Technically, yes, but it’s not recommended. After October 14, 2025, Microsoft will cease releasing security updates, leaving systems vulnerable to emerging threats and cybercriminals targeting known issues.

How do I know if I am still running Windows 10?

To check if you are still running Windows 10:

1. Click the Start button (Windows icon in the bottom-left corner of your screen).
2. Type "About your PC" and press Enter.
3. In the window that opens, scroll to the "Windows specifications" section.
4. Look for the Edition entry — if it says "Windows 10", you are still running Windows 10.

You’ll also see the version and build number listed, which can help identify how up-to-date your installation is.

How do I know if my computer can be upgraded?

To check if your computer is compatible with Windows 11, use the official PC Health Check tool from Microsoft:

1. Download the PC Health Check tool from the Microsoft website.
2. Install and run the tool.
3. Click “Check now” under the Windows 11 section.
4. The tool will analyse your system and let you know if it meets the requirements for Windows 11.

What are the risks of not upgrading?

Risks include increased exposure to phishing, ransomware, and malware attacks, software compatibility problems with newer applications, compliance issues in industries like healthcare, finance, and law, and potential insurance claim rejections due to unsupported systems.

Will data be lost during the upgrade?

Proper backups ensure that documents, emails, bookmarks, printer settings, and other data can be preserved during an upgrade.

What if some applications aren’t compatible with Windows 11?

Compatibility checks should be conducted for essential tools prior to upgrading. Necessary adjustments or replacements may need to be considered.

How much downtime is typical?

Upgrades generally take 1–2 hours per device. Scheduling should aim to minimise disruption to daily operations.

What happens if the upgrade is postponed until September or October?

Delaying could lead to industry-wide scheduling bottlenecks, increased costs, and last-minute complications as the deadline approaches.

Can the upgrade be carried out internally?

While possible, upgrading business computers involves more than simply clicking “update.” It requires backing up critical data, confirming software compatibility, reconfiguring printers, accounts, shared drives, and more. Proper planning and execution are necessary to avoid mistakes or downtime.

📉 Cyber Insurance Implications

Most cyber insurance policies include specific language requiring that the systems under coverage are actively supported by their vendors, regularly patched, and maintained to a “reasonable security standard.”

After October 14, Windows 10 will no longer receive security updates from Microsoft. From an insurance perspective, that places any Windows 10 device firmly in “unsupported” territory.

In the event of a breach, ransomware attack, or data loss incident involving one of those machines, or even if it’s simply part of the affected network, insurers may:

• Deny the claim outright
• Reduce the payout
• Or reject liability for failing to meet basic security obligations

We’re already seeing more insurers asking businesses to attest that they are not running unsupported software. Others may review systems during underwriting or renewal. Either way, unsupported endpoints present a documented claims risk.

If you hold cyber insurance — or plan to apply — this is a critical factor to address proactively.

🧾 Regulatory & Contractual Compliance Risks

For businesses that handle sensitive data — such as customer records, payment info, intellectual property, or regulated communications — continuing to run Windows 10 can pose compliance risks, even in the absence of an actual security incident.

Most modern data protection frameworks (including GDPR, HIPAA, PCI DSS, and ISO 27001) share a core requirement: that organizations take “reasonable steps” to protect the data they hold.

Using systems known to be unsupported after a public end-of-life date may not meet that threshold.

In the event of an audit, internal review, or legal dispute, the presence of unsupported operating systems could be cited as a failure of due diligence, particularly if those systems play a role in the organisation’s core operations or data handling workflows.

In some industries, client contracts may also require that IT systems be kept current, patched, and supported, making this an issue of legal, not just technical, compliance.

If you need assistance navigating these challenges or ensuring your systems and processes are compliant, please don’t hesitate to get in touch. We're here to help you protect your business and meet your obligations with confidence.