Jonathan Desrosiers, a principal software engineer at Bluehost and a long-time WordPress contributor and Core committer, joined the Jukebox Podcast to discuss making WordPress releases more meaningful, connecting releases to flagship community events, and rebuilding contributor and local-community engagement post-COVID.

Background and sponsorship
Jonathan has been using WordPress for nearly two decades, contributing for over a decade, and serving as a Core committer for almost eight years. At Bluehost he’s sponsored through Five for the Future, spending much of his time improving contributor experience, automating processes, and removing barriers so more people can participate.

Releases as community moments
A recent instance where a major release coincided with State of the Word in San Francisco created a theatrical “big red button” moment—publishing a release live at an event. The idea is not merely PR; it recognizes that community is the heart of open source. Combining a release with an in-person flagship event can create shared moments of celebration, increase visibility, and invite more people to feel part of something larger.

Will synchronized releases continue?
The plan for 2026 proposes pairing releases with flagship WordCamps (e.g., WordCamp Asia, WordCamp US) and State of the Word, but Jonathan emphasizes this is experimental. Event dates are determined by local organizers who must balance budgets, holidays, travel, weather, venue availability—so releases can’t dictate event timing. Global calendars add complexity: many regions observe religious and national holidays that affect contributor availability (e.g., Thanksgiving, Hanukkah, Christmas, New Year), and December often becomes a low-productivity period.

Logistics and global coverage
Synchronized releases demand thinking about global coverage. Release squads should include contributors across time zones so someone is available to respond throughout the cycle and if event-day connectivity or logistics fail. Traveling contributors may be present at events, but release teams need members who are remote and available to handle issues. The goal is inclusivity: in-person attendance shouldn’t be required to participate.

Making releases more visible and useful
Jonathan and Nathan discussed making release moments more like TV seasons or product launches—building anticipation and awareness. The current about page and release microsite only reach users who manually update or visit those pages. Jonathan suggested exploring more proactive ways to highlight upcoming features in dashboards (e.g., widgets linking to Learn WordPress), enabling early opt-in testing, and nudging users to try new features.

Feature-branch model and release cadence
Jonathan favors a model where significant features can be developed and tested on separate branches so they can be released independently when ready. This can help users opt into specific features earlier and create clearer testing and feedback paths. However, the complexity of interdependent packages (especially in the block editor) and WordPress’s long-standing backward-compatibility commitments make fine-grained, frequent feature releases challenging. The team needs better automation and architectural compartmentalization before widespread feature-by-feature releases become feasible.

Adoption and auto-updates
Data Jonathan examined showed strong, accelerating adoption for recent major releases: across the last 10 major releases, each passed a 35% installation threshold within two days or less. WordPress 6.9 reached 50% of sites in 10 days—four days faster than 6.8—and is approaching 65%. This suggests users are increasingly confident in auto-updates for major versions and that the project is shipping stable releases. Faster adoption supports thinking about how to better communicate new features and invite testing.

Rebuilding community and contributor pipelines
Both hosts observed strain in local Meetups and WordCamp participation since COVID. Contributor pipelines were disrupted: many organizers and leaders moved on or burned out, breaking the mentorship and leadership handoff cycle. Geographic variation exists; APAC communities appear strong and growing, while some US and UK meetups face difficulties in finding speakers and attendees. Rebuilding requires proving community value and offering clear pathways for newcomers.

Education, mentorship, and WP Credits
Initiatives aimed at education and onboarding—WP Credits, mentorship programs, contributor days, campus outreach—seek to attract new contributors, especially younger people. Jonathan noted successful contributor mentorship programs that produced contributors who returned to mentor later and moved into team lead or release roles. However, outreach must be paired with activation: when people are introduced to open source, the project must be ready to support, mentor, and provide clear, meaningful tasks so new contributors can continue after an introductory event.

