What 2025 Taught Us: Key Cyber Trends We Navigated Together and What’s Ahead for 2026
- Roark Tech Services
- 2 days ago
- 6 min read
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 “business risk” blurred even further. Yet the most important story of 2025 is not about the challenges themselves, but about how our clients rose to meet them. Quietly. Steadily. And with Roark walking beside them every step of the way.
This year reinforced a truth we’ve believed for decades: good IT is not reactive. It is anticipatory. The firms that weathered 2025 with confidence were the ones supported by strong foundations, disciplined processes, and a technical partner capable of staying several steps ahead.
Today, we break down the major trends of the year, what they meant for business leaders, and how Roark’s proactive work helped our clients navigate them with confidence, and often without disruption.
THE RISE OF AI-DRIVEN ATTACKS
If 2024 was the warm-up, 2025 was the year artificial intelligence fully entered the offensive playbook. Attackers used AI not only to craft more convincing phishing emails, but to mimic voices, create deep-fake instructions, and generate real-time responses during social engineering calls.
For small businesses, especially those handling financial data, this shift mattered. Traditional “gut check” techniques stopped working. Emails and messages became nearly indistinguishable from legitimate correspondence.
How Roark Stayed Ahead:
Build and update written policies
Maintain clean evidence for audits, regulators, and cyber insurers
Strengthen vendor due diligence and contract language
Update incident response plans to comply with new notification timelines
Implement better logging, monitoring, and documentation
Clients did not face these attacks blindly. They faced them with preparation, training, and a defensive stack configured for the modern threat landscape, not for threats of years past.
THE EXPANDING REGULATORY LANDSCAPE
From the amended Regulation S-P to updated state privacy laws, 2025 was the year when regulators made it clear that cybersecurity is no longer an IT preference; it is a compliance mandate.
While many regulations target large institutions, their expectations cascade directly to small firms through vendor oversight, client due diligence, and insurance requirements.
Roark’s Work This Year Helped Clients
Build and update written policies
Maintain clean evidence for audits, regulators, and cyber insurers
Strengthen vendor due diligence and contract language
Update incident response plans to comply with new notification timelines
Implement better logging, monitoring, and documentation
This was not reactive work. It was proactive governance, putting clients ahead of the regulatory curve rather than scrambling after it.
CYBER INSURANCE BECAME MORE DEMANDING
Cyber insurers spent 2025 tightening eligibility criteria, raising premiums, and requiring detailed proof of technical controls. Basic MFA and antivirus no longer satisfy carriers.
They want hard evidence of:
Endpoint detection and response
Privileged access controls
Immutable backups
Documented policies
Role-based access restrictions
Vendor oversight practices
Incident response testing
Many businesses discovered that insurance applications had become miniature audits!
Roark Helped Clients Secure Coverage By:
Providing documented evidence of controls aligned with SOC 2 and NIST
Implementing required security protection
Running pre-application readiness reviews
Communicating directly with carriers when technical clarity is needed
The results spoke for themselves. Our clients renewed successfully and avoided the shock many firms experienced when insurers rejected or drastically increased premiums.
MICROSOFT 365 SECURITY HARDENING BECAME A NECESSITY
2025 confirmed what we’ve said for years: a Microsoft 365 tenant is only as secure as its configuration. Attackers increasingly targeted SaaS environments, not because Microsoft is weak, but because misconfigurations are common.
This year brought a noticeable rise in:
Unauthorized OAuth app grants
External sharing misconfigurations
Password spray attacks
Impossible travel events
MFA fatigue attacks
Misconfigured mailbox rules
Attackers bypassing security through poorly secured legacy protocols
Roark’s Ongoing Work Was Decisive:
Disabling legacy authentication
Enforcing strict conditional access policies
Reviewing sharing settings
Implementing phishing-resistant authentication where possible
Monitoring unusual login activity
Documenting tenant configurations for compliance
The businesses that trusted Roark with their Microsoft 365 environment ended the year with more secure, better controlled, and far more resilient cloud operations.
