Penetration Testing with Kali Linux OffSec

sudo openvpn pen200.ovpn
2021-06-28 10:20:12 Note: Treating option '--ncp-ciphers' as '--data-ciphers' 
(renamed in OpenVPN 2.5). 
2021-06-28 10:20:12 DEPRECATED OPTION: --cipher set to 'AES-128-CBC' but missing in --
data-ciphers (AES-128-GCM). Future OpenVPN version will ignore --cipher for cipher 
negotiations. Add 'AES-128-CBC' to --data-ciphers or change --cipher 'AES-128-CBC' to 
--data-ciphers-fallback 'AES-128-CBC' to silence this warning. 
2021-06-28 10:20:12 OpenVPN 2.5.1 x86_64-pc-linux-gnu [SSL (OpenSSL)] [LZO] [LZ4] 
[EPOLL] [PKCS11] [MH/PKTINFO] [AEAD] built on May 14 2021 
2021-06-28 10:20:12 library versions: OpenSSL 1.1.1k 25 Mar 2021, LZO 2.10 
2021-06-28 10:20:12 TCP/UDP: Preserving recently used remote address: 
[AF_INET]192.95.19.165:1194 
2021-06-28 10:20:12 UDP link local: (not bound) 
2021-06-28 10:20:12 UDP link remote: [AF_INET]192.95.19.165:1194 
2021-06-28 10:20:12 [offsec.com] Peer Connection Initiated with 
[AF_INET]192.95.19.165:1194 
2021-06-28 10:20:13 TUN/TAP device tun0 opened 
2021-06-28 10:20:13 net_iface_mtu_set: mtu 1500 for tun0 
2021-06-28 10:20:13 net_iface_up: set tun0 up 
2021-06-28 10:20:13 net_addr_v4_add: 192.168.49.115/24 dev tun0 
2021-06-28 10:20:13 WARNING: this configuration may cache passwords in memory -- use 
the auth-nocache option to prevent this 
2021-06-28 10:20:13 
Initialization Sequence Completed
Listing 9 - Connecting to the labs VPN 
The output of Listing 9 may seem intimidating at first. For now, simply note that the last line of 
the output reads “Initialization Sequence Completed”, indicating that we have connected 
successfully to the VPN. Make sure that you can find it on your own connection! 
We must leave this command prompt open. Closing it will disconnect the VPN connection.
We can open another terminal tab by clicking 
File
> 
New Tab
. 
Once we are connected to the PWK VPN, we will be provided with a TUN0 network interface, 
which we can view with the 
ip a
command. The address assigned to the TUN0 interface will be 
192.168.119.X
, where 
X
is some value between 1 and 255. Every time we reconnect to the VPN, 
we might get assigned a different value for 
X
. 
In addition, all lab machines within the PWK environment will have addresses that follow the 
format 
192.168.X.Y
, where 
X
is the same value as the third octet of our TUN0 address, and 
Y
is 
the specific octet associated with the machine. 
In the course material, we will be using different IP addresses for our TUN0 network interface as 
well as for the lab machines. Please make sure you are using the IP addresses assigned to you 
via TUN0 and via the OLP so that you can access the machines properly. 
Lab time starts when your course begins and is metered as continuous access. 

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Penetration Testing with Kali Linux
PWK - Copyright © 2023 OffSec Services Limited. All rights reserved. 
22 
If your lab time expires, or is about to expire, you can purchase a lab extension at any time. To 
purchase additional lab time, use the 
Extend
link available at top right corner of the OffSec 
Training Library. If you purchase a lab extension while your lab access is still active, you can 
continue to use the same VPN connectivity pack. If you purchase a lab extension after your 
existing lab access has ended, you will need to download a new VPN connectivity pack via the 
course lab page in the OffSec Learning Portal 
learners who have purchased a subscription will have access to the lab as long as the 
subscription is active. Your subscription will be automatically renewed, unless cancelled via the 
billing page. 
2.2
How to Approach the Course 
This Learning Unit covers the following Learning Objectives: 
•
Conceptualize a learning model based on increasing uncertainty 
•
Understand the different learning components included in PWK 
2.2.1
A Model of Increasing Uncertainty 
Penetration testing - and information security in general - is fundamentally about