AI Phishing

Emerging Threat: AI vs. Human Deceit

Table of Contents

In today’s digital world, phishing has taken on a new form that blends human tricks with advanced technology. It’s not just about old-fashioned deception anymore.

We’re witnessing a blend of human cunning and the power of artificial intelligence. As we navigate the internet’s complexities, it’s vital to grasp how phishing has evolved – from the tricks used by people to the looming threat posed by AI.

Come with us on this journey to uncover the secrets of phishing, understand how it’s changed, and the new risks it brings, shaking up our ways of defending against online threats.

What is Phishing?

Imagine this scenario: an email lands in your inbox, seemingly too good to be true or pressing with urgency. It might promise lottery winnings, demand immediate action, or mimic a familiar company. But beware – the hook is set. Phishing, the crafty technique employed by cyber tricksters, entices you to reveal sensitive information like passwords, credit card details, or personal data. The catch? It’s all smoke and mirrors.

How do you decipher the genuine from the deception? Scrutinise the fine print. Verify the sender’s email address – does it align with the official one? Spelling mistakes or high-pressure messages should raise alarms. Before clicking any links, hover over them to uncover their actual destinations. And keep in mind: reputable companies won’t solicit sensitive information via email.

Research shows that upwards of 95 percent of cyber breaches within the last decade have involved threat actors and adversaries utilising various types of phishing and social engineering attacks as an initial entry point into organisations of different sizes. The perspective of the malicious actor is quite simply put in the following way: “Why extend resources to research highly technical options of breaching an organisation when you can rely on human weakness without breaking a sweat”.

Phishing isn’t merely an annoyance in the digital world; it’s a lurking threat ready to ambush unsuspecting businesses. The repercussions? Monumental. Beyond the immediate loss of critical data and financial breaches, phishing ravages businesses by staining their reputation, eroding customer trust, and accruing substantial financial losses through regulatory penalties and legal battles. It disrupts day-to-day operations, leading to downtimes and productivity slumps as teams labour to contain the fallout. The aftermath of a successful phishing attack casts a lingering shadow over the stability and sustainability of the targeted organisation, extending far beyond the initial breach. In our deeply interconnected world, the impact of phishing transcends digital boundaries, leaving businesses to grapple with the consequences of falling for a single meticulously crafted deceptive email.

In the ever-evolving landscape of cyber threats, traditional phishing has given way to a new, more sinister player: AI-generated phishing attacks. Unlike their conventional counterparts, these AI-driven assaults are sophisticated, posing elevated dangers to organisations’ cyber security. With an elusive nature, they blur the lines between genuine and fraudulent communication, amplifying the threat of undetectability. 

Defending against these AI-powered tactics requires a recalibration of defence mechanisms, as traditional methods often fall short against their nuanced strategies. 

In this report, we delve into the perils of AI-driven phishing attacks, exploring their inherent dangers, the looming threat of being undetectable, and crucial strategies to fortify organisations against these stealthy adversaries.

The perspective of the malicious actor is quite simply put in the following way: “Why extend resources to research highly technical options of breaching an organisation when you can rely on human weakness without breaking a sweat”.

The dangers of AI driven phishing attacks

The emergence of AI-driven phishing attacks signals a significant shift in the cyber security landscape, introducing a level of sophistication and adaptability that challenges conventional defence strategies. Unlike traditional phishing tactics known for their identifiable flaws such as grammatical errors and lack of personalisation, AI-powered attacks elevate the game substantially. These advanced tools swiftly rectify spelling mistakes and grammar issues, circumventing email filters reliant on exact text matches.

Here’s where it gets intriguing. AI capabilities extend beyond mere error correction, displaying remarkable speed in generating diverse versions of phishing emails. Cyber adversaries leverage AI to traverse social media platforms, extract insights to craft highly personalised messages, pose a substantial challenge in distinguishing genuine correspondence from fraudulent emails.

What’s particularly concerning for cyber security experts is the proficiency of these AI-driven assaults in eluding traditional defence mechanisms. These tactics involve rewriting flagged emails with a professional tone, leveraging AI prowess to evade detection and optimise attackers’ time efficiency. Additionally, with AI tools combing through extensive social media data, attackers can cast a wide net, targeting a broader audience with tailored messages. The emergence of AI-generated phishing poses a formidable challenge, compelling a reevaluation of defence strategies against these intricately personalised cyber threats.

