Newsletter · October 16, 2026
A week without internet, and a server deadline that just passed
Know what you are running before it fails
This issue looks at the systems schools rely on every day, and what happens when they fail or age out. A Vermont district went a week without internet after a ransomware attack, Microsoft's final year of security updates for Windows Server 2012 has ended, and Sophos has launched a service for building a security roadmap. Every item below links to its source.
If anything here sparks a question, we are a conversation away.
Trail Ahead
A week with no internet, and teachers' personal data in a ransom demand
The Slate Valley school district in Vermont learned of its ransomware attack on September 3, when teachers came in to school and could not log in to Windows. The district was without internet and internal platforms, including the PowerSchool grading system, for a week. A group calling itself Kairos claims to hold the personal information of more than 1,500 employees, including Social Security numbers and home addresses. The district is working with an outside consultant to identify everyone affected. The FBI is investigating, and the superintendent says the FBI cautioned the district against paying. The school board has denied making any ransom payments.
Read the report at VTDigger.
Pine Cove connection: A recovery plan should center on data backup: what is copied, where the copies are kept, and whether a restore has ever been tested. After a week without internet, those answers matter. If you want a second set of eyes on yours, reach out to us.
🌲 Quick Bytes: Must-Read Articles
Security updates for Windows Server 2012 and 2012 R2 have run out
Microsoft's lifecycle pages list the final year of Extended Security Updates for Windows Server 2012 and 2012 R2 ending October 14, 2026. Mainstream support ended in 2018, and the original support window closed in October 2023.
Read the lifecycle page at Microsoft Learn
Pine Cove connection: Old servers often sit in a closet running one job, like a file share or a building system. If you are not sure whether any remain on your network, we can help you find them.
AI could change how schools test, and the article leaves out privacy
A K-12 Dive interview with Temple Lovelace of the Assessment for Good program describes AI generating new question types, scoring faster, and combining results from several systems into one profile of each learner. The article does not discuss student data protection, vendor vetting, or infrastructure.
Pine Cove connection: That gap lands on your desk. Before an assessment tool pulls data from several systems, know what it receives, where it goes, and who signed off.
🌲 Partner Pulse: News From the Brands We Build On
Sophos launches CISO Advantage, a security roadmap service
Sophos launched CISO Advantage, delivered through Sophos Fusion. It assesses an environment, maps it to frameworks including NIST CSF and CIS v8, and produces a prioritized, budget-aligned roadmap covering what to fix first and what it costs. Sophos says it is available beginning October 2026 across North America, the UK, and the rest of Europe.
Read the announcement from Sophos.
Pine Cove connection: We start with Pathfinder. From there, we can dive into Sophos Fusion as an extension of our assessment and services. Ask us how it would fit your plan.
Pine Cove Corner
This issue's stories share a starting point. A district that lost a week of internet, servers that no longer receive security updates, and a new way to build a security roadmap all begin with the same question: where do you stand today? Pathfinder 360 starts with an assessment of your current landscape and scores it across eight domains.
Schedule your Pathfinder 360 call at pinecc.com
Stay Connected Beyond the Trail Report
Our newsletter only scratches the surface of what is happening every day in the world of IT, security, and education. For the latest updates, quick insights, and resources you will not find here, follow us on LinkedIn. It is the best way to stay in the loop with Pine Cove and catch what is new before the next issue lands in your inbox.
- The Pine Cove Team
