Information Gathering

Information Gathering is the systematic process of collecting, analyzing, and cataloging data about a target system, network, or organization. This critical phase transforms raw data into actionable intelligence by uncovering the target's architecture, identifying potential vulnerabilities, and mapping security mechanisms. Whether conducting a penetration test, security assessment, or threat analysis, effective information gathering determines the success of subsequent operations by providing the strategic and technical context needed for informed decision-making.

The Information Gathering Process

Information gathering follows a structured methodology:

1. Define Scope: Establish clear boundaries for what information to collect

2. Collect Data: Use multiple techniques and tools to gather information

3. Validate Information: Verify accuracy through cross-referencing sources

4. Analyze Findings: Identify patterns, vulnerabilities, and opportunities

5. Document Results: Create organized reports for future reference

6. Continuous Monitoring: Update information as the target evolves

Types of Information to Gather

Network Infrastructure

• IP address ranges and CIDR blocks

• Domain names and subdomains

• DNS server configurations

• Network topology and routing

• Firewall and security device placement

• Content Delivery Networks (CDNs)

Systems and Services

• Operating systems and versions

• Running services and open ports

• Application versions and patch levels

• Web servers and frameworks

• Database systems

• API endpoints

Organizational Information

• Company structure and departments

• Employee names, roles, and contact information

• Email address formats

• Physical locations and office addresses

• Business partners and vendors

• Technology stack and tools in use

Security Posture

• Security products deployed (firewalls, IDS/IPS, antivirus)

• Authentication mechanisms

• Security policies and procedures

• Incident response capabilities

• Compliance requirements (PCI-DSS, HIPAA, GDPR)

NMAP (Network Mapper)

NMAP is the industry-standard open-source tool for network discovery and security auditing, created by Gordon "Fyodor" Lyon. Originally released in 1997, NMAP has evolved into the most comprehensive and flexible network scanning tool available, used by security professionals, system administrators, and penetration testers worldwide. Its versatility stems from its extensive scanning techniques, scriptable interface (NSE), and cross-platform compatibility.

Core Capabilities of NMAP

1. Host Discovery

Identify which systems are online and reachable on a network without performing port scans.

Techniques:

• Ping Scan: ICMP echo requests

• TCP SYN Discovery: Sends SYN packets to common ports

• TCP ACK Discovery: Uses ACK packets to bypass simple firewalls

• UDP Discovery: Sends UDP packets to detect hosts

• ARP Scan: Layer 2 discovery for local networks (most reliable for LAN)

Example:

# Basic ping scan (no port scan)
nmap -sn 192.168.1.0/24

# Disable ping, assume all hosts are up
nmap -Pn 192.168.1.10

# ARP scan for local network (requires root/admin)
nmap -PR 192.168.1.0/24

2. Port Scanning

Determine which ports are open, closed, or filtered on target systems.

Scan Types:

• TCP SYN Scan (-sS): Stealthy, doesn't complete TCP handshake (requires root)

• TCP Connect Scan (-sT): Completes full TCP connection (works without root)

• UDP Scan (-sU): Scans UDP ports (slower, often filtered)

• Comprehensive: -sS -sU scans both TCP and UDP

Port Specifications:

• Specific ports: -p 22,80,443

• Port ranges: -p 1-1000

• All ports: -p- (1-65535)

• Top ports: --top-ports 100

• Protocol-specific: -p T:80,443,U:53,161

3. Version Detection

Identify the specific application and version running on open ports by analyzing service responses and fingerprints.

Example:

# Service version detection
nmap -sV 192.168.1.10

# Aggressive version detection (more probes)
nmap -sV --version-intensity 9 192.168.1.10

# Light version detection (fewer probes)
nmap -sV --version-intensity 2 192.168.1.10

Sample Output:

PORT     STATE SERVICE VERSION
22/tcp   open  ssh     OpenSSH 8.2p1 Ubuntu 4ubuntu0.5
80/tcp   open  http    Apache httpd 2.4.41 ((Ubuntu))
3306/tcp open  mysql   MySQL 5.7.22-0ubuntu0.18.04.1

4. Operating System Detection

Determine the operating system and hardware characteristics through TCP/IP stack fingerprinting.