AI-driven potentially outperforms traditional phishing in various ways:

  • Swift error refinement: mistakes in phishing emails like spelling errors and grammar issues are swiftly rectified
  • Bypassing email filters: emails and subject lines are written to bypass traditional email filtering methods
  • Rapid email variations: diverse variations of phishing emails take mere seconds to generate
  • Highly personalised content: generative AI is leveraged to craft highly personalised emails by mining personalised data about their targets from social media platforms
  • Adaptability against detection: emails flagged as spam are swiftly rewritten saving attackers significant time
  • Scalability through data scraping: vast amounts of social media data can be scraped to create realistic messages, enabling attackers to target a broader audience with tailored content
Emerging Threat: AI vs. Human Deceit
AI-assisted vs Traditional phishing attacks

The threat of undetectability

The evolving landscape of AI-driven phishing emails presents a pressing concern: the looming possibility of these attacks becoming exceptionally challenging for detection by both humans and AI-powered email filtering solutions. The intricate nature of AI-generated phishing emails poses significant hurdles for conventional detection methods. AI tools adeptly refine these messages, sidestepping signature-based detection and reputation checks commonly relied upon for spotting fraudulent emails.

Insights from Egress Software Technologies’ threat intelligence team shed light on the formidable challenge these emails present. Out of 1.7 million phishing emails analysed, a staggering 44.9% contained less than 100 characters, with an additional 26.5% containing less than 500 characters. This poses a substantial hurdle for detection systems, particularly those employing AI-based detectors. These detectors require a minimum threshold of characters for reliable analysis – 250 characters for assessment and at least 500 for dependable results. As a significant majority of these phishing emails fall below these requirements, an alarming 71.4% of them evade the capabilities of AI-driven email filtering solutions. This predicament leaves these emails beyond the reach of automated detection, necessitating human intervention for analysis, a resource-intensive process.

Egress also highlighted a concerning trend: human-generated phishing campaigns analysed in 2023, were reported to have implemented at least 2 layers of obfuscation that bypassed 25% of Microsoft’s defences. As these human-led campaigns evolve to include heightened levels of obfuscation, it sets a precedent for what can be expected from AI-generated emails. The likelihood of AI-generated phishing emails with a similar level of obfuscation and greater level of variation of their human counterparts poses an even greater challenge for detection systems, raising concerns about the potential undetectability of these sophisticated attacks in the future.

Other reasons why AI generated emails may be incredibly difficult to detect include:

  • Creative variation: AI-generated diverse variations of phishing emails make it challenging to identify recurring patterns for detection purposes
  • Adaptive evasion tactics: vulnerabilities in specific email filtering or detection systems may be exploited by AI-led evasion techniques
  • Multilingual capabilities: emails in multiple languages can be generated, increasing the reach and potential targets for phishing attacks
  • Targeted content: highly targeted and personalised emails are enabled by AI, incorporating specific details or references that seem authentic to the recipient and are more likely to elicit a response
  • Rapid adaptation: changes in phishing detection methods can be easily adapted to by AI, evolving to bypass newly implemented security measures

Defending the organisation

Defending the organisation against the sophisticated threats posed by AI-driven phishing demands a multifaceted approach that leverages advanced technologies. Unlike traditional email filtering solutions relying on static definition libraries or domain checks, organisations must pivot towards more robust defences. Email filtering solutions that harness the power of Large Language Models (LLMs) such as Natural Language Processing (NLP) and Natural Language Understanding (NLU) offer a more proactive and nuanced defence strategy. These solutions delve beyond superficial indicators, analysing email content for linguistic markers of phishing, understanding context, intent, and anomalies in communication that might indicate potential threats.

The critical divergence between NLP/NLU-based solutions and traditional methods lies in their approach to content analysis. While conventional filters rely on rule-based checks or predefined patterns, NLP/NLU solutions comprehend the nuances and intent behind the text, enabling a more comprehensive understanding of the email content. This capability allows for the identification of subtle linguistic cues indicative of phishing attempts, providing a more effective defence against the evolving sophistication of AI-driven attacks.

To counteract the use of AI by cybercriminals, organisations need to embrace similar technologies for defence. Implementing cutting-edge AI-driven solutions empowers organisations to proactively detect and mitigate AI-generated phishing attempts, enabling a stronger security posture against these evolving threats. However, technology alone cannot guarantee absolute protection.

A recent case highlights this vulnerability—an employee at a client’s organisation received an email that appeared to be an injury claim from a co-worker. The email was highly convincing, leveraging AI-generated text to mimic tone and formatting. Without verifying its authenticity, the employee followed the instructions, unknowingly exposing sensitive company data. By the time the breach was detected, the attacker had already gained access to internal systems.

