Option 1: Upgrade to a Current Windows Server On-Premises

If your business genuinely needs on-site infrastructure — for local applications, large file workloads, or specific compliance reasons — migrating to a current version of Windows Server on new hardware is a straightforward path. You get a fresh, supported platform with a support runway of a decade or more.

Option 2: Move to the Cloud (Azure or Microsoft 365)

For many small businesses, the 2016 EOL is the perfect moment to eliminate the on-premises server entirely. File shares move to SharePoint or Azure Files, applications move to hosted platforms, and identity moves to Microsoft Entra ID. You trade hardware refreshes and server room maintenance for a predictable monthly cost — and gain built-in redundancy most small businesses could never afford on their own.

Option 3: A Hybrid Approach

Some workloads belong in the cloud; some don’t. A hybrid migration keeps a lean on-premises footprint for what truly requires it (a legacy application, a local database) while moving everything else to cloud services. This is the most common outcome for the businesses we work with — it balances cost, performance, and practicality.

There’s a persistent myth that attackers focus on large enterprises because that’s where the money is. The reality is the opposite. Small businesses are targeted precisely because they’re less defended.

• Fewer dedicated security resources — no full-time security team, often no security tools beyond basic antivirus
• Employees wear multiple hats — an office manager handling both HR and finance is a high-value target because compromising one account unlocks multiple systems
• Trusted vendor relationships — small businesses often have fewer layers of approval for payments and data requests, making fraud easier to execute
• Slower incident detection — without monitoring tools, a compromised account can go undetected for weeks or months

Attackers know this. Automated tools scan for small business domains, harvest employee names and email addresses from public sources, and generate targeted attacks at industrial scale. The idea that ‘we’re too small to be a target’ is one of the most dangerous beliefs a business owner can hold.

The industry standard for backup architecture is the 3-2-1 rule, and it applies just as much to a 10-person firm as it does to a large enterprise:

• 3 copies of your data — your primary data plus two backups
• 2 different storage media types — such as local backup plus cloud backup
• 1 copy offsite — physically or geographically separate from your primary location

The reason for redundancy is simple: different failure scenarios destroy different things. A ransomware attack can encrypt everything on your local network, including a local backup drive. A fire or flood destroys everything at your physical location. A cloud provider outage affects your offsite copy. No single backup protects against all of these — but a properly structured 3-2-1 approach does.

Local backups give you speed — restoring from a local device is dramatically faster than pulling terabytes down from the cloud. Offsite backups give you resilience — protection against physical disasters and network-based attacks that can reach anything on your local infrastructure. You need both, working in parallel, verified daily.

The subscription is only the starting point. A properly configured Microsoft 365 environment for a small business includes:

• Multi-factor authentication (MFA) enabled for every user — this alone blocks the vast majority of account compromise attempts
• Conditional access policies that control what devices and locations can access company data
• Email security configuration — SPF, DKIM, and DMARC records set correctly to prevent spoofing and improve deliverability
• OneDrive and SharePoint configured so files are actually backed up and recoverable — the default settings don’t guarantee this
• Teams set up with clear channel structure so it gets used, not abandoned
• A license audit process so you’re not paying for departed employees

Most Microsoft 365 deployments we inherit were set up quickly and never properly configured. The subscription is active, but the security baseline is weak and half the features aren’t being used.

BYOD (Bring Your Own Device) can work with the right controls in place. Without them, it’s a compliance and security liability. If employees are accessing company email, files, or systems from personal laptops and phones with no mobile device management (MDM) policy, your business data is sitting outside your control.

This becomes especially critical if you handle sensitive client data, financials, or anything subject to regulatory compliance.