Many organisations are running workloads on Windows Server 2016 without realising that it has now entered its End of Life (EoL) phase. When an operating system reaches EoL, it stops receiving security updates, which exposes businesses to significant cybersecurity risks.
At the same time, email-based attacks — especially phishing — continue to rise. This makes security awareness training and modern phishing-detection platforms essential parts of your defence strategy.
In this article, we break down what Server 2016 EoL really means, the risks it introduces, and why now is the perfect time to implement phishing-resilience tools like Ironscales.
Windows Server 2016 Has Reached End of Life — What Does This Mean?
Windows Server 2016 entered its Extended Security Update (ESU) end date in January 2024. However, Microsoft does offer paid ESU coverage until January 2027 for organisations that require more time to migrate. If your organisation has not subscribed to ESU or has reached the end of that period, you will no longer receive:
- Security patches
- Vulnerability fixes
- Performance improvements
- Technical support from Microsoft
Operational Risks of Running an EoL Server
- Growing susceptibility to ransomware
- Compliance issues (ISO, SOC 2, HIPAA, GDPR)
- Increased downtime from unpatched exploits
- Reduced compatibility with modern software and cloud services
- Hardware running Server 2016 is likely around nine years old at this point, making it significantly less reliable and more prone to failure
EoL systems are one of the top targets for threat actors because vulnerabilities remain open indefinitely. That is why EoL servers increase the likelihood of phishing success.
Why EoL Servers Increase the Likelihood of Phishing Success
Phishing is still the number one way attackers breach networks — and outdated infrastructure makes phishing even more effective.
Here’s why:
- Unpatched servers can’t detect or mitigate modern attack techniques.
- Attackers often use phishing to gain initial access, then exploit known server vulnerabilities.
- Weak authentication and old protocols in EoL systems increase damage severity once an attacker gets in.
- Legacy servers are often tied to legacy user behaviours — outdated security habits, less MFA, weaker policies.
This is why upgrading or securing Server 2016 must go hand-in-hand with improving your human layer of defence.
Strengthening the Human Firewall: Phishing Awareness Training with Ironscales
Modern phishing attacks are increasingly AI-generated, hyper-personalised, and harder to recognise.
This is where Ironscales becomes a critical part of your defensive stack.
What Ironscales Provides
- AI-powered email threat detection
- Real-time alerts and automated remediation
- Phishing simulation campaigns
- Ongoing user behavior analytics
- A mobile app for rapid reporting
Why Ironscales Matters Right Now
With Server 2016 EoL increasing your risk exposure, training users to spot malicious emails becomes a crucial compensating control. Even if you are not ready to migrate your server, improving user awareness immediately reduces attack success rates.
Recommended Actions for Organisations Still Running Server 2016
Short-term (0–30 days)
- Deploy phishing awareness training with Ironscales
- Enforce MFA across all accounts
- Strengthen email filtering rules
- Review admin accounts and privilege levels
Medium-term (30–90 days)
- Plan your migration to Windows Server 2022 or Windows Server 2025
- Patch all remaining on-prem systems
- Conduct a cybersecurity gap assessment
- Update backup and disaster recovery processes
Long-term (90+ days)
- Complete the migration from Server 2016
- Modernize your identity access management
- Implement zero-trust principles
Server 2016 End of Life is more than an IT lifecycle milestone — it’s a security turning point. As vulnerabilities grow and attackers leverage increasingly sophisticated phishing techniques, companies must combine infrastructure upgrades with stronger user-focused defences. Thus, platforms like Ironscales help your organisation reduce risk immediately by training employees to recognise and report threats — a crucial layer of protection while you transition away from legacy systems.
If you’re still running Windows Server 2016, now is the time to act.
Are you in the Shropshire area and you want to make sure your business is secure? Reach out to us and we will make sure we keep you safe.
