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,A1) Benefits of pentesting Manage risk. Increase business continuity. Minimise client-side attacks. Protect
clients, partners and third-parties. Comply with regulation.
A1) Pentest structure Reconnaissance (i.e. find live hosts, sweeping, find services, scanning, banner
matching, find vulnerabilities). Target prioritisation (e.g. assess servers rather
than printers). Testing of services and exploitation if applicable. Consult/Confirm
with customer if ok to exploit. Inform customer of any high risk issues that need
addressing immediately.
A1) Project Lifecycle Data Gathering / Scoping / Briefing. Testing. Report Writing. Debriefing
A2) Computer Misuse Act 1990 The Act defines 3 specific offences: 1. Unauthorised access to computer material
(that is, a program or data). 6 months or Level 5 fine (£5000 currently). 2.
Unauthorised access to a computer system with intent to commit or facilitate the
commission of a serious crime. 5 years, max fine. 3. Unauthorised modification
of computer material. 5 years, max fine. In general: You must not test a system
without prior authorisation (e.g. as agreed in written scope/contract). You should
never test without informing the client beforehand. Amended by Part 5 of Police
and Justice Act 2006.
A2) Police and Justice Act 2006 An amendment and update to the Computer Misuse Act 1990 in Part 5 of the
Police and Justice Act 2006 are: Section 35. Unauthorised access to computer
material. Section 36. Unauthorised acts with intent to impair operation of
computer, etc. Section 37. Making, supplying or obtaining articles for use in
computer misuse offences. Section 38. Transitional and saving provision. In
general: Part V includes a few sections on Computer Misuse Act 1990. Provision
for DoS as an offence. Increased penalties. Making available tools to the
Internet. Dual-use tools liable.
A2) Human Rights Act 1998 Lots of general human rights involved such as right to marry, discrimination,
privacy, slavery, guilty etc. Human Rights Act 1998 is relevant to Computer usage
as: "Protects the right of individuals against unreasonable disruption of and
intrusion into their lives, while balancing this individual right with those of others."
In general: Article 8: Right to respect for private and family life. Right to privacy.
With Acceptable Usage Policy (AUP), you waive the right to privacy on network.
A2) Data Protection Act 1998 In general: Deals with PII (Personal Information ID). Data about identifiable users
should only be used for the purpose intended. Should not make a local copy (e.g.
HR Database)
A2) Handling Data (6 catergories) Data classification set by uk.gov. Important for CHECK member to know the
protective marking of test/report. 1. NPM — Non Protective Marking. 2.
PROTECT — Not sensitive enough to make classification. Sensitive but not high
risk. 3. RESTRICTED — Pentests are usually RESTRICTED as a minimum 4.
CONFIDENTIAL — (Prejudical). 5. SECRET — (Serious Injuries). 6. TOP
SECRET (EGD).
A4) 5 Principles of Risk Management Assess risk and determine needs. Establish a central management focus.
Implement appropriate policies and related controls. Promote awareness.
Monitor and evaluate policy and control effectiveness.
A3) Sensible scoping questions (7) 1. What technologies are being used? 2. Can we get access to the application
(Web Application)? 3. How many users are there? 4. How many pages are
there? Are they dynamic or static? 5. What are you expecting us to find? 6. Will
this be a white box or black box test? 7. Will the testing be onsite or remote?
B1) OSI Open Standards Interconnection (OSI) developped by International Standards
Organisation (ISO)
B1) OSI Model. What and stages? Model is set of 7 layers that define the different stages that data must go through
to travel from one device to another over a network. {7} Application, {6}
Presentation, {5} Session, {4} Transport, {3} Network, {2} Data Link, {1} Physical.
Higher layers more specific, lower layers more generic. Please Do Not Tell Sales
People Anything.