Example:

# OS detection (requires root)
nmap -O 192.168.1.10

# Aggressive OS detection with version scanning
nmap -A 192.168.1.10

# OS detection without port scan
nmap -O -Pn --osscan-guess 192.168.1.10

Essential NMAP Command Reference

Basic Scans

# Quick scan of most common 100 ports
nmap --top-ports 100 192.168.1.10

# Scan specific ports
nmap -p 80,443,8080 192.168.1.10

# Fast scan (T4 timing)
nmap -F -T4 192.168.1.10

# Comprehensive scan
nmap -p- -sV -sC -O 192.168.1.10

Timing Templates

NMAP offers timing templates (-T0 through -T5) to control scan speed:

• T0 (Paranoid): Extremely slow, IDS evasion (5 minutes between probes)

• T1 (Sneaky): Slow, IDS evasion (15 seconds between probes)

• T2 (Polite): Slows down to use less bandwidth

• T3 (Normal): Default timing

• T4 (Aggressive): Fast scan, assumes reliable network

• T5 (Insane): Very fast, may sacrifice accuracy

# Stealthy slow scan
nmap -sS -T1 192.168.1.10

# Fast aggressive scan
nmap -T4 192.168.1.0/24

Output Formats

# Normal output to file
nmap -oN scan_results.txt 192.168.1.10

# XML output (parseable)
nmap -oX scan_results.xml 192.168.1.10

# Grepable output
nmap -oG scan_results.gnmap 192.168.1.10

# All formats at once
nmap -oA scan_results 192.168.1.10

# Script kiddie output (just for fun)
nmap -oS scan_results.txt 192.168.1.10

Advanced Techniques

# Scan using decoy addresses (obfuscation)
nmap -D RND:10 192.168.1.10

# Fragment packets (IDS/firewall evasion)
nmap -f 192.168.1.10

# Spoof source port
nmap --source-port 53 192.168.1.10

# Scan through proxy
nmap --proxies http://proxy:8080 192.168.1.10

# IPv6 scanning
nmap -6 fe80::1

NMAP Scripting Engine (NSE)

NSE extends NMAP's capabilities with hundreds of scripts for vulnerability detection, exploitation, and advanced enumeration.

Script Categories

• auth: Authentication testing

• broadcast: Network discovery via broadcast

• brute: Brute force attacks

• default: Default safe scripts (-sC)

• discovery: Additional network discovery

• dos: Denial of service testing

• exploit: Exploitation attempts

• intrusive: May crash services

• malware: Malware detection

• safe: Won't affect target

• version: Enhanced version detection

• vuln: Vulnerability detection

Using NSE Scripts

# Run default safe scripts
nmap -sC 192.168.1.10

# Run specific script
nmap --script=http-title 192.168.1.10

# Run multiple scripts
nmap --script=http-enum,http-headers 192.168.1.10

# Run all scripts in category
nmap --script=vuln 192.168.1.10

# Run scripts with wildcards
nmap --script="http-*" 192.168.1.10

# Pass arguments to scripts
nmap --script=http-brute --script-args userdb=users.txt,passdb=pass.txt 192.168.1.10

Popular NSE Scripts

# HTTP enumeration
nmap --script=http-enum -p 80 192.168.1.10

# SMB vulnerability detection
nmap --script=smb-vuln-* -p 445 192.168.1.10

# SSL/TLS analysis
nmap --script=ssl-enum-ciphers -p 443 192.168.1.10

# DNS zone transfer attempt
nmap --script=dns-zone-transfer --script-args=dns-zone-transfer.domain=example.com -p 53 ns1.example.com

