The 5 Best Ways to Reduce Cyber Insurance Premiums

Let’s be completely honest with each other. You did not start your business because you are passionate about IT policies, software updates, or insurance paperwork.

You started your business to provide a great service, build a team, and make a profit.

Yet, every single year, renewal time rolls around. You open that email from your insurance broker, and your heart sinks. The questionnaire for your cyber insurance policy has doubled in length. The questions are filled with confusing jargon like “Endpoint Detection,” “MFA,” and “Patch Management.” And, inevitably, the price has gone up again.

You pay it because you know you have to. It is a necessary evil. But you are annoyed about it, because nothing ever seems to happen, and it feels like money down the drain.

What if I told you that there is a very simple, incredibly straightforward way to legally and safely reduce your cyber insurance premiums? What if I told you that one of the biggest red flags for an insurance company is something sitting right in front of you on your desk right now?

In this guide you’ll learn exactly the steps required to lower your premiums, quickly and easily. We’re going to look at the exact things insurance companies are looking for, starting with your Operating System, and how you can tick their boxes without spending a fortune.

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Does updating Windows 10 actually reduce cyber insurance premiums?

Let’s address the elephant in the room immediately. Is it true that updating my operating system from Windows 10 will reduce my cyber insurance premiums?

The Verdict: Absolutely, 100% yes.

Here is the straight-to-the-point reality of the situation. Microsoft is officially ending support for Windows 10 on October 14, 2025.

In the IT world, this is called “End of Life.” When a piece of software reaches End of Life, the creator (Microsoft) washes their hands of it. They will no longer release security updates. They will no longer fix bugs. They will no longer patch vulnerabilities.

Think of it Like Car Insurance

Think about your standard commercial vehicle insurance. If you are driving a company van with completely bald tires and you crash on the motorway, your insurance company is going to send an assessor. When that assessor sees the bald tires, they will void your policy and refuse to pay out. Why? Because you were driving an unroadworthy vehicle. You were negligent.

Cyber insurance works the exact same way.

If you are running Windows 10 after October 2025, you are driving on the digital equivalent of bald tires. Hackers know that Windows 10 will no longer be defended by Microsoft. They are actively saving up new, malicious viruses and attacks to unleash on Windows 10 computers the very second Microsoft stops protecting them.

Cyber insurers are becoming incredibly strict about this. Running an unsupported operating system is seen as a massive, preventable liability. If you apply for a new policy, or renew an old one, and admit to running Windows 10, they will either outright refuse to insure you, or they will charge you an astronomical premium to cover their risk.

Furthermore, if you suffer a breach and the insurer discovers you were running an outdated OS that you lied about on your application, they can legally refuse to pay out your claim.

By migrating to Windows 11 (or a modern macOS) right now, you demonstrate to insurers that you are actively patching vulnerabilities. This is a non-negotiable factor in keeping your business insurable and securing lower rates.

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Step-by-Step: How to Check What Version of Windows You Have

You probably don’t know off the top of your head what operating system your laptop is running – and that’s okay. It’s your job to run your business, not babysit your tech setup.

Don’t worry. It takes exactly 15 seconds to check. Here’s the step-by-step guide to finding out if you are at risk:

1. Click the ‘Start’ Button: This is the Windows logo, usually located at the bottom left or bottom centre of your screen.
2. Type the word ‘About’
3. Click ‘About your PC’: An option will pop up that says “About your PC” or “System Information.” Click here.
4. Scroll down to ‘Windows specifications’: Look for the line that says “Edition.”
5. Read the result: It will say “Windows 10 Pro,” “Windows 11 Business,” etc.

If it says Windows 10, you have a ticking clock on your hands. It is time to act.

If you have a team of 5, 10, or 50 staff members, you obviously cannot walk around to every single desk and check their computers manually. That is a terrible use of your valuable time. This is where modern business software steps in to do the heavy lifting for you. This simple 1:30 video below explains in more detail.

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How Microsoft 365 Business Licences Fix This Problem Automatically

At Yellowcom, we speak to business owners every single day who are frustrated by the constant treadmill of IT updates. You shouldn’t have to worry about whether someone in Accounts has clicked “Update Now” on their laptop.

This is where your Microsoft 365 licensing strategy becomes your best friend.

Many businesses are on the basic tiers of Microsoft 365 because it’s the best value for money option. The Microsoft 365 Business Basic licence gives you web versions of Office apps, an email mailbox, and Teams . Microsoft 365 Business Standard gives you the desktop apps you download to your PC .

