Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro

Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting

In November this year, Senior Offensive Security Consultant Ka Wing Ho was invited to give a talk at Hack Sydney 2024 on the topic of open source intelligence (OSINT) as part of web application penetration testing. This blog is a summary of Ka Wing’s talk and is aimed at junior penetration testers or budding bug bounty hunters wanting to upgrade their web skills.

Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro

Very often junior testers will encounter a 403/404 error when browsing to an IP or hostname, they will then quickly give up and move on, assuming there is nothing there.

The problem with this approach is that the majority of hackers who do this will all end up looking at the same attack surface which has been picked clean, get discouraged, move on, and rinse and repeat.

In Ka Wing’s experience, nine times out of ten, there is something more to these apps that you just can’t see. Read on to find out how one uses OSINT to reveal more about attack surface and the underlying tech stack information for web applications as Ka Wing takes us through the two scenarios below.

They Index Everything? We Google Dork Everything

In this first example, we have a small error message returned by an API endpoint.

Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro

We perform a simple Google Dork by wrapping it in quotes and receive – one measly search result. (Read more about Google Dorking here)

Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro

At first it may seem that we’ve hit a dead end, but by downloading and opening the spreadsheet, we actually get more context and detail.

Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro

The string com.qas.proweb.QasExceptionis a string reminiscent of a Java Stack trace, where the package name is more likely to pop up elsewhere on the Internet in places such as Stack Overflow.

Let’s try dorking for that instead:

Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro

Looks like our assumption was correct! Google tells us that we are up against ProWeb by Experian. Let’s have a look at their website:

Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro

Although not shown, one of the ProWeb manuals we discovered revealed that a special suffix could be sent in requests to retrieve internal information. We included that suffix and were able to disclose relevant internal information such as a backend physical file path.

Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro

We can see now that we’ve managed to escalate an uninteresting error message to a proper information disclosure.

Searching Through Time and Space

The Internet Archive is a treasure trove of information and is especially useful for the collection of data OSINT-style. There are neat tools out there to harvest URLs from archive.org such as waybackurls.

In this example, we are on a web application penetration test, where initial recon steps did not provide much information, even when searching through the Internet Archive.

Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro

However, we have performed enough reconnaissance at this point to know that there were other instances out there, and that the application was based on a vendor product called “ePathway”. Dorking for the default landing page URL revealed the following:

Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro

From here, we can repeat what we just did for our testing instance and harvest the archived URL endpoints from all these other hosts which have been up for longer.

Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro

and mirror them across to our testing instance.

Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro

We can then see that we’ve passively uncovered endpoints for our target which we can spray as a wordlist, some of which aren’t directly advertised on the frontend. From there, any valid hits would result in an additional attack surface.

We’ve also gained valuable insight into how directories and files are named which could educate further directory brute-forcing efforts.

Conclusion

This blog touches on just a few OSINT techniques that can hopefully help you in both your client engagements and side ventures, no matter which web application you encounter.

Defenders may consider some of the following countermeasures:

Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro
Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro
Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro

Stay silent: Give the attackers as little fingerprintable information as possible, making them work harder or switch targets out of boredom/frustration

Adversarial noise: Use false information to deliberately confuse attackers and waste their time

Proper configuration: As a defence-in-depth, only expose what infrastructure is needed and ensure your applications return generic responses where possible

Using OSINT and Fingerprinting to Upgrade Your Web Application Pentesting | Sekuro
Ka Wing Ho
Ka Wing Ho

Senior Offensive Security Consultant, Sekuro

Ka Wing is a Senior Offensive Security Consultant at Sekuro. He is a UNSW alum with a degree in Computer Science majoring in Security. Ka Wing has more than five years’ industry experience in Offensive Security, with a passion for pen testing, bug bounties and Code Reviews.

Scroll to Top

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.