The Unthinkable Migration: 1500+ Windows Devices to Mac
Let's be honest—when you first heard about an organization switching every single Windows device to Mac, you probably thought one of two things: "That's insane" or "That's brilliant." There's rarely any middle ground in the Windows vs. Mac enterprise debate. But here we are in 2026, looking back at a year-long experiment that actually happened. Not just a few test devices, but a full-scale migration of 1500+ endpoints.
The original Reddit post from a sysadmin detailing this migration sparked one of the most heated discussions in r/sysadmin history. Over 1,100 upvotes and 173 comments showed just how polarizing this topic is. People weren't just curious—they were invested. They wanted to know: Did it work? Was it a disaster? Did users revolt? And most importantly for IT teams considering similar moves: What's the actual day-to-day reality of managing a Mac-first enterprise?
I've spent the last week diving deep into that discussion, talking with IT professionals who've made similar transitions (though rarely at this scale), and analyzing what this means for automation and DevOps teams in 2026. What follows isn't just a summary—it's the expanded, expert analysis that addresses every question raised in that thread, plus the practical realities you won't find in vendor whitepapers.
The Hardware Reality: M-Series Macs After 12 Months
Here's the first thing everyone wanted to know: Did the hardware hold up? The organization standardized on M3 Air and Pro models initially, with some M4 replacements trickling in. And the results here are actually pretty straightforward.
From a pure hardware reliability standpoint, the numbers are impressive. "Everyone is still using the same laptop they got," as the original poster noted. That's not nothing when you're talking about 1500+ devices. Compare that to the typical Windows laptop refresh cycle where you're dealing with hardware failures, battery issues, and performance degradation that starts showing up around the 9-month mark.
But here's what the original discussion didn't fully explore—the hidden hardware costs. Yes, the M-series Macs are reliable. But when something does go wrong (and something always goes wrong), you're dealing with Apple's repair ecosystem. No more swapping out RAM modules or popping in a new SSD. It's whole-unit replacements or Apple-certified repairs. For a 1500-device fleet, that means you need a different kind of spare inventory strategy.
One commenter in the thread put it perfectly: "The uptime is great until you need a same-day repair for an executive whose MacBook won't boot. Then you realize there's no 'loaner SSD' option." This is where your automation strategy needs to account for hardware management differently. You can't just image a new drive and swap it in—you need automated backup and restore processes that work seamlessly when a user gets a replacement unit.
Management Stack: Apple Business Manager + Jamf = Success?
The original poster mentioned they're "still using Apple Business Manager and Jamf," which prompted about a third of the discussion questions. People wanted to know: How does this actually work at scale? Is it really comparable to Microsoft's ecosystem?
Let me break this down from experience. Apple Business Manager (ABM) is your source of truth for device ownership and deployment. It's where devices get automatically enrolled in your MDM (Jamf, in this case) right out of the box. No user intervention needed. This is huge for automation—imagine shipping a laptop directly from Apple to a new hire, and it configures itself before they even open the box.
But here's the catch that several commenters pointed out: ABM requires buy-in from your procurement team. Every Mac has to be purchased through authorized channels to appear in ABM. If someone buys a Mac from Best Buy for "urgent needs," you're back to manual enrollment. This isn't a technical limitation—it's a process one. And at 1500+ devices, process breaks down more often than technology.
Jamf, meanwhile, has matured significantly. The automation capabilities are robust if you know how to use them. But as one experienced Mac admin in the thread noted: "Jamf can do almost anything, but the learning curve is steeper than people admit. It's not Intune where you can figure out basics in an afternoon."
For DevOps teams, this is critical. Your infrastructure-as-code mindset translates well to Jamf, but you're working with a different paradigm. Instead of Group Policy Objects, you're dealing with configuration profiles. Instead of Windows Update rings, you have software update management. The concepts map, but the implementation details matter.
The Software Compatibility Question Everyone Asked
This was the biggest concern in the discussion thread: "What about our legacy Windows applications?" "Does finance's weird Java-based tool work?" "What about CAD software?"
The reality, as it often is, is nuanced. For most standard office workloads—Microsoft 365, web apps, communication tools—the transition was seamless. In fact, many web-based tools actually perform better on Apple Silicon because of Safari's efficiency and the M-series chips' performance.
But for specialized Windows applications? That's where things get interesting. The organization apparently used a combination of approaches:
- Virtualization (Parallels or VMware Fusion) for must-have Windows apps
- Web app conversions where possible
- Actually convincing some departments to switch to Mac-native alternatives
Here's what most people don't consider: The cost of maintaining Windows compatibility isn't zero. If you're running Parallels with Windows licenses on 1500 Macs, you're paying for that. If you're maintaining a separate Windows server for Remote Desktop Services, that's infrastructure and licensing costs. The question becomes: At what point does maintaining Windows compatibility cost more than finding alternatives?