# Database detection and enumeration
nmap --script=mysql-info,mysql-databases -p 3306 192.168.1.10

Practical NMAP Workflow

Phase 1: Quick Discovery

# Find live hosts
nmap -sn 192.168.1.0/24 -oA discovery

# Extract live hosts
grep "Status: Up" discovery.gnmap | cut -d ' ' -f 2 > live_hosts.txt

Phase 2: Port Scanning

# Fast scan for open ports
nmap -iL live_hosts.txt -p- --open -T4 -oA all_ports

# Focus on specific hosts with many open ports
nmap -iL high_value_targets.txt -p- -T4 -oA detailed_ports

Phase 3: Service Enumeration

# Version detection on discovered ports
nmap -iL live_hosts.txt -sV -sC -O -oA service_scan

# Deep version scanning
nmap -p <discovered_ports> -sV --version-intensity 9 -oA deep_versions

Phase 4: Vulnerability Assessment

# Run vulnerability scripts
nmap -iL targets.txt --script=vuln -oA vuln_scan

# Target-specific vulnerability checks
nmap -p 445 --script=smb-vuln-ms17-010 192.168.1.10

Hands-on Exercise

Exercise 1: Network Discovery

1. Scan your local network to identify active hosts: nmap -sn 192.168.1.0/24

2. Compare results with ARP scan: sudo nmap -PR 192.168.1.0/24

3. Document: Which method found more hosts? Why might this be?

Exercise 2: Service Fingerprinting

1. Identify a test system (your own VM or authorized lab)

2. Run: nmap -p- -sV -sC <target>

3. Analyze output:

   • What services are running?

   • Are any versions outdated?

   • What do the NSE scripts reveal?

Exercise 3: Comparing Scan Types

1. Run TCP SYN scan: sudo nmap -sS <target>

2. Run TCP Connect scan: nmap -sT <target>

3. Run UDP scan: sudo nmap -sU --top-ports 20 <target>

4. Document: Compare speed, results, and system logs

Exercise 4: NSE Script Exploration

1. List available HTTP scripts: ls /usr/share/nmap/scripts/ | grep http

2. Read script documentation: nmap --script-help http-enum

3. Run against test web server: nmap --script=http-enum -p 80,443 <target>

4. Analyze discovered paths and directories

Interpreting NMAP Results

Port States

• open: Service is actively accepting connections

• closed: Port is accessible but no service listening

• filtered: Firewall/filter is blocking probe (inconclusive)

• unfiltered: Port is accessible but state undetermined

• open|filtered: Cannot determine if open or filtered (UDP scans)

• closed|filtered: Cannot determine if closed or filtered (rare)

Common Port Numbers

Port	Service	Description
21	FTP	File Transfer Protocol
22	SSH	Secure Shell
23	Telnet	Unencrypted remote access
25	SMTP	Email transmission
53	DNS	Domain Name System
80	HTTP	Web traffic
110	POP3	Email retrieval
143	IMAP	Email retrieval
443	HTTPS	Encrypted web traffic
445	SMB	Windows file sharing
3306	MySQL	MySQL database
3389	RDP	Remote Desktop Protocol
5432	PostgreSQL	PostgreSQL database
8080	HTTP-ALT	Alternative HTTP port

NMAP Best Practices

Performance Optimization

• Use -T4 for most scans on reliable networks

• Scan top ports first: --top-ports 1000

• Parallelize: Scan multiple targets simultaneously

• Exclude unresponsive hosts with initial ping scan

• Use --min-rate and --max-rate for rate control

Stealth and Evasion

• Use SYN scans (-sS) instead of connect scans

• Randomize scan order: --randomize-hosts

• Fragment packets: -f

• Slow timing: -T0 or -T1

• Spoof source: -S <spoofed_ip> -e <interface>

Legal and Ethical Considerations

• Always obtain written authorization before scanning

• Stay within defined scope (IP ranges, ports)

• Use appropriate timing to avoid DoS

• Document all scan activities with timestamps

• Respect bandwidth and system resources

Common Errors and Troubleshooting

"You requested a scan type which requires root privileges"

Cause: SYN scan, OS detection, or certain features require root Solution: Use sudo nmap or run as administrator

"Note: Host seems down"

Causes: Host is actually down, firewall blocking, ICMP disabled Solutions:

• Use -Pn to skip host discovery

• Try different discovery methods: -PS, -PA, -PU

• Check with ping and traceroute

Slow UDP Scans

Cause: UDP is connectionless, requires timeouts Solutions:

• Scan only essential UDP ports: --top-ports 20

• Increase parallelism: --min-parallelism 100

• Use faster timing: -T4

No Version Information Detected

Causes: Service on non-standard port, custom software Solutions:

• Increase version intensity: --version-intensity 9

• Try -A for aggressive detection

• Manual banner grabbing with Netcat

Enumeration

Enumeration is the aggressive phase of information gathering where you extract granular details from identified services and systems. Unlike reconnaissance, which casts a wide net, enumeration drills deep into specific targets to extract user accounts, shares, configurations, and other sensitive data. This phase bridges scanning and exploitation by providing the specific details needed to compromise systems.