But neither of these helps you with your insurance premiums on their own.

The secret weapon for small businesses is upgrading to a Microsoft 365 Business Premium licence , and pairing it with a Remote Monitoring and Management (RMM) service.

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What does that actually mean in English?

It means handing your day-to-day tech headaches to a trusted partner so you can focus on growth. Instead of relying on your staff to update their own computers, your IT partner (that’s us at Yellowcom) takes complete control of the process.

We use an enterprise-grade software that allows our IT teams to remotely monitor, manage, and fix computers and devices without needing to be in front of them. We quietly keep your laptops, PCs and systems updated and healthy. This even includes Advanced Patching, which automatically updates non-Microsoft apps like Chrome, Zoom, or Adobe Reader to keep them secure and up to date.

When your cyber insurance questionnaire asks: “Do you have a centrally managed patch management system to ensure all operating systems are up to date?”

Instead of sweating, guessing, or lying, you can confidently tick YES.

Upgrading your team to Microsoft 365 Business Premium and letting us manage your updates is an instant “easy button” for compliance. As a Microsoft Indirect Partner, Yellowcom offers local, accessible support to seamlessly transition your licences, completely handled for you with no disruption to your business.

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Why are cyber insurance premiums so high right now?

To understand how to reduce your cyber insurance premiums further, you have to understand why the insurers are panicking.

You might think, “I run a small accountancy firm/plumbing supplier/estate agency. I am not a global bank. Why would hackers target me?”

This is the biggest myth in business today. Criminals do not care about your business size or sector. In today’s digital landscape, basic security is no longer enough. Cyber threats aren’t just for global enterprises.

Here are the cold, hard facts that keep insurance underwriters awake at night:

• 42% of small businesses in the UK faced a cyber threat in 2025.
• UK SMEs face an estimated 65,000 breach attempts daily.
• The average cost of a cyber incident for a SME is around £5,000.

When massive companies get hit, it makes the news. For example, in 2025, Marks & Spencer’s suffered a ransomware attack that severely disrupted contactless payments and online orders, leading to an estimated £300 million in lost sales and recovery costs.

But small businesses are targeted because they are the low-hanging fruit. They usually have weaker defences, but their data is just as valuable to criminals. Hackers use automated robots to scan the internet 24/7, looking for easy targets. If they find an outdated Windows 10 computer on your network, they will break in, lock your customer files, and demand £5,000 in Bitcoin to give them back.

Insurance companies are paying out millions every month to cover these ransoms and recovery costs. To protect their own profits, they are demanding that you prove you are actively defending yourself before they will give you a cheap policy.

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4 More Proven Ways to Reduce Cyber Insurance Costs

Upgrading your operating system and moving to Microsoft 365 Business Premium is step one. But insurers want to see a layered approach. Firewalls and basic antivirus alone can’t keep up with today’s fast-moving threats.

If you want to negotiate the best possible rate on your insurance, you need to show them you have locked the doors, shut the windows, and installed an alarm system.

Here are three more ways to tick the boxes on that dreaded insurance questionnaire, all of which are covered under Yellowcom’s Managed IT packages:

1. Prove You Are Training Your Staff (The Human Firewall)

Your people could be your biggest vulnerability. A human element was present in roughly 70% of breaches in UK SMEs. Phishing (fake emails designed to steal passwords) is the main way cyber criminals get into UK businesses.

Insurance forms will almost always ask: “Do you provide mandatory cybersecurity training for all employees?”

Yellowcom provides a service called SATT (Security Awareness Training and Testing). This empowers your team to spot scams with engaging and customizable training modules. Before training, our baseline tests show that 40% to 70% of employees will engage with a simulated attack and are a security risk. With our monthly ongoing phishing testing and training, our mission is that you maintain a 0% click rate. Insurers love seeing this data.

2. Implement Enterprise-Grade Endpoint Protection

The days of buying a £30 antivirus CD from PC World are over. Insurers want to see “EDR” (Endpoint Detection and Response).

As part of the Yellowcom Express Bundle, we deploy Endpoint Detection and Response. This acts as a digital detective that looks for strange behaviour on your computer, investigates it, and stops attacks before they spread. We also use Advanced Antivirus, which acts as a guard dog, instantly detecting, isolating, and deleting ransomware and zero-day threats.

When you can prove to an insurer that you have 24/7 active monitoring on every single laptop in your business, your risk profile drops dramatically.

