Your VPN stops working after a Windows update because the update can change network adapters, drivers or security settings that the VPN depends on. The lasting fix is to manage Windows updates and VPN configuration together, so updates are tested and the VPN settings are maintained, rather than leaving each machine to break on its own. It is one of the most common remote-working issues we resolve, and it is very preventable.
If a Windows update keeps knocking out your team’s VPN, here’s what is going on and how to stop it.
1. Why updates break the VPN
Updates sometimes reset network settings, replace a driver, or tighten a security setting the VPN client uses. The VPN then cannot connect until those settings are put right. It looks random, but the cause is usually one of a few known changes.
2. Managing updates properly
When we manage your updates, they roll out in a controlled way rather than landing unpredictably on every machine. That means fewer surprises and a chance to catch a problem before it spreads across the team.
3. Keeping the VPN client current and configured
We keep the VPN software up to date and its settings maintained, so it works with the latest Windows version. An up-to-date, correctly configured client is far less likely to break.
4. Fast fixes when it does happen
If an update does catch a machine out, our helpdesk knows exactly what to check and gets the user reconnected quickly, often remotely, so they are not left unable to work.
A real example: a quick reconnection
We supported a software company serving financial trading firms where VPN issues after Windows updates were a recurring theme until they were managed properly. When one came up, the fix was fast: the user described it as a “simple fault quickly rectified.” Managing updates and the VPN together is what turns a recurring headache into a rare one.
For most technology and trading firms, this sits within fully managed IT at about £45 to £100 per user per month, billed per user, with the security and resilience these businesses rely on built in.
Why technology and trading firms choose First Stop IT
First Stop IT has supported businesses since 2002, including software and technology companies and firms that serve financial markets. We know the systems these teams depend on: secure VPN and remote access, source control and build pipelines, virtual dev and test environments, Microsoft 365 and Teams, and the security that banks and regulators expect, from multi-factor authentication and endpoint protection to application allowlisting and email security. We work with technology and trading firms in London and across Essex and Hertfordshire. Our credentials include:
- Cyber Essentials Certified
- IASME Cyber Assurance (Gold)
- NCSC Assured Service Provider (Cyber Advisor for Cyber Essentials)
- Microsoft Partner
- Crown Commercial Service Supplier (G-Cloud)
- Quality Principles Certified
We look after more than 2,000 endpoints across 50 companies, we’ve been named a Top 50 UK MSP for three years running, and we support organisations with 10 to 100 employees across Essex, Hertfordshire and London, including Harlow and Bishop’s Stortford.
Book a free IT and cyber security review
VPN breaking after every update? Book a free IT and cyber security review with First Stop IT and we’ll put a stop to it.