Using events to onboard and retain contributors
Synchronous release events and contributor days provide opportunities to pilot better onboarding and retention practices. For example, packaging a release candidate as a testable ZIP for onsite testers can give newcomers a concrete way to help (report PHP versions, installation methods, and issues). Making this testing effort more meaningful—ensuring reports are collected, triaged, and visible—can turn a one-day activity into a continuing contributor journey.

Attracting younger contributors and the role of excitement
Younger generations have different expectations: instant, highly visual, and personally empowering tools. To attract them, WordPress must be relevant, exciting, and offer clear value—both as a learning platform and a career path. That may mean rethinking Meetups and WordCamps formats, improving learning materials, and leveraging new tooling to reduce friction and amplify what’s fun about building on WordPress.

AI, openness, and empowerment
Jonathan sees AI as a powerful enabler for learning and personal empowerment: models can digest large amounts of material and present it tailored to how an individual learns. AI lowers the barrier to experimentation, enabling people who previously relied on professionals to try building and solving problems themselves. This could revive interest in owning websites and open platforms (e.g., blogging, RSS, Fediverse) as people grow wary of closed silos and platform instability.

Challenges remain: AI can produce quick but brittle solutions, and scaling those projects securely and sustainably requires expertise. Nonetheless, AI can help show the value of open platforms by making building more accessible and immediate.

Final thoughts
Jonathan advocates continuing to experiment with synchronized releases and leveraging flagship events to create meaningful community moments while recognizing logistical and architectural constraints. Rebuilding local communities will take education, mentorship, clearer contributor pathways, and making WordPress and its events appealing to newer generations—possibly by leaning into AI-enabled empowerment and by highlighting the enduring benefits of openness.

Find Jonathan at jonathandesrosiers.com, on the wordpress.org Slack, or as desrosej across social platforms.

Nathan Wrigley hosts Jonathan Desrosiers, a principal software engineer at Bluehost and a long-time WordPress contributor and Core committer sponsored through Five for the Future. They discuss syncing WordPress releases with flagship community events, improving contributor experience, and rebuilding community engagement post-COVID.

Jonathan explains the idea to align major releases with events like WordCamp Asia, WordCamp Europe, WordCamp US, and State of the Word. The concept began somewhat serendipitously when a release coincided with State of the Word and was published live at the event. The goal is to create celebratory community moments—combining the technical milestone of a release with the human element of gatherings to make contributions and achievements more visible and meaningful.

Logistics and scheduling are major challenges. Event dates are determined by many factors—budgets, venue availability, regional holidays, and travel considerations—and can’t be planned around the release cadence. Conversely, the release schedule must consider global calendars (religious holidays, national breaks) that affect contributor availability. The teams try to ensure “global coverage” by assembling release squads with members across time zones so someone is available to handle issues even when parts of the world are offline.

Jonathan and Nathan discuss the theatrical aspect of synchronized releases—the “big red button” feel—and whether that fanfare can help raise awareness. Jonathan wants releases to be more visible without turning them into pure marketing: it’s about celebrating community work and creating moments that draw people in. He also notes the benefit of frequent, smaller releases in principle—faster feedback and less delay between contribution and deployment—while recognizing the realities of WordPress’s size and backward-compatibility commitments.

Awareness and onboarding are important themes. Many users don’t notice releases because auto-updates are seamless, which is a sign of quality but also means people miss learning about new features. Jonathan suggests better ways to surface new capabilities—dashboard widgets, Learn WordPress links, or pre-release communication—to encourage testing and involvement. He describes a feature-branch model where discrete features can be surfaced and tested independently, though he acknowledges technical and architectural complexity given how interconnected parts of the editor are.

Data shows adoption is accelerating: recent major releases reach large percentages of WordPress sites faster than earlier versions, indicating confidence in updates and successful auto-update behavior. For example, WordPress 6.9 reached 50% of sites in ten days, faster than prior releases.

