TryHackMe — OhSINT Walkthrough

Investigator: Ahad Parvaiz
Date: 31 August 2025
Subject: Oliver Woodflint (@OWoodflint)
Difficulty: Easy
Room Link: OhSINT on TryHackMe
Points Earned: 210

Introduction

Open-Source Intelligence (OSINT) is the process of collecting and analyzing publicly available information. In cybersecurity, OSINT is crucial for reconnaissance, allowing analysts and penetration testers to map a target’s digital footprint.

The OhSINT challenge on TryHackMe demonstrates how much information can be uncovered from a single file. By analyzing image metadata, performing username lookups, and pivoting across multiple platforms, we can build a detailed profile of an individual.

Objective: Extract hidden information from the provided image and answer specific questions using OSINT techniques. This exercise helped me understand how different tools and platforms can be combined to track online identities and uncover sensitive information.

Tools Used

• Exiftool: Metadata extraction
• Google Search / Username Enumeration
• WordPress / GitHub / Twitter Searches
• Wigle.net: Wi-Fi SSID lookup

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Methodology

The investigation began with the provided image file WindowsXP_1551719014755.jpg.

kUsing metadata analysis, online searches, and OSINT tools, I extracted key information to answer the challenge questions.

Q1. What is this user’s avatar?

Process:

• Ran exiftool on the image → found copyright field containing the username OWoodflint.
• Google search for the username led to a Twitter profile.

Answer: Cat image

Q2. What city is this person in?

Process:

• Google search for OWoodflint → Github profile revealed location.

Answer: London

Q3. What is the SSID of the WAP he connected to?

Process:

• There is a post on Twitter which revealed the Bssid: B4:5D:50:AA:86:41.
• Using wigle.net, I searched this id and the SSID of the WAP.

Answer: UnileverWiFi

Q4. What is his personal email address?

Process:

• Found email in GitHub Readme.txt associated with OWoodflint.

Answer: OWoodflint@gmail.com

Q5. What site did you find his email address on?

Answer: GitHub

Q6. Where has he gone on holiday?

Process:

• Reviewed blog content → identified holiday location.

Answer: New York

Q7. What is the person’s password?

Process:

• Found hidden password on Wordpress blog page.

Answer: pennYDr0pper.!

Findings Summary

Conclusion

The OhSINT challenge highlighted how much valuable information can be gathered from a single piece of publicly available data. Starting with just an image file, I was able to extract metadata, identify a username, and pivot across platforms to gather details like location, Wi-Fi SSID, email, and credentials.

This exercise reinforced the importance of being careful with the data we share online. For security professionals, it demonstrates practical OSINT use in reconnaissance and red teaming. For everyday users, it shows how easily personal data can leak unintentionally.

Overall, this challenge was a valuable learning experience that strengthened my skills in metadata analysis, online investigation, and critical thinking within an OSINT workflow.

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