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Cybersecurity

Real-world cybersecurity lessons covering identity risk, MFA gaps, compliance, incident response, and security decisions that affect business resilience.

18 articles

June 29, 2026

The Flat Network Problem

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When I connect to a customer's guest Wi-Fi as part of an assessment, I run a LAN scan to show them exactly what is visible to anyone who walks through the door. What shows up would surprise most business owners - and your guest Wi-Fi may be putting a stranger on the same road as your payroll server.

June 28, 2026

The Saturday Morning Test

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It is Saturday morning. The systems are down. Nobody can log in. What happens next tells you everything about whether you actually have an incident response plan - or whether you just think you do.

June 28, 2026

The Accidental Custodian

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If you are the person keeping the technology running while doing your actual job - thank you. You are the reason the business kept running. Now I need to tell you something hard: you should not be doing this job. And the longer you do, the more risk you are quietly building into the company you have worked so hard to protect.

June 28, 2026

The Policy the Hacker Is Looking For

cyber insurance document security network security ransomware The IT Dilemma

When ransomware hits, attackers do not guess at a ransom number. They read your email first. If your cyber insurance policy is anywhere in your digital environment, they know exactly how much to demand - because they know exactly how much your insurer is prepared to pay.

June 28, 2026

A Copy Is Not a Backup

3-2-1 backup rule backup cloud storage disaster recovery ransomware SSO The IT Dilemma

When you open your computer and click on OneDrive or Dropbox, do you enter a separate username and password? For most people the answer is no. That convenience has a name - Single Sign-On. And if ransomware hits, it may be the reason your backup is gone too.

June 28, 2026

The Insurance Trap

cyber insurance cybersecurity compliance FTC Safeguards Rule insurance claim denial The IT Dilemma

There is a moment I have seen play out more than once. A business gets hit, files a claim against the cyber insurance policy they have been paying for - and the claim comes back denied. The blame moves fast. But the application had one signature on it.

June 28, 2026

What Is a vCISO

CISO cybersecurity strategy IT governance security leadership The IT Dilemma vCISO

When the conversation turns to security leadership, business owners give one of two answers: they cannot afford a CISO, or they point to Jon who games on weekends and built the network. Neither answer is a security strategy.

June 28, 2026

What Cybersecurity Costs

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When business owners ask what cybersecurity costs, the conversation is almost always dead before it starts. Here is what a real security stack actually costs for a 50-person organization - and why the number is not the real conversation.

June 28, 2026

The True Downtime Cost Framework

business continuity cyber insurance cybersecurity downtime cost ransomware The IT Dilemma

If someone told you to lock your doors, power everything off, and not open again for 30 days - no sales, no service, no revenue - could you afford it? That is exactly what a serious cyberattack asks of you. The ransom is the smallest number on the list.