Articles
Practical commentary on IT operations, cybersecurity, infrastructure resilience, leadership mistakes, vendor gaps, and the business problems hiding behind technology failures.
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
People ask me sometimes why I do this. The honest answer is that I love it. Not just the problem-solving - the ritual of it, the precision of it, the quiet satisfaction of watching a business run the way it was built to run.
June 28, 2026
This checklist is built for anyone who has responsibility for technology - whether that is a Tier 1 tech, an accidental IT manager, a vCISO, or a business owner. Ten minutes. Four pillars. One question: does anything look wrong?
June 28, 2026
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
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
Let me tell you what is happening in your business right now. Your employees are using AI. Not some of them. Not the tech-savvy ones. All of them. For everything they can think of. And mixed in with the lunch orders and trivia questions is your most sensitive business data.
June 28, 2026
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
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
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
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
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.
