The UK’s Competition and Markets Authority has opened a fresh investigation into Microsoft, this time over how the company is marketing its Microsoft 365 Personal and Family subscription plans.

A cursory glance at the probe highlights that the CMA is trying to prevent Microsoft from sneaking in Copilot and AI features as justification for recent subscription price hikes. A closer look at the investigation displays a pattern of friction Microsoft runs into with regulators regarding its subscription practices, automatic renewals, and software bundling almost every time it adjusts its services.

The CMA made the investigation public on July 29, 2026, though the case itself was opened two days earlier. According to the CMA’s case announcement, the price gap between plans is concrete. The Classic Microsoft 365 Personal plan costs £59.99 a year, compared to £84.99 a year for the Copilot-equipped version, a difference of £25 annually. The Family plan costs £79.99 a year for Classic versus £104.99 a year with Copilot bundled in.

The CMA’s announcement hinges on Microsoft’s change in January 2025, when the company automatically added new features such as Copilot to existing Microsoft 365 plans with no increase in fees for the remainder of the subscription period. Unfortunately, once the plans were up for renewal, customers who were not paying attention were re-enrolled into higher-priced plans. Customers who were paying attention could avoid the bait-and-switch by selecting a ‘Classic’ plan or cancelling during the re-enrolment period.

This price change was covered when it first happened in February 2025, and even then, Microsoft would not directly attribute the increase to Copilot in their own communications. Personal plans jumped from $6.99 to $9.99 a month in the US, and Family plans went from $9.99 to $12.99, with the Classic option only showing for existing subscribers who knew to look for it during cancellation.

CMA regulators are now examining whether Microsoft provided adequate messaging for customers to understand what changes occurred and how much more they were going to pay despite spending months using features that were initially presented as free.

As Senior Director for Consumer Protection, Hayley Fletcher puts it, “When a business changes its subscription plans, customers need clear and timely information about their options.”

According to new Lansweeper data, as many as 16.9% of Windows client devices, which equates roughly to a total of one in six overall, still runs Windows 10.

While Windows 11 now accounts for 78.8% of installs and Windows 10’s market share has fallen from about 50% in mid-2025, Lansweeper warns the migration is starting to slow down, implying the remaining Windows 10 market share could show no signs of going anywhere.

And that’s a worrying state of affairs, because the average Windows 10 device has around 3x as many active common vulnerabilities and exposures (CVEs) as a Windows 11 device (1,930 vs 652).

Additionally, around two-thirds of the active CVEs on Windows 10 are rated high or critical, and the rate of vulnerabilities known to be exploitable is around 1.7x higher than on Windows 11.

The report notes that Microsoft’s Extended Security Updates (ESU) program buys some breathing room, protecting consumers until October 2027 and paying commercial customers until October 2028.

Healthcare and pharmaceuticals (23%), consumer and retails (23%) and manufacturing (18%) are among the industries most likely to still be running Windows 10, with SMBs (21.4%) more likely to be running the outgoing OS compared with enterprises (16.6%).

Lansweeper also revealed that technical limitations aren’t necessarily to blame, with only 2.8% of the Windows 10 devices it analysed failing Windows 11’s hardware requirements.

More broadly, the report warns that nearly one-fifth (18.7%) of the entire Windows landscape it monitors runs end-of-life operating systems like Windows 7, Windows 8.1 and Windows XP.

The report concludes that, while many users have now upgraded to the latest OS, the remaining estate is smaller but disproportionately more difficult, expensive or risky to update. But with ESU programs soon running to an end, deeper considerations into leaving Windows 10 should be made.

Azul deputy CTO Simon Ritter warns that enterprise Java teams are sleepwalking towards a support cliff.

Ritter, who joined Sun Microsystems in 1996 and now works at Azul, says four long-term support versions of Java will reach end-of-support between 2029 and 2032. Java 17 goes first in 2029, followed by Java 8 in 2030, Java 21 in 2031 and Java 11 in 2032.

Writing in Infoworld, Ritter said: “Between 2029 and 2032, every currently supported long-term support (LTS) version of Java will reach end-of-support within a single three-year window.”

On paper, this looks like a neat upgrade cycle, but Ritter says the reality is a nasty collision of timelines that most enterprises have failed to forecast. Organisations still planning to modernise slowly, moving application by application and version by version, are working from a model the calendar has already mugged.

“The primary danger here is the illusion of time,” Ritter said.

Traditional modernisation plans rely on sequential upgrades and controlled pacing. Ritter argues that once every major Java version expires in the same cramped window, sequential planning collapses.

By the time that becomes obvious, companies will be forced into reactive mode. That means rushed decisions, emergency projects and the usual corporate theatre with extra Jira tickets.

For organisations planning the familiar Java 8 to Java 11 to Java 17 to Java 21 slog, a maintenance task becomes a structural problem. Enterprises with large Java estates will need to upgrade multiple applications across multiple versions simultaneously. That is needed to maintain security compliance and business continuity.

“Waiting until the late 2020s to act guarantees a modernisation process under emergency conditions,” Ritter said.

Modern Java versions still have strong backwards compatibility, but Ritter says that will not offset decades of technical debt.

Large Java environments are stuffed with unused libraries, obsolete logic, forgotten dependencies and dormant features. Much of this stuff no longer runs in production, but it still eats developer time and security oversight.

As codebases age, the drag compounds. What looks like a tidy version upgrade on a roadmap turns into a sprawling operational headache.

Ritter says most modernisation strategies assume upgrades can be sequenced and absorbed gradually. That assumption is now dangerous.

“When multiple Java versions reach end-of-support in the same narrow window, enterprises don’t face a single modernisation project; they face parallel modernisation across their entire estate,” Ritter wrote.

That moves the problem away from frameworks and into people. A typical enterprise with 100 developers cannot afford to waste chunks of its capacity maintaining dead code that delivers no business value.

Multiply that across dozens or hundreds of applications, and the bottleneck becomes obvious. Modernisation is limited by people, not magic tools. Parallel modernisation needs parallel capacity, and most organisations have not budgeted for it, he said.

Ritter says tools that analyse code in isolation cannot tell what matters in production. Without that visibility, companies default to caution and turn their timelines into risk.

“The Java modernisation crunch is a crisis of resource allocation, not a technology problem,” Ritter said.

Every hour spent maintaining obsolete code or investigating unused dependencies is an hour stolen from modernisation. When organisations face simultaneous upgrades across multiple applications, human capacity becomes the hard limit. Sequential planning needs time, while parallel modernisation needs people. Most enterprises no longer have enough of either.

Those tackling technical debt now will still have a difficult transition, but at least it will be manageable. Those who do not will face rushed choices and permanent compromises.

“By the time 2029 arrives, the window for gradual modernisation will have closed. The calendar won’t wait for us to be ready,” Ritter said.