What 2025 taught sysadmins and what to expect in 2026

By the time December rolled around, most sysadmins were asking the same existential question: Was 2025 actually 10 years long? From the scramble of forced AI adoption to the long-anticipated Windows 10’s end of life, plus growing concerns about phishing and a pair of Cloudflare outages that caught half the internet off guard, 2025 had plenty of moments that made even veteran sysadmins pause and stare at their screens.

In PDQ’s final webinar of the year, Brock Bingham (senior content engineer at PDQ), Andrew Pla (community manager at PDQ), and Dylan Courtade (desktop engineer at 4Front Credit Union) sat down to recap what actually mattered in 2025 — what was hype, what delivered hope, and what sysadmins need to carry with them into 2026. The conversation uncovered a clear theme: 2025 wasn’t a “normal” IT year. It was a pivot point, and 2026 will be shaped by everything we learned the hard way.

Let’s dig in.

AI showed up ... everywhere

AI adoption accelerated in 2025, but most tools delivered hype instead of maturity.

If you felt like 2025 turned into one long AI press release, you weren’t alone. Dylan summed it up with a phrase that should probably be on a T-shirt by now: forced AI adoption.

Instead of asking whether AI was ready, vendors simply strapped it to their products and shipped it.

Shadow IT played its part too. As Brock explained, companies realized that unless they offered sanctioned AI tooling, employees would simply use whatever they found on the internet — company data and all.

Andrew took a more skeptical stance. Yes, AI tools have potential. But as he pointed out, actual ROI is still … elusive. “There's definitely a lot of viability with some of the tools we're seeing,” he said, “The rest are kind of TBD”

The consensus: AI has momentum, not maturity. And sysadmins are the ones stuck cleaning up after both.

Windows 10 end of life hit harder than expected

Windows 10 reached end of life in 2025, forcing widespread audits, upgrades, and cleanup across IT fleets.

And while no sysadmin was surprised, many were definitely annoyed.

It wasn’t just Windows 10, either. Office 2016, Office 2019, and even Windows 11 23H2 also said their goodbyes. That meant a year of version audits, fleet upgrades, confused users — and for many teams, a crash course in Microsoft’s increasingly complex naming schemes.

Andrew said it best: “You have to memorize this whole graph of when things expire. And they got these weird names, like 23H2. It takes something that should be kind of simple, and all of a sudden, you're having to memorize things.”

The takeaway heading into 2026? Version churn isn’t slowing down, so whatever upgrade strategy your team used this year … you’ll probably need it again soon.

The new Outlook rollout was a masterclass in “not like this”

Microsoft pushed the new Outlook client to Windows devices in 2025, but missing features and mailbox issues made most users reject it.

Microsoft continued its theme of “we promise this is fine” by pushing the new Outlook client to Windows machines — whether people wanted it or not.

Dylan’s organization tried a fair approach: Get user feedback. Their verdict was immediate. The new Outlook lacked core features, struggled with shared folders, and generally felt like the web version but … clunkier.

The reality? Most users don’t want “new.” They want “works.” Outlook wasn’t quite there yet in 2025.

Cloudflare outages reminded everyone the cloud is someone else’s computer

Cloudflare outages in 2025 disrupted dependent services across the internet, highlighting how shared infrastructure failures cascade quickly.

When an upstream service hiccups, organizations everywhere suddenly go quiet. Dylan’s team didn’t get hit directly, but their banking tools did. The diagnosis, once again, was the most sysadmin sentence ever spoken: “It’s always DNS.”

Andrew noted that the collective reaction to outages has shifted. Ten years ago, a downtime spike was a national event. In 2025? A shrug and a “guess I’ll check back later.” Whether that’s grace or exhaustion is up for debate.

VMware and Broadcom triggered a mass virtualization migration

If there was a single storyline that united sysadmins worldwide, it was this one. Renewal costs skyrocketed. Organizations that had been all-in on VMware for a decade suddenly began Googling alternatives at 2 a.m. Andrew called it what it was: a wake-up call about vendor lock-in.

2025 taught IT teams that being all-in on a platform is great ... until the platform changes the rules.

PDQ Connect’s biggest 2025 wins

PDQ Connect shipped major platform upgrades in 2025 that improved deployment precision, macOS support, visibility, and multitenant control.

A few highlights included:

• Package and step conditions — a massive boost for precision deployments.

• macOS support, including remote control and shell access.

• A full Software tab for faster visibility across fleets.

• Multitenancy, perfect for MSPs or big orgs with messy org charts.

• 20 GB file support, unlocking Autodesk-sized deployments.

For a cloud-native tool, the leaps were substantial ... and very clearly driven by sysadmin feedback. As Brock said, “We rely heavily on the community to drive our features and our roadmap. So definitely let your voices be heard. Send in your requests.”

What sysadmins should brace for in 2026

Many of 2025’s challenges will intensify in 2026. Sysadmins should expect faster AI evolution, sharper security threats, and a push toward unified tooling.

AI gets more powerful — and more exhausting

When the panel looked ahead to AI in 2026, Dylan didn’t ask for bigger models or flashier features. He just wanted a contextual, platform-agnostic assistant that can see what you’re working on and actually help — basically “Clippy on steroids,” as Dylan calls it, but without the hallucinations or the bad advice that could wreck a system. He also warned that with so many AI experiments happening at once, AI fatigue is inevitable if things don’t get simpler.

Andrew agreed, predicting that the real wins next year will be practical ones: sidecar-style assistance, smarter tab completion, and better search and help desk workflows. Everything else is still up in the air.

Brock was hopeful but wary. He’s frustrated by vendors — particularly Microsoft — baking AI into products and raising prices for features many companies never asked for. “I’m not against AI,” he said. “I’m against the hype.” And until AI consistently delivers what people expect, he’s not convinced the value is there yet.

Unified tooling becomes a survival strategy

Teams are tired of juggling five dashboards. Expect consolidation, integrations, and platforms that handle more out of the box.

Phishing gets terrifyingly real

Deepfake voices. Perfect grammar. Video impersonations. If 2025 was the setup, 2026 is the escalation.

Passkeys finally take off

Windows Hello and passkey support are poised to save help desks from a lifetime of password resets.

PowerShell becomes even more essential

With AI generating scripts — sometimes disastrously — sysadmins who actually understand PowerShell will stand out more than ever.

What’s next for PDQ Connect in 2026

Brock couldn’t share everything, but here’s what he could confirm:

• PowerShell Scanner (the crown jewel of Deploy & Inventory parity)

• Package folders for cleaner organization

• macOS package library support with prebuilt packages for easy automation

• More multitenancy controls, including package sharing

• A major slate of integrations, details still sealed in the vault

Final thought: 2025 wasn’t chaos — it was acceleration

2025 forced sysadmins to adapt quickly to rapid platform changes, AI disruption, and vendor-driven turbulence.

But it also made teams smarter, more cautious, more strategic, and more aware of risk.

As we look ahead to 2026, one thing is clear: Sysadmins won’t just adapt. They’ll build systems that are better, tighter, and far more resilient than the industry’s moving parts.

And yes — with fewer Outlook surprises ... we hope.