IT Support That Just Works, for Long Island & NYC Businesses

If your organization is still running Windows Server 2016, now is the time to plan what comes next.

According to Microsoft’s product lifecycle, Windows Server 2016 extended support ends January 12, 2027. After that date, it no longer receives the regular security updates, bug fixes and technical support of the standard lifecycle. Microsoft has also announced Extended Security Updates (ESUs) as a temporary option for organizations that need more time, while recommending a move to a current Windows Server release or another supported platform.

For many small and midsize businesses, though, Windows Server 2016 end of support shouldn’t automatically mean buying another physical server. It’s a chance to ask a more important question.

Do We Still Need This Server?

Many Windows Server 2016 systems were originally installed for:

• Shared company files and mapped drives
• Active Directory
• Business applications
• QuickBooks, Sage or other accounting software
• Print services
• Backup
• Remote access
• Application databases

Some of those workloads may still need a server. Others may not. If your server’s main job today is giving employees access to shared Word documents, Excel spreadsheets, PDFs, project files and department folders, moving those files to Microsoft SharePoint and OneDrive may be a better long-term strategy than replacing it with another file server.

Why Consider SharePoint Instead of Another File Server?

Traditional file servers were built for employees working in the office and opening files from mapped drives like F:\Company Files or J:\Job Files. Today, people need information from the office, home, job sites, client locations and phones.

Access Files From Anywhere

Instead of connecting back to the office server, authorized users can securely reach SharePoint documents through Microsoft 365. For organizations with multiple offices, remote staff or field workers, that removes a major dependency on the physical office.

Better Collaboration

With SharePoint and Microsoft 365, teams can work on documents together instead of creating Proposal-Final.docx, Proposal-Final-v2.docx and Proposal-Final-REALLY-FINAL.docx. That means fewer duplicate files and clearer visibility into what’s current.

Less Physical Infrastructure

An on-premises file server comes with server hardware, Windows Server licensing, storage, backup, UPS equipment, warranties, server-room space, remote access and ongoing maintenance. Moving the right file workloads to SharePoint can reduce that burden. It doesn’t mean eliminating every server. It means checking whether each workload still belongs there.

SharePoint Is Not Simply a File Server in the Cloud

A successful SharePoint migration isn’t copying every mapped drive into one giant document library. TCI recommends reviewing four things first:

• Folder structure: years of use leave duplicate data, obsolete files and folders nested ten levels deep. Migration is the time to clean up.
• Permissions: who needs access? What’s company-wide, departmental or confidential? Are old permissions still appropriate? Those answers become a cleaner SharePoint security model.
• Data: not everything should move. Identify obsolete, duplicated and temporary files first.
• Architecture: instead of mirroring the old server, design SharePoint around how your organization works: company resources, accounting, HR, operations, projects, sales and management.

But Not Everything Belongs in SharePoint

SQL databases, line-of-business applications, some accounting and legacy ERP systems, application servers and software that requires traditional mapped-drive (SMB) access may still need Windows Server, Azure or another supported platform. That’s why the first step should be a Windows Server 2016 assessment, not just a file migration. Microsoft itself recommends inventorying server roles, applications, users, certificates, DNS, remote access, backups and integrations before migrating.

What Are Your Windows Server 2016 Options?

There isn’t one right answer for every organization:

Option 1: Upgrade to Windows Server 2025

If you still need on-premises infrastructure, supported workloads can move to Windows Server 2025, Microsoft’s current release.

Option 2: Move Workloads to Microsoft Azure

Some server workloads fit better in Azure than on new hardware, especially if you want to reduce on-site equipment or need cloud availability.

Option 3: Move File Services to SharePoint and OneDrive

Ideal when your server mainly stores and shares documents. SharePoint becomes home for shared organizational and departmental information; OneDrive is for each person’s working files.

Option 4: Use a Hybrid Approach

Often the right answer: company files in SharePoint, personal files in OneDrive, identities in Microsoft Entra ID, legacy apps on Windows Server 2025 or Azure, and modern cloud or immutable backups. The goal isn’t to be “100% cloud.” It’s putting each workload where it makes the most sense.

Option 5: Extended Security Updates

If an application can’t move before January 12, 2027, ESUs can provide critical security updates for a limited time. They’re a bridge, not a modernization strategy: no new features, and not a long-term replacement for a supported platform.

