Skip to content

Articles

The IT Dilemma – Field Notes on Technology Risk

Practical commentary on IT operations, cybersecurity, infrastructure resilience, leadership mistakes, vendor gaps, and the business problems hiding behind technology failures.

What This Covers

The IT Dilemma is built from real-world field experience, lessons from complex environments, and AI-assisted drafting that turns operational pain into useful business insight.

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

cyber insurance cybersecurity budget EDR MFA Microsoft 365 security stack The IT Dilemma

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.

June 28, 2026

The Enterprise Blind Spot

cybersecurity enterprise risk IT governance physical security security awareness The IT Dilemma

There is an exercise I like to run with business owners who want to understand their real security posture. I walk in wearing a plain t-shirt, sit down at a computer in a position of authority, and wait. In most cases, nobody questions me for 20 to 30 minutes.

May 28, 2026

The Next AI Bottleneck Isn’t Intelligence. It’s Electricity.

AI compute AI infrastructure data centers dealership technology digital transformation distributed data centers enterprise IT operational maturity power grid SPAN technology strategy XFRA

SPAN’s XFRA announcement is more than a data center product launch. It is a signal that the next phase of AI adoption will be shaped by electrical infrastructure, distributed compute, and operational readiness.

May 28, 2026

Most Security Problems Begin Long Before the Attack

Business cybersecurity infrastructure Tech

Modern cyberattacks move too quickly for businesses to rely on last-minute response. Resilience has to be built before the clock starts ticking.

May 27, 2026

Your Network Is Part of Your Customer Experience

Business infrastructure Networking Tech

A practical executive article on why network reliability quietly shapes customer experience, employee confidence, and operational trust.

May 27, 2026

Working Internet Is the Lowest Standard

Business infrastructure Networking Tech

A business-focused article explaining why “the internet works” is too low of a standard for modern operations.