,B1) Physical Layer Physical layer defines electrical and physical specifications for devices, i.e.
relationship between a device and a transmission medium (e.g. copper or fibre
optical cable, Shielded/unshielded twisted pair, 10Base-2, 10Base-T, 100Base-
TX, 1000B-T, RJ45, Coaxial, Fibre-optical cables, Copper cables)
B1) Data Link Layer Data Link layer provides means to transfer data between network entities using a
common addressing format. Data Link layer has Logical Link Control (LLC)
sublayer for multiplexing several network protocols (e.g. IP, IPX, Decnet and
Appletalk) to coexist in multipoint network. Data Link layer has Media Access
Control (MAC) sublayer for addressing and terminal/network nodes to
communicate within a multiple access network. MAC address, PPP, HDLC,
ADCCP.
B1) Network Layer Network layer provides means of transferring data from a source host on one
network to a destination host on a different network. IP Address, ARP, IPv4, IPv6,
ICMP, IPX, RIP, IKE.
B1) Transport Layer Transport layer provides transparent transfer of data using connection-oriented
data stream support, reliability, flow control, and multiplexing. Port Number, TCP,
UDP, SCTP.
B1) Session Layer Session layer provides mechanism for opening, closing and managing a session
between end-user application processes, i.e., a semi-permanent dialogue.
SOCKS, TLS-PSK, TLS-SRP.
B1) Presentation Layer Presentation layer is responsible for the delivery and formatting of information to
the application layer for further processing or display. MIME, Netware Core
Protocol, XML.
B1) Application Layer Application layer is outermost layer where user interact directly with the software
application. FTP, SSH, Telnet, SMTP, IMAP, POP, HTTP, HTTPS, RTP, BOOTP,
SNMP, NTP.
B1) TCP/IP Model Layers TCP/IP model is basically a shorter version of the OSI model. Consists of four
instead of seven layers. Application, Transport, Network and Link. TCP
Application layer is like Application, Presentation and Session of OSI. TCP
Transport aka 'Host-to-host transport' is Transport in OSI. TCP Network aka
'Internet Layer' is Network OSI. TCP Link aka 'Network Access' is Data Link and
Physical OSI.
B1) TCP/IP Transport and Application Layer Transport Layer is a convenient application programming interface to internet
hosts. Application Layer contains all protocols and methods that fall into the
realm of process-to-process communications across an IP network.
B1) IPv4 IPv4 uses a 32-bit address for its Internet addresses. That means it can provide
support for 2^32 IP addresses in total â around 4.29 billion
B1) IPv6 Size and Advantages IPv6 utilizes 128-bit Internet addresses. No more NAT. No more private address
collisions. More efficient, many other benefits. Leading zeros can be omitted. The
double colon (::) can be used once in the text form of an address, to designate
any number of 0 bits.
B1) TCP Characteristics (3) 1) Transmission Control Protocol/Internet Protocol. 2) It is specifically designed
as a model to offer highly reliable and end-to-end byte stream over an unreliable
network. 3) A TCP connection is established with the help of three-way
handshake. It is a process of initiating and acknowledging a connection. Once
the connection is established, data transfer begins, and when the transmission
process is finished, the connection is terminated by the closing of an established
virtual circuit. The connection is full duplex, and both sides synchronize (SYN)
and acknowledge (ACK) each other. The exchange of these four flags is
performed in three steps—SYN, SYN-ACK, and ACK
B1) UDP Characteristics 1) User Datagram Protocol (A datagram is a transfer unit associated with a
packet-switched network.) 2) Datagram oriented protocol. It is used for broadcast
and multicast type of network transmission. 3) The UDP protocol works almost
similar to TCP, but it throws all the error-checking stuff out, all the back-and-forth
communication and deliverability. UDP uses a simple transmission method
without implied hand-shaking dialogues for ordering, reliability, or data integrity.
