Inside My First-Round Red Team Interview: Networking, Web Exploits, and Windows Attacks

Inside My First-Round Red Team Interview: Networking, Web Exploits, and Windows Attacks

A behind-the-scenes look at my Red Team interview. This was a first-round technical and experience-based interview, covering networking, operating systems, programming, web vulnerabilities, and Windows authentication attacks.


Context & Participants

This interview was with the department lead responsible for physical security and red team operations.

The session started with a brief introduction of ourselves and moved into technical questions, followed by discussion of the role, structure, and expectations for new hires.


Company & Role Overview

The organisation offers three main services:

  1. Red Team: Unlimited penetration testing on a subscription model.
  2. Blue Team: Incident response and SOC services.
  3. Black Team: Managed IT services, including IoT infrastructure and client support.

The role I was interviewing for is within the Red Team, focusing on offensive security, penetration testing, and client engagements.

Exposure includes web applications, networks, and physical security assessments.


Candidate Background & Experience

  • Freelance penetration testing while studying at the University of Bedfordshire.
  • Practical experience writing reports and testing both web applications and networks.
  • Part-time work during studies.
  • Familiarity with tools, labs, and hands-on learning environments.


Interview Questions & Play-by-Play

Networking

  • TCP vs UDP: Explained TCP as connection-oriented and reliable; UDP as faster and connectionless.
  • TCP Handshake & Termination: Discussed SYN, SYN/ACK, ACK; touched on FIN for teardown.
  • ARP & ARP Spoofing: Explained how ARP resolves IP addresses to MACs; ARP spoofing manipulates cache to redirect traffic.
  • VLAN: Described a virtual LAN as a method to isolate traffic on the same physical network.
  • Switch vs Router: Differentiated switch (Layer 2) from router (Layer 3).
  • Subnetting: Explained network vs host bits, masks, and calculation of subnets.

Operating Systems

  • Purpose of OS: Manages hardware and resources, provides interface for applications.
  • Kernel vs User Space: Kernel manages resources, user space is where applications run.
  • Running a Program: Discussed loading an executable into memory and process creation.
  • System Calls & Context Switching: Touched on process interaction with kernel and CPU switching between processes.
  • Process vs Thread: Compared independent processes vs lightweight threads sharing memory.
  • Memory Calculation: Calculated bytes in a million 32-bit integers (~4 MB).

Programming Concepts

  • Iteration vs Recursion: Iteration as loops, recursion as self-calling functions.
  • Stack vs Heap: Stack holds local variables (fast, LIFO), heap is dynamically allocated memory (slower, fragmented).
  • eval() in Python: Explained it executes code from a string input.

Web Vulnerabilities

  • SQL Injection: Discussed in-band, out-of-band, and blind SQLi types.
  • Cross-Site Scripting (XSS): Identified multiple types; DOM-Based XSS mentioned briefly.

Windows / Active Directory

  • Kerberos Authentication: Explained basic mechanism.
  • AS-REP Roasting: Covered password hash extraction from Kerberos responses.
  • SMB / File Shares: Identified TCP port 445 and attacks possible if SMB signing is not enforced.


Role & Company Discussion

The interviewer described high performer traits:

  • Ability to work under pressure
  • Adaptability to different testing types
  • Willingness to learn and contribute to the team

The organisation is growing rapidly, offering exposure to all aspects of offensive security.

Structure for career progression is being developed, including junior → senior → team lead → head roles.

Overtime is available at £50/hour for tests that extend beyond normal working hours.


Closing

The interview concluded with confirmation that I would advance to the final round, which will cover deeper operating systems fundamentals, programming concepts, and additional offensive security topics.

← Back for Round Two - CyberSec Analyst... Cacti CVE-2025-24367 – Authenticated ... →