Having trouble connecting via OpenVPN through Kali Linux

Off-topic
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1

Hi, I’m unable to connect to the Starting Point (or any lab) server through OpenVPN. I’m using Kali Linux on ChromeOS. I’ve tried researching and switching files and a few other things I’ve come across, but none are working.

Here is my log:

2022-11-06 03:35:12 WARNING: Compression for receiving enabled. Compression has been used in the past to break encryption. Sent packets are not compressed unless “allow-compression yes” is also set.
2022-11-06 03:35:12 OpenVPN 2.5.7 x86_64-pc-linux-gnu [SSL (OpenSSL)] [LZO] [LZ4] [EPOLL] [PKCS11] [MH/PKTINFO] [AEAD] built on Jul 5 2022
2022-11-06 03:35:12 library versions: OpenSSL 3.0.7 1 Nov 2022, LZO 2.10
2022-11-06 03:35:12 Outgoing Control Channel Encryption: Cipher ‘AES-256-CTR’ initialized with 256 bit key
2022-11-06 03:35:12 Outgoing Control Channel Encryption: Using 256 bit message hash ‘SHA256’ for HMAC authentication
2022-11-06 03:35:12 Incoming Control Channel Encryption: Cipher ‘AES-256-CTR’ initialized with 256 bit key
2022-11-06 03:35:12 Incoming Control Channel Encryption: Using 256 bit message hash ‘SHA256’ for HMAC authentication
2022-11-06 03:35:12 TCP/UDP: Preserving recently used remote address: [AF_INET]23.19.62.79:443
2022-11-06 03:35:12 Socket Buffers: R=[87380->87380] S=[16384->16384]
2022-11-06 03:35:12 Attempting to establish TCP connection with [AF_INET]23.19.62.79:443 [nonblock]
2022-11-06 03:35:13 TCP connection established with [AF_INET]23.19.62.79:443
2022-11-06 03:35:13 TCP_CLIENT link local: (not bound)
2022-11-06 03:35:13 TCP_CLIENT link remote: [AF_INET]23.19.62.79:443
2022-11-06 03:35:13 TLS: Initial packet from [AF_INET]23.19.62.79:443, sid=cd1f29dd 48857f65
2022-11-06 03:35:14 VERIFY OK: depth=1, CN=HackTheBox
2022-11-06 03:35:14 VERIFY KU OK
2022-11-06 03:35:14 Validating certificate extended key usage
2022-11-06 03:35:14 ++ Certificate has EKU (str) TLS Web Server Authentication, expects TLS Web Server Authentication
2022-11-06 03:35:14 VERIFY EKU OK
2022-11-06 03:35:14 VERIFY OK: depth=0, CN=htb
2022-11-06 03:35:15 Control Channel: TLSv1.3, cipher TLSv1.3 TLS_AES_256_GCM_SHA384, peer certificate: 2048 bit RSA, signature: RSA-SHA256
2022-11-06 03:35:15 [htb] Peer Connection Initiated with [AF_INET]23.19.62.79:443
2022-11-06 03:35:15 PUSH: Received control message: ‘PUSH_REPLY,route 10.10.10.0 255.255.254.0,route 10.129.0.0 255.255.0.0,route-ipv6 dead:beef::/64,tun-ipv6,route-gateway 10.10.16.1,topology subnet,ping 10,ping-restart 120,ifconfig-ipv6 dead:beef:4::10ca/64 dead:beef:4::1,ifconfig 10.10.16.204 255.255.254.0,peer-id 0,cipher AES-256-CBC’
2022-11-06 03:35:15 OPTIONS IMPORT: timers and/or timeouts modified
2022-11-06 03:35:15 OPTIONS IMPORT: --ifconfig/up options modified
2022-11-06 03:35:15 OPTIONS IMPORT: route options modified
2022-11-06 03:35:15 OPTIONS IMPORT: route-related options modified
2022-11-06 03:35:15 OPTIONS IMPORT: peer-id set
2022-11-06 03:35:15 OPTIONS IMPORT: adjusting link_mtu to 1627
2022-11-06 03:35:15 OPTIONS IMPORT: data channel crypto options modified
2022-11-06 03:35:15 Data Channel: using negotiated cipher ‘AES-256-CBC’
2022-11-06 03:35:15 Outgoing Data Channel: Cipher ‘AES-256-CBC’ initialized with 256 bit key
2022-11-06 03:35:15 Outgoing Data Channel: Using 256 bit message hash ‘SHA256’ for HMAC authentication
2022-11-06 03:35:15 Incoming Data Channel: Cipher ‘AES-256-CBC’ initialized with 256 bit key
2022-11-06 03:35:15 Incoming Data Channel: Using 256 bit message hash ‘SHA256’ for HMAC authentication
2022-11-06 03:35:15 net_route_v4_best_gw query: dst 0.0.0.0
2022-11-06 03:35:15 net_route_v4_best_gw result: via 0.0.0.0 dev
2022-11-06 03:35:15 ROUTE_GATEWAY 0.0.0.0
2022-11-06 03:35:15 GDG6: remote_host_ipv6=n/a
2022-11-06 03:35:15 net_route_v6_best_gw query: dst ::
2022-11-06 03:35:15 sitnl_send: rtnl: generic error (-101): Network is unreachable
2022-11-06 03:35:15 ROUTE6: default_gateway=UNDEF
2022-11-06 03:35:15 TUN/TAP device tun0 opened
2022-11-06 03:35:15 net_iface_mtu_set: rtnl: cannot get ifindex for tun0: No such device (errno=19)
2022-11-06 03:35:15 Linux can’t set mtu (1500) on tun0
2022-11-06 03:35:15 Exiting due to fatal error

Can anyone help me figure out what the issue is?

2

Hello.
Kali is deployed as a virtual machine or as a standalone operating system. ?
If you’ve deployed Kali on a Windows virtual machine, then the first thing to do is turn off the Windows firewall and you should be up and running.
If you have Kali Linux deployed as your main operating system, then look at the network interface settings, most likely you did not correctly import the settings of the open vpn configuration file.
You do not have completed ip addresses.
2022-11-06 03:35:15 net_route_v4_best_gw request: dst 0.0.0.0
2022-11-06 03:35:15 net_route_v4_best_gw result: via 0.0.0.0 dev
2022-11-06 03:35:15 ROUTE_GATEWAY 0.0.0.0
Please see this link, I wrote how to import config file in Kali. php-reverse-shell.php issue - #29 by XANTAN
Good luck.

3

Thank you for your reply and insight. I’m running my Kali through Crouton on my Chromebook. It’s basically a virtual machine instance. I will look into your post when I get the chance to see if that gets me to the right place.

4

As the default Kali user, be sure to sudo.
sudo openvpn bla.ovpn