Don’t Wait Until January 2027

A server migration isn’t something to plan the week before support ends. Start by answering:

1. Which Windows Server 2016 systems are still running?
2. What roles does each server perform?
3. Which applications depend on it?
4. What data is stored there, and who has access?
5. What can move to SharePoint or OneDrive?
6. What still requires Windows Server?
7. Should remaining workloads stay on-premises or move to Azure?
8. How is the environment backed up today?
9. What needs testing before the old server can be retired?

The earlier you answer these, the more options you have.

Turn End of Support Into an Opportunity to Modernize

Windows Server 2016 end of support doesn’t have to be another forced upgrade. It’s a chance to check whether decisions made five, eight or ten years ago still make sense. A business that once needed several servers may now run on Microsoft 365 + SharePoint + OneDrive + Entra ID + Azure + modern cybersecurity + cloud backup. Others will still need on-premises servers, and that’s perfectly reasonable. What matters is deciding based on today’s requirements, not replacing a server just because that’s what happened last time.

How TCI Technologies Can Help

TCI helps Long Island and NYC organizations prepare for Windows Server 2016 end of support with a practical modernization plan, including server discovery and assessment, application and workload review, file-server assessment, SharePoint migration planning, permissions design, OneDrive migration, Microsoft 365 and Entra ID planning, Windows Server 2025 and Azure migration, backup and disaster recovery, cybersecurity modernization and legacy server retirement. Already have an IT team? We can support the project through co-managed IT.

Still Running Windows Server 2016?

January 12, 2027 is approaching. Don’t wait until end of support to discover what depends on your server. Schedule a Windows Server 2016 & modernization assessment with TCI Technologies, or call us at (516) 484-5151.

Microsoft 365 Copilot can save your team hours every week, drafting emails, recapping meetings, summarizing documents and finding information across Microsoft 365. Turning it on is easy. Turning it on safely takes some preparation.

Here’s what Microsoft 365 Copilot readiness means, what to check before rollout, and how Long Island and NYC businesses can get it right the first time.

Why Copilot Readiness Matters

Copilot Sees What Users Can See

Copilot works within each person’s existing access. If a salary spreadsheet or HR folder is shared too widely, Copilot can summarize it for anyone who has access, even if they never knew it was there.

Old Sharing Links Add Up

Years of “anyone with the link” shares, forgotten guest accounts and overly broad team sites are common, and Copilot makes all of it much easier to find.

Licenses Are an Investment

Microsoft 365 Copilot is a paid add-on for each user, so it pays to start with the people and roles who will get the most value from it.

Results Depend on Adoption

Without training and clear guidelines, many people try Copilot once and give up. A planned rollout turns curiosity into real time savings.

The Microsoft 365 Copilot Readiness Checklist

Before rolling Copilot out broadly, review these areas:

A Practical Four-Step Path to Copilot

1. Review Access & Sharing

Review who can access what across SharePoint, OneDrive and Teams, and identify overshared files, old sharing links and unused guest accounts.

2. Clean Up & Tighten

Fix permissions, remove outdated access and tidy up sites, so sensitive information stays with the right people before Copilot goes live.

3. License & Pilot

Decide who gets Copilot first, handle the licensing, and start with a small pilot group to prove the value before a wider rollout.

4. Train & Set Guidelines

Provide hands-on training plus a simple AI usage policy, so your team knows how to get good results and what information to keep out of prompts. After rollout, ongoing AI governance keeps users, licenses, security settings and policies on track.

Common Questions About Copilot Readiness

Do we really need to prepare before turning on Copilot?

We strongly recommend it. Copilot doesn’t change who can see what, but it makes anything people can already access far easier to find. Cleaning up first is the simplest way to avoid surprises.

How long does getting ready take?

It depends on how many users, sites and files you have, and how much tidying is needed. An initial review produces a clear plan and timeline before any work begins.

Which Microsoft 365 plans work with Copilot?

Microsoft 365 Copilot is available as an add-on for most Microsoft 365 business and enterprise plans. Licensing changes often, so check your current plans before buying.

Is our company data used to train Microsoft’s AI?

Microsoft states that your prompts and business data in Microsoft 365 Copilot aren’t used to train its underlying AI models, and that Copilot respects your existing security and compliance settings.

See It in Action

Read how a law firm rolled out Copilot safely: How a 50-Person Law Firm Put Microsoft 365 Copilot to Work, Safely.

Is Your Organization Ready for Copilot?

Find out in minutes with our free Microsoft 365 & AI Readiness Assessment. Ready to move forward? See how TCI helps with Microsoft 365 Copilot consulting, readiness, deployment and training, or call us at (516) 484-5151.