3. Bulletproof, Tested Cloud Backups

If a hacker does get in and locks your files, an insurance company doesn’t want to pay the ransom. They want you to wipe the computers and restore your files from a backup.

Therefore, they will ask: “Do you maintain isolated, regular backups of critical business data?”

Microsoft 365 does not automatically back up your data forever. If an employee deletes an entire SharePoint folder, or a hacker encrypts your emails, Microsoft cannot always get it back. As part of our User Bundle, Yellowcom provides automated cloud-to-cloud backups to ensure full Microsoft 365 data restoration in minutes.

4. Expose Your Own Weaknesses Before Hackers Do (Vulnerability Scanning & Pentesting)

If you want to secure the absolute best rates on your cyber insurance, you need to prove you are actively looking for your own weak spots. Modern insurance questionnaires will almost always ask: “Do you perform regular vulnerability scans and penetration testing?”

Most small business owners leave this blank because it sounds incredibly expensive and complicated. But think of it this way: your firewalls and antivirus are the locks on your digital doors. Vulnerability scanning and pentesting are like hiring a friendly security guard to walk around your building, jiggle the door handles, check for open windows, and make sure the alarm actually works.

Static defences like firewalls and EDR are vital, but they can’t guarantee protection against an evolving threat landscape. That is why Yellowcom fully automates these services for you, so you don’t have to hire expensive outside consultants.

• VScan: We use a tool called VScan to proactively identify open ports, outdated firmware, and other vulnerabilities. It scans your network in the background to find the digital “windows” you accidentally left open, before a criminal finds them.
• Automated Penetration Testing: Our Penetration Testing Solution continuously validates your security by mimicking the strategies of a real-world attacker to find gaps before they do. We run Automated Network Tests that perform automated simulation of internal and external attacks.

Instead of doing this just once a year to tick a box, we provide continuous monthly assessments that ensure you remain audit-ready for compliance frameworks like NIS2, DORA, and GDPR.

When the insurance broker asks for proof that your network is secure, you don’t have to guess. You will have fast, actionable reporting ready to hand straight over to them, proving your business is a safe bet.

Ready to stop guessing about your network security? Book a quick call with Yellowcom today to see how easily we can automate your vulnerability scanning and keep your insurers happy.

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The Bottom Line: Consolidate to Save Money

You might be reading this and thinking, “Okay, so I need to upgrade my Windows, buy new Microsoft licences, buy backup software, buy training software, and buy new antivirus. This sounds more expensive than just paying the higher insurance premium!”

If you try to buy all of these things separately from different vendors, you are absolutely right. It will be a logistical nightmare and a massive drain on your cash flow.

That is the entire point of Managed IT.

Managed IT means handing your day-to-day tech headaches to a trusted partner so you can focus on growth. It’s a subscription partnership where real engineers monitor, secure, and support your users and devices 24/7.

At Yellowcom, we believe in One Partner. You can simplify your operations by consolidating your IT support, Microsoft 365 licences, phone systems, and cybersecurity under one expert provider. One bill, one team, one less headache.

Our packages, designed for businesses from 1 to 300 users, bundle all of these insurance-pleasing security tools into one predictable monthly cost . Budget accurately for your security spend with consistent monthly pricing.

The cost of keeping staff trained and vigilant, and keeping your devices updated, is always significantly less than the cost of just one security incident.

Are you ready to stop overpaying for Cyber Insurance? Take the first step towards robust support and let Yellowcom help your business achieve its technology goals. Stop worrying about outdated Windows software and start focusing on your business.

Book a Free IT & Microsoft 365 Health Check with Yellowcom Today

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Useful Links

Microsoft: Windows 10 End of Support Lifecycle (https://www.microsoft.com/en-gb/windows/end-of-support): Official details directly from Microsoft regarding the October 2025 deadline and why upgrading is a critical necessity for your business.

NCSC: Small Business Cyber Security Guide (https://www.ncsc.gov.uk/collection/small-business-guide): The UK Government’s official, jargon-free guide covering the absolute basics of cybersecurity, designed specifically for small and medium-sized business owners.

Cyber Essentials Certification Overview (https://www.ncsc.gov.uk/cyberessentials/overview): Learn about the UK government-backed scheme that protects against common cyber attacks. Holding this certification is a proven way to further reduce insurance premiums.

Book a Free Yellowcom IT Audit (https://www.yellowcom.co.uk): Let our local experts review your Microsoft 365 licences and cyber setup to ensure you are fully protected, compliant, and ready for your insurance renewal.