This incident underscores the necessity of cultivating a culture of cyber awareness alongside technological defences. Educating and continuously training employees to recognise and report suspicious activities or emails remains paramount. The vigilance and responsiveness of all members of an organisation form an indispensable layer of defence, augmenting the capabilities of advanced technological solutions.

Emerging Threat AI vs Human Deceit
How to defend against AI-assisted phishing attacks

Ready to fortify your organisation against evolving phishing threats? Sekuro’s Managed Security Service (MSS) acts as an extension of your security team. We provide fully managed 24/7/365 monitoring, detection, triage and response services. Secure your organisation today.

Sekuro's Latest Insights

Get in Touch

Discover the Smarter Way to Transform Your Organisational Security – Connect with Our Experts Today.

Complete the form and we will get in touch within 24 hours. 

Aidan Tudehope

Co-Founder of Macquarie Technology

Aidan Tudehope, Co-Founder of Macquarie Technology

Aidan is co-founder of Macquarie Telecom and has been a director since 1992. He is the Managing Director of Macquarie Government & Hosting Group with a focus on business growth, cyber security and customer satisfaction. 

Aidan has been responsible for the strategy and execution of the investment in Intellicentre 4 & 5 Bunkers, Macquarie Government’s own purpose-built Canberra data centre campus. This facility is leveraged to deliver Secure Cloud Services and Secure Internet Gateway.

With a unique pan-government view on the cyber security landscape, we are invested in leading the contribution from the Australian industry on all matters Cyber policy related.

Aidan holds a Bachelor of Commerce Degree.

James Ng

CISO, Insignia Financial

James Ng, CISO, Insignia Financial

James is a leader with a range of experience across various cyber security, technology risk and audit domains, bringing a global lens across a diverse background in financial services, telecommunications, entertainment, consulting and FMCG (Fast Moving Consumer Goods). He is currently the General Manager – Cyber Security at Insignia Financial and most recently was at AARNet (Australia’s Academic and Research Network) where he oversaw a managed Security Operations Centre (SOC) capability for Australian universities. Prior to this James was the acting Chief Information Security Officer for Belong and led the cyber governance and risk team at Telstra.

Noel Allnutt

CEO, Sekuro

Noel Allnutt CEO | Sekuro

Noel is a driven and award-winning IT leader. He has a passion for developing great teams and accelerating client innovation, and in enabling organisations to create a secure and sustainable competitive advantage in the digital economy. Noel also hosts the ‘Building Resilience Podcast,’ which explores the world of sport and deconstructs the tools and ethos of world-class athletes that can help create growth and optimise business and life.

Audrey Jacquemart

Bid Manager, Sekuro

Audrey Jacquemart, Bid Manager, Sekuro

Audrey is an innovative cybersecurity professional with a versatile profile spanning across Product Management, Presales and Delivery. She has worked within organisations from start-ups to large international organisations in Europe and APAC before joining Sekuro.

Nicolas Brahim

Principal Consultant, CRP and OT

Nicolas Brahim, Principal Consultant, CRP and OT

Nico leads Sekuro’s Cyber Resilience Program and OT Cybersecurity, ensuring continuous support and effective program execution for our clients. With over a decade in the security industry, including the creation and leadership of several Security Programs for IT and OT across Australia, New Zealand, Argentina, Chile and the US, his core philosophy emphasises an equal balance of people, process, and technology in delivering actionable and simple solutions.

Trent Jerome

Chief Financial Officer, Sekuro

Trent Jerome

Trent is a seasoned CFO with over 30 years’ experience in Finance. Trent has broad experiences across Capital raises, debt financing, M&A and business transformation. He is a CPA and member of AICD. Trent works with Boards around risk and risk mitigation plans and assists Boards in navigating the risk mitigation versus cost conversation.

Ada Guan

CEO and Board Director, Rich Data Co

Ada Guan, CEO and Board Director, Rich Data Co

Ada is the CEO and Co-founder of Rich Data Co (RDC). RDC AI Decisioning platform provides banks the ability to make high-quality business and commercial lending decisions efficiently and safely. With over 20 years of global experience in financial services, software, and retail industries, Ada is passionate about driving financial inclusion at a global scale.