The Enumeration Process

1. Identify service/protocol (from port scanning)

2. Query service for detailed information

3. Extract data systematically

4. Validate findings through cross-referencing

5. Document for exploitation phase

Enumeration Techniques by Service

NetBIOS/SMB Enumeration (Windows Networks)

Purpose: Extract Windows network information including shares, users, groups, and policies.

Ports: 137 (NetBIOS Name), 139 (NetBIOS Session), 445 (SMB)

Tools and Commands:

# Enum4linux - Comprehensive SMB enumeration
enum4linux -a 192.168.1.10

# Enum4linux with username/password
enum4linux -u admin -p password -a 192.168.1.10

# NBTscan - NetBIOS name scanning
nbtscan 192.168.1.0/24

# SMBClient - List shares
smbclient -L //192.168.1.10 -N

# SMBMap - Share enumeration
smbmap -H 192.168.1.10

# CrackMapExec - Multi-function SMB tool
crackmapexec smb 192.168.1.10 --shares

Information Extracted:

• Workgroup/domain name

• Operating system and version

• User accounts and groups

• Password policies

• Network shares and permissions

• Logged-in users

• RID cycling results

Example enum4linux Output Analysis:

[+] Got OS info for 192.168.1.10 from smbclient
[+] Got domain/workgroup name: WORKGROUP
[+] Password Info for Domain: WORKGROUP
    [+] Minimum password length: 7
    [+] Password history length: None
    [+] Maximum password age: 42 Days

[+] Users on 192.168.1.10
    user:[Administrator] rid:[0x1f4]
    user:[Guest] rid:[0x1f5]
    user:[john.doe] rid:[0x3e8]

SNMP Enumeration

Purpose: Extract device configurations, network topology, and system information from SNMP-enabled devices.

Port: 161 (UDP)

Tools and Commands:

# SNMPwalk - Walk entire MIB tree
snmpwalk -v 2c -c public 192.168.1.1

# Enumerate specific OIDs
snmpwalk -v 2c -c public 192.168.1.1 1.3.6.1.2.1.1  # System info
snmpwalk -v 2c -c public 192.168.1.1 1.3.6.1.2.1.2  # Interfaces
snmpwalk -v 2c -c public 192.168.1.1 1.3.6.1.2.1.25 # Host resources

# onesixtyone - SNMP community string scanner
onesixtyone -c community.txt 192.168.1.0/24

# snmp-check - Comprehensive SNMP enumerator
snmp-check 192.168.1.1

Common Community Strings (try these):

• public (read-only, most common)

• private (read-write)

• manager

• admin

Information Extracted:

• Device hostnames and descriptions

• Network interface configurations

• Routing tables

• Running processes

• Installed software

• User accounts

• TCP/UDP connections

LDAP Enumeration (Directory Services)

Purpose: Extract organizational structure, user accounts, and configurations from LDAP directories (Active Directory).

Ports: 389 (LDAP), 636 (LDAPS), 3268 (Global Catalog)

Tools and Commands:

# ldapsearch - Query LDAP directory
ldapsearch -x -h 192.168.1.10 -s base namingcontexts

# Extract all users
ldapsearch -x -h 192.168.1.10 -b "dc=example,dc=com" "(objectClass=person)"

# Extract all groups
ldapsearch -x -h 192.168.1.10 -b "dc=example,dc=com" "(objectClass=group)"

# Authenticated search
ldapsearch -x -h 192.168.1.10 -D "cn=admin,dc=example,dc=com" -w password -b "dc=example,dc=com"

# NMAP NSE script
nmap -p 389 --script ldap-search --script-args 'ldap.base="dc=example,dc=com"' 192.168.1.10

Information Extracted:

• Domain structure and organization units

• User accounts with attributes (email, phone, title)

• Group memberships

• Computer accounts

• Password policies

• Service accounts

• Privileged user groups (Domain Admins, Enterprise Admins)

SMTP Enumeration (Mail Servers)

Purpose: Verify email addresses and extract user information from mail servers.