VENDOR RISK BECAME A FRONT-BURNER ISSUE
In 2025, some of the most damaging breaches came not from an attack on the business itself, but from a compromised software vendor or service provider. Small firms discovered that even if their own systems were secure, their vendors’ weaknesses could still expose them.
This is especially true in finance, legal, real estate, healthcare, and investment management, sectors where data flows across many platforms.
Roark Helped Clients Manage This By:
Reviewing vendor contracts
Ensuring vendors meet baseline security expectations
Monitoring access rights for third parties
Helping clients adopt vendor management programs that previously only large organizations used
Coordinating with vendors directly when incidents or security concerns arise
This year underscored an important truth: Security is not one company’s responsibility. It is the responsibility of every company in your technology orbit.
THE CONVERGENCE OF IT AND BUSINESS STRATEGY
More than ever, executives made technology decisions not as operational afterthoughts, but as strategic investments tied to revenue, risk, and growth. Businesses asked questions once reserved for CIOs:
What should our 2026 IT roadmap look like?
How does technology enable our next stage of growth?
Where should we invest and where should we prune?
What risks should we eliminate this year?
How do we avoid surprise costs or unexpected outages?
This shift was healthy. It meant leadership viewed technology not as overhead, but as the infrastructure that allows every other discipline to succeed.
Roark Responded By:
Building multi-year IT road maps
Helping our clients right-size their technology budgets
Creating device lifecycle plans
Consolidating vendors and cutting waste
Providing guidance that balanced risk, cost, and need
The firms that embraced this strategic mindset are entering 2026 with clarity and confidence.
THE YEAR OF THE QUIET WIN
One of the most meaningful trends of 2025 was the increasing recognition of “quiet wins” the issues that never happened. The outages avoided. The breaches prevented. The disruptions neutralized before staff ever felt them.
Clients sometimes ask, “What did Roark do this month?” Often the answer is simple: We made sure nothing happened.
Behind the scenes, Roark:
Monitored systems 24/7
Patched vulnerabilities promptly
Applied security updates that close new attack vectors
Responded to alerts in minutes, not hours
Documented activity for audits and compliance
Hardened configurations across dozens of environments
There is tremendous value in an uneventful year. It means the work is being done quietly, consistently, and correctly.
LOOKING AHEAD: What 2026 Will Demand
If 2025 was the year organizations adjusted to accelerated threat activity and regulatory focus, 2026 will be the year they mature.
Here’s what small businesses should expect:
More regulatory scrutiny. Regulators will expect documented safeguards, incident response plans, and evidence, not “good intentions.”
Higher standards from cyber insurers. Coverage will remain available only to firms with strong, well-documented controls.
Increased attacks on cloud environments. Microsoft 365, Google Workspace, and SaaS platforms will remain prime targets.
Further rise of AI-driven threats. Deepfakes, AI-crafted phishing, and automated social engineering will accelerate.
Continued pressure to simplify and secure the tech estate. Vendor consolidation and clearer configurations reduce risk and cost.
Roark is already preparing clients for this reality. With SOC 2 Type 2 and HIPAA-aligned controls, a disciplined approach to security, and a philosophy built on client ownership, accountability, and precision, our clients enter the new year on strong footing.
2025 was not an easy year for businesses navigating technology, but it was a year marked by resilience, adaptation, and real progress. Our clients embraced stronger controls, invested in better infrastructure, tightened governance, and stayed ahead of evolving threats.
Roark’s role was simple: anticipate, advise, implement, and protect.
As we look to 2026, we remain committed to delivering white-glove, risk-managed IT that helps every client operate with clarity, confidence, and control.
Since 1998, Roark Tech Services has partnered with small and mid-sized businesses to deliver disciplined, risk-managed IT that strengthens operations and reduces uncertainty.
Our belief is straightforward: your firm should own its technology, understand its risks, and have a trusted partner ensuring every system, vendor, and safeguard works as intended.
As we look toward 2026, we remain committed to guiding our clients with clarity, vigilance, and the white-glove service that keeps their businesses secure, resilient, and ready for what comes next.
If you don’t have a trusted IT partner for reliable support and strategic guidance, we’d love to help. Contact us today to discover how we can enhance your technology experience and ensure your business stays resilient.
