Think Like an Attacker: 4 Red Flags That Weaken Cybersecurity Posture

What if your greatest cybersecurity weakness isn’t a complex exploit, but something much simpler, like a missed MFA enrollment or a weak password reused from a decade-old breach? 

In a recent expert-led session hosted by IT Weapons, All Covered, and Depth Security, we explored real-world tactics used by attackers to breach business networks along with the simple (yet critical) steps security teams can take to stay ahead. 

Jake Reynolds, Director of Offensive Security Services at Depth Security (an All Covered company), brought 28+ years of red-team expertise to the table. His message was clear: you don’t need a zero-day to suffer a breach. Most attackers don’t even need to try that hard. 

Here are four attacker footholds to take seriously:

1. Social Engineering Still Works (and It Works Well)

Even with all the tools in place, human error remains a top entry point. From spear phishing to spoofed executive emails, attackers are constantly refining ways to manipulate users. The fix? Layered email defenses, regular user education to increase cybersecurity awareness, and clear internal processes for sensitive requests.

2. Password Spraying Is Surprisingly Effective

Attackers don’t brute-force passwords—they go horizontal. With just one common password and a list of usernames (often harvested from LinkedIn or past breaches), they’ll patiently probe until they find a hit. Weak password policies, lack of ban lists, and outdated login portals make it easy.

3. Multifactor Authentication Gaps Can Undo Everything

Multifactor authentication only works if it’s everywhere. Attackers target enrollment loopholes, forgotten disaster recovery endpoints, or exploit push fatigue to slip through. If any system falls outside your MFA net, it’s an open door.

4. Unpatched Vulnerabilities Linger Longer Than You Think

Despite better tools, many businesses still expose old web apps or services that haven’t been updated—or worse, they’re unaware they’re even online. Attackers know this, and they’re scanning for them 24/7. 

Where to Begin to Strengthen Cybersecurity Posture? Start Outside-In. 

As Jake pointed out, organizations don’t need massive budgets to strengthen their defenses. A focused external penetration test is one of the most effective starting points for identifying cybersecurity vulnerabilities. It reveals real-world risk from an attacker’s perspective and helps prioritize what matters most. 

Want the full webinar experience? 
Watch the recording here.