Port: 25 (SMTP), 587 (Submission)

Techniques:

# VRFY - Verify email address
telnet mail.example.com 25
> VRFY admin
> VRFY john.doe

# EXPN - Expand mailing list
> EXPN administrators

# smtp-user-enum - Automated enumeration
smtp-user-enum -M VRFY -U users.txt -t mail.example.com

# NMAP NSE script
nmap -p 25 --script smtp-enum-users --script-args smtp-enum-users.methods={VRFY,EXPN,RCPT} 192.168.1.10

Information Extracted:

• Valid email addresses

• Mail server version and configuration

• Mailing list memberships

• User account existence

DNS Enumeration

Purpose: Discover subdomains, map network infrastructure, and identify services.

Port: 53 (TCP/UDP)

Tools and Commands:

# Zone transfer attempt
dig @ns1.example.com example.com AXFR
host -l example.com ns1.example.com

# DNSenum - Comprehensive DNS enumeration
dnsenum example.com

# Fierce - DNS reconnaissance
fierce --domain example.com

# Sublist3r - Subdomain discovery
sublist3r -d example.com

# Amass - In-depth DNS enumeration
amass enum -d example.com

# NMAP NSE script
nmap --script dns-zone-transfer --script-args dns-zone-transfer.domain=example.com -p 53 ns1.example.com

Information Extracted:

• All DNS records (A, AAAA, MX, TXT, NS, CNAME, SOA)

• Subdomains and related domains

• Mail servers

• Name servers

• SPF, DKIM, DMARC records

• IPv4 and IPv6 addresses

NFS Enumeration (Network File System)

Purpose: Discover exported file systems and mount points on Unix/Linux systems.

Port: 2049

Tools and Commands:

# Show exported shares
showmount -e 192.168.1.10

# NMAP NSE scripts
nmap -p 2049 --script nfs-ls,nfs-showmount,nfs-statfs 192.168.1.10

# Mount NFS share
mount -t nfs 192.168.1.10:/share /mnt/nfs

Database Enumeration

Purpose: Extract database versions, schemas, users, and accessible data.

Common Ports: 1433 (MSSQL), 3306 (MySQL), 5432 (PostgreSQL), 1521 (Oracle)

Tools and Commands:

# MySQL
nmap --script mysql-info,mysql-databases,mysql-users -p 3306 192.168.1.10
mysql -h 192.168.1.10 -u root -p

# PostgreSQL
nmap --script pgsql-brute -p 5432 192.168.1.10
psql -h 192.168.1.10 -U postgres

# MSSQL
nmap --script ms-sql-info,ms-sql-config -p 1433 192.168.1.10
sqsh -S 192.168.1.10 -U sa -P password

Comprehensive Enumeration Toolkit

Essential Tools

Tool	Purpose	Best For
enum4linux	SMB/NetBIOS enumeration	Windows networks
ldapsearch	LDAP querying	Active Directory
snmpwalk	SNMP enumeration	Network devices
dnsenum	DNS enumeration	Domain reconnaissance
nikto	Web server scanning	Web applications
gobuster	Directory brute-forcing	Web paths
ffuf	Web fuzzing	Hidden resources
Nmap NSE	Multi-protocol enumeration	All services

Enumeration Workflow Example

# 1. Identify services (from previous NMAP scan)
# 2. Enumerate each service methodically

# SMB/NetBIOS (if ports 139/445 open)
enum4linux -a 192.168.1.10 | tee enum4linux.txt

# SNMP (if port 161 open)
snmp-check 192.168.1.10 | tee snmp.txt

# LDAP (if port 389 open)
ldapsearch -x -h 192.168.1.10 -s base | tee ldap.txt

# HTTP/HTTPS (if ports 80/443 open)
nikto -h http://192.168.1.10 | tee nikto.txt
gobuster dir -u http://192.168.1.10 -w /usr/share/wordlists/dirb/common.txt | tee gobuster.txt

# SMTP (if port 25 open)
smtp-user-enum -M VRFY -U users.txt -t 192.168.1.10 | tee smtp.txt

Hands-on Enumeration Exercises

Exercise 1: SMB Enumeration

1. Set up a Windows VM or lab environment

2. Run: enum4linux -a <target_ip>

3. Analyze output:

   • What is the domain/workgroup?

