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The one where we impersonated the Head of IT

A routine day at the office. A familiar face. A trusted voice. That’s all it took to open the door to an organization’s most sensitive systems. For a major retailer, it wasn’t malware or a zero-day exploit that compromised their Google Workspace. It was us, pretending to be their Head of IT.

A routine day at the office. A familiar face. A trusted voice. That’s all it took to open the door to an organization’s most sensitive systems. For a major retailer, it wasn’t malware or a zero-day exploit that compromised their Google Workspace. It was us, pretending to be their Head of IT.

The breach didn’t start with code. It started with a conversation. One built on urgency, authority, and just enough detail to sound legitimate.

This is a story about how social engineering slipped past every technical control. And why, in the fight to protect your digital environment, the human element is still the easiest way in.

Person standing outside office building, looking at a phone, suggesting real-world surveillance or reconnaissance.

The scenario

Human manipulation often proves more effective than technical exploits. With just 48 hours of intelligence gathering, we uncovered the pathway to an entire digital environment.

Our target: an unsuspecting employee with the keys to the organization’s Crown Jewels.

Our method: the art of social engineering.

Within days, we had gained full administrative access to their Google Workspace, the beating heart of their business operations. What started as a simple social engineering exercise transformed into complete control of their critical systems, proving once again that even the most robust businesses have weaknesses in their security posture.

The challenge

Modern cybersecurity isn’t just about strong passwords and firewalls; it’s about understanding the human element. In this case, our mission was to test whether a household name retailer’s digital defenses could withstand a targeted social engineering attack aimed at their Google Workspace environment.
The question wasn’t if we could get in, but how quickly and thoroughly we could compromise their systems through purely human-based tactics.

The approach

We began with reconnaissance. For two days, we performed meticulous OSINT (Open Source Intelligence) gathering, sifting through publicly available information like digital detectives.

The breakthrough came when we discovered a Facebook data breach containing valuable employee information. With this intelligence in hand, we identified two promising contacts within the organization. Through careful verification against LinkedIn and Facebook profiles, we confirmed the identity of our primary target: the Head of IT.

Further investigation revealed a critical detail, staff members had listed Slack as a communication tool on their LinkedIn profiles, giving us insight into their internal communication methods.

The narrative

We crafted a compelling narrative: a suspected cyber breach requiring immediate action. Using spoofed contact information, we reached out to our target with urgency, instructing them to avoid communicating with colleagues about the potential “internal threat.” We convinced them to log out of Slack, effectively isolating them from any potential verification checks with coworkers.

The final step was the tipping point: we persuaded the target to reset their Google Workspace password and share it with us for “system cleansing.” To ensure persistent access, we added an additional phone number to their authentication portal, creating a backdoor for future access to critical applications.

The breach

The moment of compromise came swiftly. With the password in our possession and an alternative authentication method established, we gained complete administrative control over their Google Workspace environment. The keys to their entire digital environment, including documents, calendars, contacts, and critical business applications.

What made this breach particularly significant was its stealth. The target believed they were collaborating with their own IT leadership to resolve a security threat, never realizing they were actually creating one.

By isolating them from their normal communication channels, we eliminated any chance of verification that might have exposed our ruse.


The outcome


In less than a week, using nothing but publicly available information and persuasive communication, we gained complete administrative control over a business-critical system.

We established persistent access that could have allowed for ongoing surveillance, data exfiltration, or further lateral movement within their network.

Beyond our primary objective, we uncovered something unexpected: an undocumented warehouse address absent from their domain records. This physical location represents a potential avenue for future physical penetration testing, a reminder that cybersecurity and physical security are inextricably linked.

This intelligence reveals a fundamental truth about modern cybersecurity: technical defenses are only as strong as the human element supporting them. The retailer’s systems weren’t compromised through sophisticated malware or zero-day exploits, they were breached through trust manipulation and social pressure.


What if?

What if this had been a real attack? Without our intervention, a real-world attacker could have caused them a severe security incident with far-reaching consequences.

Had this been a malicious actor, they could have maintained access indefinitely, extracting sensitive customer data, financial information, or intellectual property without detection.

Constant threat demands constant, targeted attack. The significant gap between this organization’s perceived level of cyber risk and its actual exposure could have resulted in devastating consequences, financial losses, reputational damage, and business disruption.


What would an attacker find if they targeted you today?

By engaging with CovertSwarm, organizations gain the advantage of having ethical hackers applying pressure to every part of their business, at every depth, securing them through and through.

Our approach doesn’t just identify vulnerabilities, it helps businesses understand how those vulnerabilities could be exploited in the real world, creating more resilient security cultures where employees become the strongest link rather than the weakest.

Don’t wait for the attack that’s already in progress. Take control of your cybersecurity posture today with constant, targeted offensive security that outpaces your real adversaries.