfortunately I have to do this everytime I open a VPN connection to HTB.