   • What users exist?

   • What shares are accessible?

   • What is the password policy?

Exercise 2: DNS Enumeration

1. Choose a domain (your organization or authorized target)

2. Run: dnsenum example.com

3. Attempt zone transfer: dig @ns1.example.com example.com AXFR

4. Document:

   • How many subdomains found?

   • Was zone transfer successful?

   • What services were identified?

Exercise 3: Web Enumeration

1. Identify a web server (authorized testing only)

2. Run: nikto -h http://target.com

3. Run: gobuster dir -u http://target.com -w /usr/share/wordlists/dirb/common.txt

4. Analyze:

   • What directories/files were found?

   • What vulnerabilities were identified?

   • What server version is running?

Enumeration Best Practices

Systematic Approach

• Enumerate all discovered services, not just "interesting" ones

• Document all findings in structured format

• Cross-reference information from multiple sources

• Validate findings before relying on them

Stealth Considerations

• Enumeration is noisy and logged by target systems

• Use appropriate timing and rate limiting

• Consider detection risk vs. information value

• Authenticated enumeration is less suspicious than anonymous

Legal and Ethical

• Enumeration often crosses from passive to active

• Always operate within authorized scope

• Some enumeration techniques may trigger security alerts

• Document all enumeration activities with timestamps

Defensive Countermeasures

Organizations can limit enumeration effectiveness:

• Disable unnecessary services: Close SMB, SNMP on public-facing systems

• Use strong community strings: Change default SNMP communities

• Implement null session restrictions: Block anonymous SMB enumeration

• Disable LDAP anonymous binds: Require authentication

• Configure DNS properly: Disable zone transfers, use split-horizon DNS

• Remove verbose error messages: Don't reveal system details

• Monitor enumeration attempts: Alert on suspicious query patterns

Additional Tools for Information Gathering

Subdomain Discovery

• Sublist3r: Python tool aggregating multiple search engines

• Amass: Comprehensive subdomain enumeration

• Assetfinder: Fast subdomain discovery

• Subfinder: Modern subdomain enumeration tool

Web Application Analysis

• Nikto: Web server vulnerability scanner

• Gobuster: Directory and DNS busting tool

• Ffuf: Fast web fuzzer

• WhatWeb: Web technology identifier

• Wappalyzer: Technology profiler (browser extension)

Credential Harvesting

• theHarvester: Email and subdomain harvester

• LinkedIn2Username: Generate username lists from LinkedIn

• Hunter.io: Email address finder (web service)

Metadata Analysis

• ExifTool: Read metadata from images, PDFs, documents

• FOCA: Fingerprinting Organizations with Collected Archives

• Metagoofil: Metadata extractor for public documents

Key Takeaways

• Information gathering is systematic, not random exploration

• NMAP is the foundational tool for network reconnaissance

• Enumeration provides the granular details needed for exploitation

• Different services require different enumeration techniques

• Always operate within legal and authorized boundaries

• Combine automated tools with manual verification

• Document everything for future reference and reporting

• Defenders should enumerate their own systems regularly

Resources

Books

• "Nmap Network Scanning" by Gordon Fyodor Lyon - The definitive NMAP guide

• "The Web Application Hacker's Handbook" by Dafydd Stuttard - Web enumeration techniques

• "Penetration Testing" by Georgia Weidman - Comprehensive methodology

Official Documentation

• NMAP Documentation: https://nmap.org/book/man.html

• NMAP NSE Scripts: https://nmap.org/nsedoc/

• Enum4linux: https://github.com/CiscoCXSecurity/enum4linux

• NET-SNMP Tools: http://www.net-snmp.org/

Online Resources

• HackTricks: https://book.hacktricks.xyz/ - Enumeration cheatsheets

• PayloadsAllTheThings: https://github.com/swisskyrepo/PayloadsAllTheThings

• Pentesting Tools Cheat Sheet: https://highon.coffee/blog/penetration-testing-tools-cheat-sheet/

Practice Platforms

• HackTheBox: Enumeration-heavy CTF challenges

• TryHackMe: Guided enumeration rooms

• VulnHub: Vulnerable VMs for practice

• PentesterLab: Web application enumeration exercises