cb20 vCIO Quarterly Insights
September 2026 Edition
Technology Changes, Security Trends, and Strategic Planning for the Months Ahead
From Microsoft’s upcoming Outlook transition to the rapid adoption of AI and evolving cybersecurity threats, cb20’s vCIOs share their take on the IT news and trends worth paying attention to — and what they could mean for your business in the months ahead.
FEATURED STORY: The New Outlook Is Coming: Is Your Business Ready?
Microsoft is continuing its transition to the New Outlook experience for Windows users, and organizations should begin preparing now. While Outlook Classic remains available today and will continue to be supported through at least 2029, Microsoft’s transition timeline is already underway.
Outlook Transition Timeline
- Current Phase: Opt-In – Users can test the New Outlook today and switch back to Classic Outlook if needed.
- Opt-Out Phase: Began April 2026 – New Outlook becomes the default experience.
- Mandatory Cutover Phase: Microsoft has not announced a start date yet but has committed to giving at least 12 months notice before implementation – Users will no longer be able to switch back to Classic Outlook, and new Microsoft 365 deployments will include New Outlook by default.
Why This Matters
For many organizations, Outlook is more than just email. It connects with critical business applications such as:
- CRM systems
- Document management platforms
- Scheduling and workflow tools
- Industry-specific applications
- Productivity add-ins
The biggest concern isn’t just being familiar with the new interface, but also ensuring that any third party tools businesses use with Outlook are properly configured with the new Outlook to work as expected without interruption or error.
What Organizations Should Do Now
- Inventory Outlook add-ins currently in use
- Identify business-critical Outlook integrations
- Test workflows within the New Outlook experience
- Prepare employees for upcoming changes and familiarize them with the new interface
- Develop a transition plan before migration becomes mandatory
cb20’s vCIO Perspective
Organizations that plan early often avoid costly disruptions later. The Outlook transition presents an opportunity to review business processes, evaluate application dependencies, and ensure a smooth user experience before Microsoft makes the move mandatory.
STRATEGIC TECHNOLOGY SPOTLIGHT: AI Adoption Starts with Data Governance
Artificial intelligence is rapidly becoming part of everyday business operations. Even industries that have traditionally been cautious about technology adoption are actively exploring AI tools and workflows. The biggest concern we’re hearing isn’t whether organizations want to use AI; it’s whether their data is protected. Many business leaders are asking:
- Is our company data secure?
- What information can employees safely use with AI tools?
- How do we maintain control over sensitive information?
Understanding the Difference
Many licensed business AI solutions, such as Microsoft Copilot, include enterprise-grade security controls and do not use customer data to train public AI models. However, successful AI adoption requires more than selecting the right tool. Organizations should understand:
- Where business data resides
- Who has access to sensitive information
- How data is classified and managed
- Whether governance policies are in place
Questions to Consider
- Do you know where your critical business data is stored?
- Are access permissions regularly reviewed?
- Is your organization prepared to adopt AI safely and responsibly?
For many organizations, AI readiness begins with stronger data governance practices.
♦ Can Your Current Data Governance Support AI?
Before adopting AI tools like Microsoft Copilot, it’s important to understand where your data lives, who has access to it, and whether sensitive information is properly protected. Our team can help evaluate your Microsoft 365 environment, strengthen data governance, and prepare your organization for secure AI adoption.
Schedule a Microsoft 365 AI Security Assessment
CYBER INSURANCE & SECURITY POSTURE: Are Your Cybersecurity Controls Ready for Renewal Season?
Cyber insurance carriers continue to raise expectations around security controls and documentation. Many organizations are required to attest that certain protections are in place, including:
- Multi-factor authentication
- Endpoint protection
- Backup and recovery capabilities
- Security monitoring
- Access controls
- Remote Access security configuration
Before renewing your policy, it’s important to verify that your security controls align with what is being reported to your insurance provider.
Why It Matters
An accurate security assessment can help:
- Reduce risk exposure
- Strengthen overall security posture
- Improve insurability
- Potentially impact premium costs
A proactive review today can help avoid difficult conversations during renewal season.
♦ Are You Prepared for Your Next Cyber Insurance Renewal?
Our cybersecurity specialists can review your current security controls, identify potential gaps, and help ensure your organization is better prepared before completing your insurance questionnaire.
Learn more about our Cybersecurity Solutions
SECURITY WATCH: AI-Powered Vishing
Cybercriminals are increasingly using artificial intelligence to replicate a person’s voice with only a short audio sample. Similarly named to phishing, vishing scams use replicated voices and social engineering to create highly convincing scam calls that sound like a friend, family member, or coworker urgently asking for help or sensitive information. Examples include:
- Family emergency scams
- Executive impersonation attempts
- Fraudulent payment requests
- Urgent wire transfer requests
How to Protect Yourself
If you receive an urgent plea over the phone, always use extreme caution and never share personal or sensitive information over the phone without verifying the caller’s identity:
- Create a family or company verification phrase. If a caller requests urgent action, use this private passcode to help verify their identity before proceeding
- Simply hang up and call back the person directly on their verified phone number.
As cyber threats evolve, security awareness is becoming just as important as technology controls.
♦ Could Your Employees Spot an AI Voice Scam?
Technology alone can’t stop every cyber threat. We help organizations strengthen their security posture through layered defenses, user awareness, and practical cybersecurity best practices.
Schedule a complimentary cybersecurity assessment
COMPANY NEWS: cb20 Transitions to a Managed Security Services Provider
cb20 recently announced its transition from a Managed Services Provider (MSP) to a Managed Security Services Provider (MSSP). The move formalizes the company’s security-first strategy by integrating cybersecurity into every layer of technology management to help organizations reduce risk, strengthen operational resilience, and preserve business continuity.
“Too many providers still sell the illusion of security,” said Chris Pickett, President & CEO of cb20. “They deploy tools, check boxes, and move on. That isn’t enough. What organizations need are partners who understand their business, anticipate evolving threats, and build security into every decision – not just after something goes wrong.”
CLIENT SUCCESS SPOTLIGHT: Cooney & Tyner Orthodontics
Cloud Adoption Delivers Measurable Business Benefits
Organizations continue to see significant operational improvements through well-planned cloud migrations. One recent client transition with Cooney & Tyner Orthodontics demonstrated several measurable benefits, including improved system stability, fewer support requests, increased resiliency, and enhanced security capabilities. Beyond flexibility and accessibility, cloud adoption can simplify technology management while reducing long-term operational burdens. As organizations evaluate future technology investments, cloud modernization remains a powerful strategy for improving both performance and security.
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Questions or Feedback?
If you would like to learn more about any of these topics or have feedback, we'd love to hear from you. Feel free to email info@cb20.com or contact us.