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Answers, including the ones that cost us money.
24 articles about technology risk, written for the person who has to make the decision rather than the person who has to implement it. Nothing here is gated, and none of it requires an email address.
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What should managed IT actually cost?
The question everyone asks and almost nobody answers publicly.
Managed IT vs. hourly vs. in-house vs. hybrid
An honest comparison, including where we are the wrong choice.
Is Sentry CTO the right fit for you?
Who we serve well, and who we genuinely do not.
How to talk to your board about cyber risk
For when leadership starts asking and you need business language.
Everything, newest first
Latest
How to Pass Your Cyber Insurance Questionnaire (Without Lying on It)
Every answer on a cyber insurance questionnaire becomes part of your policy. What insurers verify, how to answer honestly, and which gaps to fix first.
Sep 15, 2026
FAQ
Our I.T. Person Quit: What to Do in the First Week
Your IT person quit and nobody knows the passwords. A seven-day checklist to secure accounts, find what you own, and avoid two costly mistakes.
Sep 1, 2026
Cybersecurity Education
How to Create a Cybersecurity Budget For Small Business
A repeatable framework for deciding what to spend on cybersecurity: impact first, then capabilities, then a 12-18 month roadmap your CFO can defend.
Apr 9, 2026
Cybersecurity Education
How to Talk to Your Board or Investors About Cybersecurity Risk in Business Terms They Understand
Boards disengage when cybersecurity turns technical. A translation framework: outcomes at risk, realistic scenarios, financial impact, decision needed.
Apr 7, 2026
Cybersecurity Education
Best Cybersecurity Software for Small Businesses in 2026
Small businesses used to assume they were too small to be targeted.
Mar 1, 2026
Cybersecurity Education
How to Choose a VPN Service for Secure Internet Browsing (Hint: You Probably Don’t Need One)
Consumer VPNs solve a problem most businesses do not have, and skip the ones they do. When a VPN matters, when it does not, and what to use instead.
Feb 23, 2026
FAQ
What Is Managed IT? A Practical Overview for Finance and Law Firms
For financial firms and law practices, technology failures are compliance events. What managed IT is, what it costs, and how to evaluate a provider.
Feb 2, 2026
Cybersecurity Education
Technology Lifecycle Management: Why Planning Your Technology Matters
Imagine your company loses two full days of productivity because an outdated server crashed without warning.
Jan 15, 2026
Cybersecurity Education
BYOD Security Risks for Law Firms: The “Trojan Keyboard” Problem
Attorneys love their tools. Partners want flexibility. Clients demand confidentiality.
Sep 16, 2025
FAQ
Managed I.T. Services vs Hourly I.T. vs In-House I.T. vs Hybrid: An Honest Assessment of Your I.T. & Cybersecurity Options
Every year, we speak with countless companies that ask what types of I.T. services they really need for their business.
Sep 13, 2025
Cybersecurity Education
The Top 3 AI Threats Businesses Face in 2025
The release of ChatGPT-3 marked a turning point in how we interact with technology. Since then, the pace of AI innovation has skyrocketed.
Aug 10, 2025
Cybersecurity Education
macOS 13 Ventura End of Life: What It Means for Your Business
Ventura stopped receiving security updates in late 2025, and Sonoma is next. What Mac-based businesses should check, and why Intel Macs need a plan.
Jun 10, 2025
Cybersecurity Education
Is a culture of cybersecurity critical for business success?
Tools and providers only go so far. Why the businesses that stay out of trouble are the ones where security became a habit, and how to build one.
Apr 5, 2025
Current Events
Windows 10 End of Life Has Arrived. What It Means for Your Business Now
Windows 10 support ended October 14, 2025. If any of your machines still run it, here is what you are actually exposed to, and the three ways out.
Nov 29, 2024
Cybersecurity Education
Are Your Vendors Secretly Putting Your Business at Risk? How to protect yourself from supply-chain attacks.
Supply chain attacks reach small businesses through the vendors they trust. How to vet suppliers, what to ask them, and how to limit the damage.
Sep 13, 2024
Current Events
Top 3 things businesses should learn from the July 2024 CrowdStrike incident (it's not what you think)
The CrowdStrike incident in July caused a lot of big problems for businesses big and small.
Aug 12, 2024
Cybersecurity Education
5 Easy Yet Powerful Steps Every Business Leader Must Take for Ultimate Cybersecurity
In our ever-changing digital world, do you ever wonder if you’re doing enough to protect your business? Perhaps, you don’t even know where to start!
Jul 25, 2024
FAQ
Is Sentry CTO the Right Fit? A Guide to Choosing Your Cybersecurity and IT Support Provider
An honest breakdown of who we work well with, who we don't, and how to tell the difference before either of us spends a meeting finding out.
Jul 11, 2024
FAQ
How Much Should You Spend on Managed I.T. Services?
Real numbers from real Arizona contracts: what managed IT costs per device, why per-user estimates mislead, and how to budget for your business.
Apr 21, 2024
Sentry CTO - Cybersecurity
Email Is Still How Businesses Get Breached: The Threats That Matter and the Defenses That Work
Most incidents we see start in an inbox, and the expensive ones rarely involve malware. Here is what actually happens, and the layers that stop it.
Mar 6, 2024
Cybersecurity Education
Real-Time Monitoring in Cybersecurity: Who Is Watching Your Network at 2am?
Attackers do their best work when nobody is looking. What continuous monitoring actually does, what it cannot do alone, and the questions to ask.
Jan 4, 2024
Cybersecurity Education
Cyber Insurance: What's the difference from General Liability and why does it matter?
General liability will not pay for ransomware, and a cyber policy will not pay if you cannot prove the controls you claimed. How the two differ.
Aug 21, 2023
Cybersecurity Education
10 Things You Need to Know About Password Managers
Password managers are a great way to keep your online accounts secure. But what exactly are they, and how do they work?
Apr 24, 2023
Current Events
What You Need to Know About the Prescott College Data Breach
Prescott College has suffered a data breach. We’re here to discuss what it may mean for students, staff, and you.
Apr 14, 2023
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