TECH TUESDAY

Something happened in late June that every small business owner should understand, not because it changes what good IT protection looks like, but because it clarifies exactly why continuous, around-the-clock protection matters and why the businesses that have it are in a fundamentally different position than those that do not. Sysdig's Threat Research Team documented what they assess to be the first complete ransomware operation driven end-to-end by an AI agent. The operator,

Picture this. A valued employee gives notice. Two weeks pass. They leave on good terms. Then someone needs to log into the project management platform. Or the billing system. Or a vendor portal. And the question nobody thought to ask before their last day surfaces with uncomfortable urgency: who has the password for that? If you are a Roark client, that question does not produce anxiety. It produces appreciation for something Roark built into your environment before you ever

Most small business owners did not hear about what happened on the evening of June 12th. They were not following AI industry news. They were running their businesses. But what happened that Friday night is directly relevant to every business that uses AI tools, is considering using AI tools, or employs staff who are using AI tools whether or not anyone authorized them to. At 5:21 PM ET on June 12, 2026, the U.S. Commerce Department sent a letter to Anthropic's CEO requiring t

Most small business owners will never know how close they came. The attack that could have ended their business arrived, found nothing easy to exploit, and moved on to a softer target. That outcome is not luck. It is the product of a decision made long before the attack arrived: the decision to have the right partner in place. The businesses that absorb a cyber incident and continue operating are not the ones that never get hit. They are the ones that had the right partner, t

If you receive this newsletter, you already have something that most small businesses do not: a technology partner who does not take summers off. That distinction matters more than it might appear, because the data on what happens to businesses without managed IT support during the summer months is stark, well-documented, and entirely preventable. As a Roark client, you sit outside that risk profile. But the businesses around you, your vendors, your clients and your professio

Your team was trained to spot phishing emails. They know not to click suspicious links. They understand that urgent requests for wire transfers deserve a second look. They have been through the annual security awareness module, and they passed. None of that prepared them for the phone call. Vishing (voice phishing) is among the fastest growing and least discussed threat vectors targeting small and mid-sized professional firms today. It does not arrive in an inbox. It does not

There is a conversation happening in boardrooms, partnership meetings, and executive offices across every regulated industry, and it is long overdue. It begins with a question that sounds simple but carries considerable weight: is your firm secure, or is your firm resilient? Most business owners answer without hesitation. They point to their antivirus software, their firewall, their password policy, and their annual security training. They describe their MSP, their compliance

Passwords have been the primary mechanism for securing digital access for more than sixty years. They are also the primary mechanism by which businesses get compromised. A solution became available in 2022 when Apple, Google, and Microsoft committed to passkey support. More than one billion people are already using them. Every major platform your firm runs is ready. In a threat environment where AI is making credential theft faster and more targeted than ever, it’s a good ti

Something significant happened in the cybersecurity world earlier this month, and most small and mid-sized businesses have not yet heard about it. On April 7, 2026, Anthropic, one of the leading artificial intelligence laboratories in the world, announced a new AI model called Mythos. They also announced, in the same breath, that they would not release it to the public. That decision alone should tell you something about what this model is capable of. Anthropic described Myth

For years, firms believed Shadow IT was under control. Standardized systems. Locked-down devices. Approved applications. Centralized identity. It felt contained. Shadow IT has now returned, and this time it does not arrive as unauthorized software installed on a workstation. It arrives quietly, through the browser, through convenience, through curiosity. It arrives as artificial intelligence. Employees are using AI tools today. Not in theory. Not in pilot programs. In active

Most organizations believe they are protected because they have backups. Data is copied. Files are stored. Cloud data is replicated. Somewhere, there is a system that holds a version of the business in case something goes wrong. That belief creates comfort. It also creates risk. A backup is a technical function. Recovery is a business outcome. Confusing the two is one of the most common and costly mistakes leadership teams make. When an incident occurs, no one asks whether ba

Each spring, millions of Americans prepare tax returns, organize financial records, and exchange sensitive information with accountants, payroll providers, and financial advisors. It is a predictable annual cycle. Unfortunately, it is also a predictable opportunity for cybercriminals. Tax season consistently produces a surge in fraud attempts because criminals know two things. First, people are already exchanging financial information. Second, urgency and deadlines make indiv

Modern businesses depend on vendors. Cloud platforms run core systems. Payroll providers handle sensitive employee information. Accounting platforms store financial data. File sharing systems hold client documents. Managed service providers maintain infrastructure. Software companies host customer records. In many firms, dozens or even hundreds of third-party providers quietly support daily operations. This interconnected ecosystem delivers remarkable efficiency. It also crea

Does It Operates in the Open, Governed and Aligned with Your Business? AI is already embedded in the daily work of your firm. Employees use it to draft emails, summarize documents, write code, analyze data, and answer client questions. Some use sanctioned tools. Many use whatever is free and convenient. Leaders who assume their teams are not using AI are operating on hope, not evidence. This moment mirrors the early days of cloud adoption. Tools spread faster than policies. C

Cyber threats evolve every year, yet one attack method continues to cause more direct financial loss to small and mid-sized businesses than any other: Business Email Compromise, or BEC. It is not flashy. It does not rely on sophisticated malware. It does not require a dramatic breach. Instead, BEC exploits something far more reliable, trust. A message appears to come from a managing partner, a client, or a trusted vendor. It requests a payment change, a wire transfer, or sens

For small businesses operating in regulated industries, compliance is often misunderstood. Many leaders assume it is a concern reserved for large enterprises with sprawling compliance departments and in-house counsel. Others treat it as an annual exercise, something to dust off when an auditor calls, or an insurance renewal is due. Both views are dangerously incomplete. In today’s regulatory environment, noncompliance is not a theoretical risk. It is operational, financial, l

The holiday season remains a time of generosity, celebration, and connection. It is also increasingly a season of digital risk. As online shopping continues to dominate how gifts are purchased and transactions are handled, cybercriminals have refined their tactics to blend seamlessly into the noise of the holidays. In 2025, the challenge is no longer recognizing obviously suspicious emails or poorly designed fake websites. Today’s threats are quieter, more personalized, and o

As 2025 draws to a close, it’s worth taking a step back and looking at the year with a clear, unsentimental eye. Not at the buzzwords or the vendor noise, but at the real forces that shaped how small and midsize businesses used technology, defended their data, and kept operations running smoothly. Cybersecurity did not stand still this year, far from it. Threats grew more sophisticated; regulations tightened, insurers became more demanding, and the line between “IT issue” and

The Securities and Exchange Commission has quietly done something very loud. With its 2024 amendments to Regulation S-P, the SEC has turned what used to be a fairly high-level privacy rule into a detailed playbook for how financial firms must prepare for, detect, respond to, and document cybersecurity incidents. The changes touch incident response, vendor oversight, record keeping, and breach notification timelines in ways that many covered firms are still digesting. For Roar

Back in 2020, when the pandemic struck, businesses of every size raced to the cloud. The sudden need for remote access, flexible collaboration, and minimal on-premise dependency made cloud adoption not just a convenience but a necessity. For many small and mid-sized firms, this rapid migration kept operations running and teams connected. But that first phase of the cloud journey, the lift-and-shift sprint, is over. Now, leaders are realizing something important: moving to the