Editor’s note (April 2026): This article is part of Blog Herald’s editorial archive. Originally published in 2007, it has been reviewed and updated to ensure accuracy and relevance for today’s readers.
In May 2007, WordPress released version 2.2. It was, by any measure, a significant leap — widgets arrived for the first time, jQuery was bundled in, and the development team had committed to a more structured release calendar. For thousands of bloggers running their own servers, it was also the beginning of a very bad week.
One widely-read account from that period captured the chaos in real time: caching layers collapsing under load, Apache race conditions sending servers into freefall, plugins that worked individually but detonated in combination. White screens. SSH sessions that wouldn’t connect. Hours of diagnosis for problems that had no authoritative answers anywhere online. The writer summed it up plainly — he had upgraded through multiple WordPress versions before and assumed this one would be smooth. He was wrong.
That story is nearly two decades old. But the dynamics it described are still playing out today, just at a much larger scale.
The version 2.2 moment, in context
WordPress 2.2 shipped on May 16, 2007 — only a few weeks behind its publicly announced deadline, which itself was a novelty. The project had just introduced a more formal release schedule after a painfully long gap between versions 2.0 and 2.1. The intent was good: shorter cycles, more predictable shipping, less feature bloat. Version 2.1 was the first to ship with a concrete release date for the next version, and the community had come to treat those dates as a kind of promise.
The problem was that the platform had grown faster than its supporting infrastructure. Plugin authors hadn’t been given enough lead time. Server environments varied wildly — shared hosts, VPS setups, dedicated machines — and the same upgrade behaved differently on all of them. The documentation lagged behind the code. And users who ran a long roster of plugins were stepping into something nobody had fully tested: the combinatorial chaos of twenty or thirty extensions all bumping into each other on a rewritten core.
A May 2007 study found that 98% of WordPress blogs running at the time were exploitable because they were running outdated and unsupported versions of the software. That figure wasn’t just a security statistic — it was a signal that most people weren’t upgrading at all, possibly because upgrading was so painful.
The lesson that emerged slowly, and only partly, was this: the platform’s success had outpaced its upgrade experience.
What changed — and what didn’t
WordPress eventually addressed the mechanical problem. WordPress made updating the software a much easier, one-click automated process in version 2.7, released in December 2008. That single change probably did more for the platform’s security posture than any other release in its history.
What it didn’t solve was the deeper structural tension that 2007 exposed: WordPress is an open platform, which means its real-world behavior depends not just on core software, but on the entire ecosystem of themes and plugins that run on top of it. And that ecosystem is enormous and largely ungoverned.
As of 2025, WordPress powers 43.4% of all websites on the internet, commanding a 61.4% market share among content management systems — more than all other platforms combined. The official plugin repository now contains over 70,000 plugins, and the number keeps growing. That scale creates a combinatorial testing problem that no centralized team can fully solve.
The evidence is right there in recent release history. When WordPress 6.9 launched in December 2025, three of the most popular plugins on the platform broke within hours. WooCommerce checkouts stopped working. Yoast SEO’s content analysis vanished for non-English sites. Elementor’s editor refused to load entirely. Emergency patches followed within days. Anyone who had auto-updated a live site woke up to a crisis that felt, in the telling, very much like 2007.
The plugin problem hasn’t gone away
If anything, the security dimension of the plugin ecosystem has become more acute. Plugins account for 96% of WordPress vulnerabilities as of 2024. In 2024, over 1,600 plugins and themes were removed from the WordPress repository for unpatched security issues — roughly four plugins being kicked out every single day.
The WordPress Plugins Team is working on this. In 2025, the team reviewed 12,713 plugins — a 40.6% increase compared to 2024 — and plugin approvals grew by 66.2%, with 69.5% of reviewed plugins ultimately approved. Automated tooling has improved review speed and quality. Since September 2024, the Plugin Check Plugin has been integrated for automatic reviews on WordPress.org, reducing issues by 41% when approving a plugin.
But scale is relentless. Plugin submissions doubled in 2025, with the team receiving around 330 submissions per week by year’s end. The review queue grows faster than the team can process it. And the rise of AI-assisted plugin development — while genuinely democratizing — means that first-time developers are shipping code into a production ecosystem that millions of sites depend on.
The 2007 problem was a platform that had outgrown its upgrade experience. The 2025 problem is a platform that has outgrown its quality assurance capacity.
What bloggers and site owners should actually take from this
There’s a tendency in the WordPress community to treat upgrade anxiety as a beginner’s concern — something you graduate out of once you learn enough. That’s wrong. The 2007 account that kicked off this piece was written by someone with a VPS, SSH access, and multiple previous upgrades under their belt. He still got burned.
A few things remain true across nearly two decades of WordPress upgrade history:
Never auto-update a major version on a live site. Minor security patches are generally safe. Major version jumps — especially ones that touch the editor, the plugin API, or the database schema — require testing first. A staging environment isn’t optional; it’s the cost of operating a serious site.
Audit your plugins ruthlessly and regularly. The 2007 writer had around 25 active plugins and discovered that their interactions were nearly impossible to predict. That problem scales with plugin count. Experts now recommend auditing your site for any plugin that hasn’t been updated in the last six months — and removing it if no update exists.
Treat your update cadence as a strategy, not a chore. The sites that got hurt in 2007 were often the ones that had ignored updates for too long and then tried to jump multiple versions at once. The ones that get hurt today are frequently the ones that update everything the moment a major release drops. The middle path — staying current on minor releases, testing major ones — requires discipline but isn’t complicated.
WordPress in 2026 is an extraordinary platform. Over 63 million websites run on it worldwide, from personal blogs to enterprise publishing operations. Its longevity is a genuine achievement. But the hard-won lessons from a chaotic upgrade in 2007 are still valid: the platform’s openness is its greatest strength and its most persistent liability. Understanding both is what separates the sites that survive major releases from the ones that don’t.