Before launching RDC in 2016, Ada led a Global Client Advisor team at Oracle Corporation, where she advised Board and C-level executives in some of the largest banks globally on digital disruption and fintech strategy. She also drove Oracle’s thought leadership in banking digital transformation for Global Key Accounts. Previously, Ada implemented a multi-million dollar program to deliver a mission-critical services layer for Westpac Bank in Australia and formulated the IT strategy that was the basis of an $800m investment program to transform Westpac’s Product and Operation division and complete the merger with St. George Bank. Ada is an INSEAD certified international director and holds an EMBA from the Australia Graduate School of Management, and a Master of Computer Engineering from the University of New South Wales, Australia. She also graduated from the Executive Insight Program at Michigan University Ross Business School and IESE Business School.

Megan Motto

Chief Executive Officer, Governance Institute of Australia

Megan Motto, CEO, Governance Institute of Australia

Megan Motto is Chief Executive Officer of Governance Institute of Australia, a national education provider, professional association and leading authority on governance and risk management. The Institute advocates on behalf of professionals from the listed, unlisted, public and not-for profit sectors.

Megan has over 25 years of experience with large associations, as a former CEO of Consult Australia, as well as holding significant positions in Australia’s built environment sector and business chambers.

She is currently a director of Standards Australia, a member of the ASIC Corporate Governance Consultative Panel and a councillor of the Australian Chamber of Commerce and Industry (ACCI) where she chairs the Data, Digital and Cyber Security Forum.

Megan’s expertise spans governance, risk management, public policy and education. She holds a Bachelor of Arts/Bachelor of Education, a Masters of Communication Management and a Graduate Diploma of Corporate Governance and Risk Management. She is a Fellow of the Governance Institute of Australia, the Chartered Governance Institute and the Australian Institute of Company Directors and is also a member of Chief Executive Women. Megan is also an Honorary Life Trustee of the Committee for Economic Development of Australia (CEDA) and was a 2014 recipient of the AFR/Westpac 100 Women of Influence.

Shamane Tan

Chief Growth Officer, Sekuro

Shamane Tan, Chief Growth Officer, Sekuro

Sekuro’s Chief Growth Officer, Shamane Tan, is passionate about uniting minds and experiences, excelling in aligning C-Suite and Board members with cyber security imperatives. As the author of “Cyber Risk Leaders,” she unravels executive communication nuances and distils C-Suite expectations. 

Her work extends to “Cyber Mayday and the Day After,” a roadmap for navigating crises by mining the wisdom of C-level executives from around the globe. It’s filled with interviews with managers and leaders who’ve braved the crucible and lived to tell the tale. Her most recent book, “Building a Cyber Resilience: A Cyber Handbook for Executives and Boards,” was featured on Forbes Australia’s top list of books for CEOs. 

Shamane has also founded a transcontinental cyber risk and executive meetup spanning Sydney, Melbourne, Adelaide, Perth, Singapore, the Philippines, and Tokyo, fostering mentorship, women’s empowerment and thought leadership. As a strong advocate for the importance of having a voice and helping others use theirs, Shamane Tan has spoken at TEDx and global conferences, including FS-ISAC, RSA, Silicon Valley, Fortune 500 and ASX companies. 

Recipient of the IFSEC Global Top 20 Cybersecurity Influencer award and named among the 40 under 40 Most Influential Asian-Australians, Shamane leverages her unique fusion of technical prowess and business acumen to help organisations progress on their security maturity journey.

David Gee

David Gee, CIO, CISO, NED, Board Advisor & Author

 

David Gee, CIO, CISO, NED, Board Advisor & Author

David has just retired in July 2024 and is building out his portfolio. He is an Advisor with Bain Advisory Network and also an Advisor to JS Careers (Cyber Recruitment) and Emertel (Software Commercialisation).

He is a seasoned technology executive with significant experience and has over 25 years’ experience in CIO and CISO roles across different industries and countries. At Macquarie Group David served as Global Head Technology, Cyber and Data Risk. Previously was CISO for HSBC Asia Pacific. His career as a CIO spans across multiple industries and geographies including – Metlife, Eli Lilly and Credit Union Australia. He was winner CIO of the Year 2014, at CUA where he successfully completed a significant Transformation of Core Banking, Online and Mobile Banking systems.

David is past Chairman for the FS-ISAC Strategy Committee and awarded Global Leaders Award in 2023 for his contributions to the cyber security industry. A regular conference keynote speaker and 150+ published articles for CIO Australia, Computerworld, iTnews and CSO (Cyber Security), David now writes for Foundry CIO.com and AICD.

His most recent book – the Aspiring CIO & CISO was published in June 2024 and David is writing his second – A Day in the Life of a CISO with a number of CISOs from around the world for 2025.