, B1) TCP vs UDP (6) 1) TCP is a connection-oriented protocol, whereas UDP is a connectionless
protocol. 2) The speed for TCP is slower while the speed of UDP is faster. 3)
TCP uses handshake protocol like SYN, SYN-ACK, ACK while UDP uses no
handshake protocols. 4) TCP does error checking and also makes error
recovery, on the other hand, UDP performs error checking, but it discards
erroneous packets. 5) TCP has acknowledgment segments, but UDP does not
have any acknowledgment segment. 6) TCP is heavy-weight, and UDP is
lightweight.
B1) ICMP 1) The Internet Control Message Protocol (ICMP) is a network layer protocol
used by network devices to diagnose network communication issues. 2) The
primary purpose of ICMP is for error reporting. ICMP is mainly used to determine
whether or not data is reaching its intended destination in a timely manner. 3)
Unlike the Internet Protocol (IP), ICMP is not associated with a transport layer
protocol such as TCP or UDP. This makes ICMP a connectionless protocol: one
device does not need to open a connection with another device before sending
an ICMP message. Normal IP traffic is sent using TCP, which means any two
devices that exchange data will first carry out a TCP handshake to ensure both
devices are ready to receive data. ICMP does not open a connection in this way.
The ICMP protocol also does not allow for targeting a specific port on a device.
B1) ICMP Probing/Ping sweep Type 8 (Echo Request) - used to perform ping sweeping in order to determine
whether hosts are accessible: root@kali:~# ping 192.168.51.29. Can use Nmap
to perform ping sweep across a whole network IP range: nmap -sP
192.168.51.0/24
B1) ICMP Types Type 8 (echo request) = Ping packets. Type 13 (timestamp request) = Used to
obtain system time from the target host. Type 15 (information request) = Rarely
used, intended to support self-configuring systems to allow then to discover their
network addresses. Type 17 (subnet address mask request) = Reveals the
subnet mask used by the target host, used when mapping networks
B1) ICMP Probing tools Sing (works like Ping but with enhancements as you can send diff types of
ICMP). Works like "sing -echo" "sing -tstamp" "sing -mask". nmap -sP.
ICMPscan, can do all of the ICMP types with flags -T (timestamp) -N (Netmask) -
I (info) -E (echo)
B1) ICMP OS Fingerprinting Ofir Arkin's Xprobe2 utility performs OS fingerprinting by primarily analyzing
responses to ICMP probes
B1) Microsoft PPTP 1. The Point-to-Point Tunneling Protocol (PPTP) is an obsolete method for
implementing virtual private networks. A PPTP tunnel is started by
communication to the peer on TCP port 1723. This TCP connection is then used
to initiate and manage a GRE tunnel to the same peer. Generic Routing
Encapsulation (GRE) is a tunneling protocol developed by Cisco Systems that
can encapsulate a wide variety of network layer protocols inside virtual point-to-
point links or point-to-multipoint links over an Internet Protocol network. Microsoft
PPTP uses TCP port 1723 to negotiate and establish connection and IP protocol
47 (GRE) for data communication. 2. Uses MS-CHAP for authentication which
PPTPv1 and PPTPv2 and vulnerable to bruteforce attacks.
B2) Cat 5/Fibre Coaxial/Cat 5/Fiber Optics is pyhsical part of the physical layer. Coax cable is an
older technology used in connecting networks. Cat 5 is made from copper and is
twister pairs.
B2) Cat 5 Characteristics 1) Performance up to 100MHz 2) Suitable for 10BASE-T, 100BASE-TX (Fast
Ethernet), 1000BASE-T (Gigabit Ethernet). 3) Category 5 enhanced (Cat 5e)
supersedes Cat 5. Category 6 cable (Cat 6) is a cable standard for Gigabit
Ethernet. 4) Normally use RJ45 connectors.
B2) What are 10/100/1000baseT (Ethernet) 1) They are standards that carry traffic on physical layers.
B2) 10base T characteristics - 1) Also known as ethernet over twisted pair or IEEE 802.3i
2)10base-T transmits at speed of 10Mbit/s using baseband transmission using
twisted pair cables