The conversation turns to community health. Both agree COVID caused a lasting disruption: many Meetup and WordCamp leaders stepped away, and the usual mentorship and succession pipelines broke. Attendance at Meetups and regional WordCamps has fallen in some places, and rebuilding requires different strategies in different regions. APAC shows strong growth and newer communities, while the US and Europe face challenges in re-energizing local groups.

Efforts to rebuild include education, mentorship, WP Credits, and contributor mentorship programs that have shown success by turning mentees into mentors and leaders. Jonathan emphasizes that it’s not enough to attract people; projects must provide clear pathways, support, and meaningful tasks so newcomers can continue contributing after initial events like Contributor Day. Release parties and in-person testing during events can be valuable pilot programs for onboarding and process experiments.

Nathan and Jonathan discuss engaging younger generations who grew up with closed platforms and social media. Convincing them of open source’s value and getting them involved means making the experience relevant, exciting, and practical—showing career pathways and ways to build real products and services. Education initiatives targeting schools and universities are promising but must be paired with activation and support so newly interested contributors don’t stagnate.

AI is acknowledged as a major factor shaping the future. Jonathan sees AI as empowering and enabling learning: it can digest and summarize information, help people try building things without deep technical knowledge, and lower the barrier to experimentation. This empowerment could drive a resurgence in personal websites, blogging, and using open platforms rather than relying solely on walled gardens. However, he cautions that AI also creates a wave of low-quality outputs and that scaling robust, secure, and accessible solutions will still require skilled contributors.

They agree AI can make people more likely to try things themselves—both online (building sites or apps) and offline (DIY tasks)—and may renew interest in owning and controlling digital presence. WordPress can benefit from this if it provides the right tools, documentation, and welcoming contributor paths.

In closing, Jonathan reiterates his focus on contributor experience: automating processes, clarifying tasks, mentorship, and creating opportunities for people to see their work reach production. He invites listeners to participate in events and contributor days and points to his website (jonathandesrosiers.com) and the WordPress.org Slack for contact.

Nathan hopes the combination of synchronized releases, educational initiatives, Meetups, and AI-driven empowerment will revitalize community involvement so WordPress remains relevant and vibrant in the next decade.

Welcome to the Jukebox Podcast from WP Tavern. I’m Nathan Wrigley. Today’s episode features Jonathan Desrosiers—principal software engineer at Bluehost, sponsored through Five for the Future, Core committer, and long-time WordPress contributor. We discuss synchronizing WordPress releases with flagship community events, rebuilding contributor momentum after COVID, mentorship and education initiatives, and how AI and open source intersect to empower builders.

Jonathan: I’ve been contributing to WordPress for over a decade and using it for nearly 20 years. At Bluehost I’m sponsored to work on WordPress; I focus on contributor experience, automation, clarifying processes, and mentorship so more people can participate effectively.

Release moments and community events
In December 2025 a major WordPress release coincided with State of the Word in San Francisco. The team staged a live release moment—people gathered and pressed a big red button—creating a sense of theatre and celebration. That experiment sparked the idea: why not align future major releases with flagship events like WordCamp Asia, WordCamp Europe, and WordCamp US to create synchronized community moments?

Logistics and constraints
Timing releases around events sounds appealing but is difficult in practice. WordCamp organizers set dates based on budgets, venue availability, regional holidays, and travel concerns, not the Core release cadence. Religious holidays, vacations, and year-end breaks also impact developer availability. For example, decembers are often low-productivity months because people take time off.

Another factor is global coverage: release squads must include contributors across time zones so work and monitoring can continue when some team members are offline or traveling. Being at an event should not be a requirement to participate; offline contributors are critical to handle issues if connectivity or other constraints affect those on-site.

Creating memorable, useful release experiences
The goal isn’t just theatrics. Jonathan wants releases to be community celebrations that make people feel part of something larger. There’s value in both paced, meaningful releases and faster feedback cycles. Ideally, users and contributors would both be more aware of upcoming features—like a “coming soon” experience in the dashboard—so people can opt in to test and contribute earlier, rather than only seeing change after auto-updates occur.

