The company behind the disk space analyser TreeSize has irked some users by no longer offering support or updates for perpetual licenses beyond their maintenance period unless customers subscribe. Further frustration has come from JAM Software’s long-standing policy of not providing license keys or installers to TreeSize perpetual license holders after that support period ends.

Since 2025, JAM Software has been transitioning most TreeSize editions to subscription models. Today, it sells perpetual licenses only for personal use, which include 12 months of updates, support, and “downloads of older versions, and your license,” plus the option to extend the support period. TreeSize currently has “no plans to discontinue the sale of perpetual licenses for TreeSize Personal,” product manager Hendrik Christ told Ars Technica.

As perpetual-license maintenance periods expire, customers are discovering that extending support now generally requires subscribing to software they already own the right to use.

On Reddit, a user shared an email informing them that support for their perpetual license ends in September, after which they will lose access to updates and support because those “are only available in the subscription.”

Christ said that considering the “current economic conditions,” the change was “necessary to keep developing and supporting TreeSize reliably over the long term.”

One of the biggest criticisms is that JAM Software will not provide backup installation files or license keys to customers with unsupported licenses. TreeSize’s email urged the user to make backups.

“Honestly, it feels quite low to strip paying customers of the ability to simply download the installer for a software version they already paid for,” the Reddit user said.

But even before it sold TreeSize subscriptions, JAM Software didn’t permanently retain every installation file and key after a customer’s support period ended, Christ said. This is because “older software versions can contain known bugs or even security vulnerabilities,” he said, adding:

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.

The European Commission is ending an antitrust investigation into SAP after the company made numerous concessions worldwide regarding maintenance and support services for on-premises versions of its ERP solution. The Commission began its investigation in September 2025, concerned that SAP forces customers to buy its services for longer, and for more licenses, than they need.

In accepting SAP’s commitments, the Commission makes them binding on the company. SAP could still face fines if it fails to make good on its concessions over the next ten years. SAP’s promises include:

Microsoft has quietly extended its free Windows 10 Extended Security Updates (ESU) program for consumers by an additional year, allowing enrolled devices to continue receiving security updates until October 12, 2027.

The change was made without a formal announcement and instead appeared in updates to Microsoft’s Windows 10 ESU documentation and as an “Editor’s note” to a Windows Experience Blog post.

“Editor’s note – June 25, 2026 – This post has been updated to reflect that the Windows 10 Extended Security Updates (ESU) program for personal use devices is being provided for an additional year, with coverage now available through Oct. 12, 2027,” reads the updated blog post.

“This extension provides customers with more time to transition to a new Windows 11 PC while continuing to receive critical security updates.”

On October 14, 2025, Windows 10 reached the end of support, and Microsoft no longer provides technical support, feature updates, or security updates for the operating system unless you are running a Windows LTSC version.

For those who are unable to upgrade to Windows 11, Microsoft originally offered consumers an extra year of security updates if they enrolled in a free extended security updates (ESUs) program that would expire on October 12, 2026.

Enterprise customers could also enrol in the ESU program for up to three years, bringing the total cost per device to $427 over that period.

With today’s quiet update, Microsoft has now extended the free consumer ESU program to October 12, 2027, giving users an additional year to upgrade to a newer operating system.

When asked why the free ESU program was extended, Microsoft shared the following statement:

“We understand that moving to a new PC can take time. As part of our ongoing commitment to helping customers stay secure during the transition, the Windows 10 Extended Security Updates (ESU) program for personal devices is being provided for an additional year,” explained Microsoft.

“Coverage will now be available through October 12, 2027. This gives customers more time and flexibility to find the best PC for their needs while keeping them protected.”

Consumers can continue to receive extended security for free using one of these methods:

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.

Oracle customers have been warned to watch for changes in support and pricing as Larry Ellison’s company makes huge datacenter spending commitments to support its AI ambitions.

Advisors in Oracle negotiations said support levels are declining, while costs might increase as discounts disappear. Others have warned of a tougher approach to contract negotiations.

Oracle is aggressively expanding AI datacenter capacity to serve demand tied to customers and partners including OpenAI, xAI, Meta, Nvidia, and AMD. The deal for OpenAI alone is set to be worth about $300 billion over five years.

Widespread reports of layoffs affecting thousands of staff came as investor concerns grew over how Oracle would finance its AI datacenter build-out, while borrowing heavily to support the expansion.

In March, Oracle increased the estimated cost of its fiscal 2026 restructuring plan by $500 million, taking the total to as much as $2.1 billion, as observers anticipated broader job cuts.

Oracle previously raised $18 billion in debt and has since outlined plans to raise far more, as it funds datacenter investments aimed at meeting surging demand from AI model builders and enterprise customers. Ratings agency Moody’s warned of further borrowing and negative free cash flow as Oracle ramps up its AI infrastructure investment.

Nick Walter, CTO of professional consulting at commercial advisory firm House of Brick Technologies, said that there were plenty of anecdotal reports that Oracle support outcomes are getting worse, meaning slower service, less skilled help, and “more Oracle Support responses that were obviously written by AI.”

House of Brick had also seen a recent surge in customers asking for help in reducing Oracle Cloud Infrastructure (OCI) usage or help in negotiation with Oracle over long-term OCI deals, he said. “Many customers who adopted OCI in the last three to five years are suddenly finding out that their renewals are much more expensive because Oracle has eliminated or reduced enterprise discounts, and they are being forced close to public listed pay-as-you-go prices.”

Customers were also seeking help in response to pressure on Java, with audits and sales pushes and “scary-sounding threats.”

“This is not a new phenomenon but pressure continues and Java is the main front in Oracle’s war against their customer’s pocketbook,” he said.

Craig Guarente, founder and CEO of Palisade Compliance, said that Oracle was no longer simply putting pressure on customers to license Java; it was conducting official audits. “We’ve definitely seen in the last few months a return to classic Oracle auditing practices,” he said.

In 2023, Oracle changed its Java SE subscription model, shifting from a per-user or per-processor basis to per-employee. Critics called the move “predatory” as organisations that were using little Java but had a large number of employees could be hit hard by the cost increase. Later that year, research from Gartner showed that costs could be between two and five times greater under the new licensing model for using the same software.

Guarente also warned of price hikes at OCI contract renewal. “If you’re not adequately protected, then we’re getting 9 percent or 10 percent for long term lock in. It all goes back to that original purchase. You had some flexibility in there if you were thoughtful in how you negotiated those contracts. But if you signed the local standard agreement, there’s no price protection.”

Eric Guyer, founder of Oracle advisory and consulting firm Advizant, pointed out in a social media post that the margins in software support were much higher than in datacenters.

“This means the value to Oracle of your software support payments is increasing, desperately so, whereas the value to you is diminishing, and at an increasing rate. I mean this both technically via waning innovation and the more than 8 percent annual inflationary adjustments,” he said.

Customers are also concerned about the long-term impact of the job losses on their relationship with Oracle, Guyer said.

“The trend in license negotiations is only indirectly related to Oracle’s shift for now. The layoffs mean companies have lost one or more of their sales contacts. But for apps or the more strategic long-standing relationships, this means customers are wondering what this loss of institutional knowledge will mean for them. I’m not hearing customers wonder if Oracle is de-prioritising its legacy software business just yet, although I see this as an obvious outcome,” he said.