Naomi Simson

Co-founder, Big Red Group and Former Shark Tank Judge

Naomi Simson, Co-founder, Big Red Group

INTRODUCTION

For 25 years as an entrepreneur, Naomi Simson has been bringing people together whether it’s with her business experience, her speaking or writing. Passionate about small business and local community, Naomi is considered a home grown success story.

Naomi had a corporate career with Apple, KPMG, IBM and Ansett Australia prior to becoming an entrepreneur. She is a prolific blogger, podcaster and business commentator, and appeared as the #RedShark in four seasons of Shark Tank Australia and she appears regularly on ABC The Drum. She is a non-executive director at Big Red Group, Australian Payments Plus, Colonial First State and Weebit Nano, as well as the Cerebral Palsy Research Foundation and the University of Melbourne Business and Economics Faculty.

A true business leader and influencer, with more than 2.7 million LinkedIn followers, Naomi is Australia’s most followed person on the business networking platform. She has four seasons of her podcast ‘Handpicked’, and she has authored two best-selling books Live What You Love, and Ready to Soar, and is sought after speaker.

FULL BIO

For 25 years Naomi has been bringing people together whether it’s with her business experience, her speaking or writing. She is a strong advocate of business owners.

Known as an entrepreneur and business leader; following the growth of RedBalloon which she founded in 2001, Naomi co-founded the Big Red Group (BRG) in 2017.

Naomi had a corporate career with Apple, KPMG, IBM and Ansett Australia prior to becoming an entrepreneur. She is a prolific blogger, podcaster and business commentator, and appeared as the #RedShark in four seasons of Shark Tank Australia. She is a non-executive director at Big Red Group, Australian Payments Plus, Colonial First State and Weebit Nano. As well as the Cerebral Palsy Research Foundation and the University of Melbourne Business and Economics Faculty.

A true business leader and influencer, with more than 2.7 million LinkedIn followers, Naomi is Australia’s most followed person on the business networking platform. She has authored two best-selling books Live What You Love, and Ready to Soar, and is an engaging, humorous and insightful speaker. She has four seasons of her Podcast – Handpicked.

Naomi is relatable across a broad variety of audiences and topics, often drawing on her personal experiences to provide thoughtful and valuable views into topics; including the customer obsession, intentional leadership, growth mindset, personal development. She is a regular panellist on ABC The Drum.

Peter Ngo

Product Line Manager, Global Certifications, Palo Alto Networks

Peter Ngo | Sekuro

Peter leads the Commercial Cloud, Global Certifications organisation at Palo Alto Networks which oversees global cloud security compliance efforts to various frameworks and standards including IRAP, SOC 2, ISO, PCI, C5, ISMAP, and IRAP and more for 25+ cloud products.

He has held many roles over the years covering areas of IT Operations, and Governance, Risk, & Compliance (GRC) for a wide range of industries including technology, insurance, and manufacturing.

Peter holds various security and professional certifications, including the CCSP, CISSP, PCI ISA, CISA, CISM, CDPSE & ISO Lead Auditor, in addition to a Master of Science degree in Information Assurance. 

Jack Cross

CISO, QUT

Jack Cross | Sekuro

Jack Cross is an experienced business leader with expertise in digital technologies and risk management. Through a steadfast commitment to integrating people, processes, and technology, he champions the fight against cyber threats while mitigating organisational risks. 

Over the past 15 years, Jack has navigated diverse leadership roles within the Defence and Education sectors, honing his skills in steering multidisciplinary teams through intricate and sensitive technical landscapes. In addition to this experience, he holds numerous formal qualifications such as: a Master of Systems Engineering (Electronic Warfare); CISSP; and CISM certifications.

Nadene Serman

Global CTO, Infotrack

Nadene Serman | Sekuro

Nadene Serman is a leading IT executive with a proven track record spearheading first-of-its-kind technology and business transformation for some of the most prominent organisations globally and in Australia. As the Global Chief Technology Officer of InfoTrack, she is a key protagonist of innovation as an enabler of InfoTrack’s next stage growth. Her energy, commercial acuity and strategic capability have fueled her success.

Nadene leads with clarity, transparency and urgency, uniting people in complex, multi-layered technology and business execution, and go-to-market transformation and innovation. She tackles and resolves complex and seemingly intractable challenges while building support and collaboration – even in times of crisis. Her people-first, ‘think straight, talk straight’ approach makes her a formidable force.

John Doe

President Great Technology

Cyber Resilience Program | Sekuro

Lorem ipsum dolor sit amet, consectetur adipiscing elit. Ut elit tellus, luctus nec ullamcorper mattis, pulvinar dapibus leo.