Feature branch model and release cadence
One approach is feature-specific branches and releases that let people opt into testing individual features earlier. This model could help advertise specific capabilities and prevent unfinished pieces from slipping into a major release unintentionally. Architectural constraints exist though: many editor components are tightly coupled as packages, so isolating single features for separate release is non-trivial.

Auto-updates and adoption trends
Auto updates have made upgrades seamless for many users, which is partly why users don’t always notice releases. Jonathan looked at adoption data: recent major versions are being adopted faster. For instance, WordPress 6.9 reached 50% of sites in ten days—faster than previous releases—suggesting confidence in stability and auto-updates. This accelerating adoption is a signal that release quality is improving and a point to lean into.

Community health and rebuilding
The community is vital—the code and license matter less without people. COVID disrupted local meetups and WordCamp leadership pipelines: many organizers burned out or stepped away, leaving gaps. Rebuilding requires renewed enthusiasm and deliberate pathways to bring in new contributors.

Global differences matter: APAC communities often show growth and strong meetup activity, whereas parts of the U.S. and Europe have struggled to regain pre-COVID momentum. Societal shifts in how people learn and socialize compound this.

Education, mentorship, and WP initiatives
To attract new contributors, WordPress initiatives are emphasizing education and mentorship: the WP Credits program, contributor mentorship cycles, Campus Connect, and other learning efforts. Successful contributor journeys often start in mentorship programs—mentees become mentors and eventually team leads. But awareness alone isn’t enough; WordPress must be ready to activate newcomers with clear tasks, support, and pathways to continued contribution beyond a single Contributor Day.

Using release events to onboard contributors
Synchronized release events offer opportunities to pilot approaches to onboarding and sustaining contributions. For example, making release testing accessible—providing a zip of the upcoming release, encouraging attendees to install and report compatibility data—can be a low-friction entry point. The challenge is capturing and making meaningful use of that testing data and converting casual testers into repeat contributors.

Appealing to younger generations and changing motivations
Younger people have different habits and expectations. They grew up with powerful, always-connected devices and large closed platforms. Convincing them of open source’s value takes more than rhetoric: it requires showing tangible benefits, career pathways, and experiences that feel relevant and rewarding.

We must also be willing to rethink events and formats. If meetups and WordCamps don’t match what new contributors find exciting—formats, topics, or benefits—attendance will lag. Combining community moments with practical learning (e.g., workshops, contribution sprints) and modern tooling may better attract younger contributors.

AI, empowerment, and open source
AI is changing the landscape. It empowers more people to build and iterate quickly by summarizing and distilling complex information. That lowers barriers to trying things and experimenting with WordPress—people can prototype sites or tools faster. While AI can generate rough solutions, scaling, security, accessibility, and robustness still require human expertise. That ongoing demand for skilled contributors is a positive: tools will change the nature of work but won’t eliminate the need for builders.

There’s also broader appetite for alternatives to walled gardens: renewed interest in RSS, blogging, and decentralised platforms shows people want more control. When closed platforms change policies or limit access, it reinforces open web values and the importance of projects like WordPress.

Looking ahead
2026’s plans—attempting synchronized releases with flagship events, pushing education programs, and experimenting with ways to onboard contributors—are part of a broader effort to reinvigorate community participation and make release moments meaningful. The experiment will teach lessons about logistics, engagement, and how best to scale welcoming pathways for new contributors.

Where to find Jonathan
jonathandesrosiers.com, and he’s desrosej across many platforms. He’s also active in the wordpress.org Slack.

Thanks to Jonathan for sharing insights on release strategies, community rebuilding, mentoring, and the interplay of AI and open source. If you’d like the links and more, check the show notes at wptavern.com/podcast.