One commenter shared a brilliant insight: "We found that 80% of our 'Windows-only' apps were actually just apps no one had questioned in years. When we told departments they'd need to budget for Windows VM licensing, suddenly 60% of those apps had Mac alternatives."
User Experience & Support Tickets: The Real Metric
Everyone in the discussion wanted to know: Did users actually like it? Were support tickets through the roof? This is where the story gets most interesting.
According to the original poster, user satisfaction was high. But let's read between the lines here. When you give someone a new M3 MacBook Pro to replace a 3-year-old Windows laptop, of course they're happy initially. The real test comes months later when the novelty wears off.
Several commenters who'd done smaller-scale migrations shared their experiences. The pattern was consistent: Initial excitement, followed by a learning curve period (2-3 months), then settling into a new normal. The key differentiator? Training. Not just "here's how to use a Mac" training, but specific workflow training.
"We made the mistake of assuming Excel is Excel," one admin wrote. "But keyboard shortcuts, right-click menus, even how you save files—it's all just different enough to frustrate power users."
Support ticket patterns changed too. Fewer hardware-related tickets (no more "my fan sounds like a jet engine"), but more software and workflow questions. The automation opportunity here is in knowledge base integration and self-service. With Jamf's Self Service app, you can push how-to guides and troubleshooting steps directly to users.
But here's the pro tip no one mentioned in the thread: Monitor your most common support issues, then automate fixes for them. If users keep having Wi-Fi issues after sleep, create an automated remediation script. If certain printers always need re-adding, automate the printer deployment. This is where DevOps thinking transforms Mac management from reactive to proactive.
Security & Compliance: Surprisingly Straightforward
This was the quiet surprise in the discussion. Multiple security-focused admins chimed in to say that Mac management had actually improved their security posture in some ways.
Here's why: Apple's hardware and software integration creates a more consistent security baseline. Every M-series Mac has the same security features enabled by default—Secure Boot, Touch ID, hardware encryption. You're not dealing with different OEM implementations or users disabling security features.
With Jamf and ABM, you can enforce compliance policies automatically. Need to ensure FileVault is enabled? That's a configuration profile. Want to restrict certain system settings? That's a restrictions profile. The automation here is declarative—you define the desired state, and the MDM enforces it.
But (and there's always a but) the patch management story is different. Apple releases macOS updates on their schedule, not yours. While you can defer updates, you can't create custom update packages like with WSUS. This requires a different automation approach: testing updates more frequently, communicating changes to users, and having rollback plans.
One security admin in the thread made an excellent point: "The biggest security win wasn't technical—it was psychological. Users take Mac security more seriously. They don't try to disable things as much because they assume Apple knows what they're doing." Whether that's true or not, perception matters in security.
Cost Analysis: The Elephant in the Server Room
Let's talk money, because everyone in the discussion did. The initial reaction is always: "Macs are more expensive upfront!" And they're not wrong. An M3 MacBook Pro costs more than most business Windows laptops.
But—and this is critical—the total cost calculation changes at scale. Here's what often gets missed:
- Longer usable lifespan: If 1500 Macs last 4 years instead of 3, that's 25% fewer refresh cycles
- Lower support overhead: Fewer hardware issues means fewer IT hours spent on repairs
- Reduced software licensing: No Windows Pro licenses, potentially fewer third-party utilities
- Energy efficiency: M-series Macs use significantly less power, which matters at scale
One commenter did the math for their 200-device organization: "When we factored in 3-year TCO including support time, software, and expected resale value, Macs were 15% more expensive. But when we extended to 4 years (which Apple supports), they were actually 8% cheaper."
The automation angle here is inventory and lifecycle management. With ABM and Jamf, you have complete visibility into every device's status, warranty, and even battery health. You can automate replacement workflows based on criteria like "battery health below 80%" or "warranty expiring in 90 days." This proactive approach prevents emergency replacements and spreads costs more predictably.
Automation Opportunities Most Teams Miss
Based on the discussion and my own experience, here are the automation opportunities that most organizations overlook when managing Mac fleets:
1. Zero-touch deployment automation: With ABM and Jamf, you can automate the entire setup process. New device arrives, user turns it on, and everything configures automatically—Wi-Fi, VPN, apps, printers, everything. But most teams only automate 80% of it. That last 20% (department-specific software, user preferences) still gets done manually. The trick is using Jamf's smart groups and scope-based automation to handle those edge cases.
2. Self-service app catalogs: Jamf Self Service is incredibly powerful, but most organizations underutilize it. Instead of just offering optional apps, create intelligent workflows. For example: User requests "Design Suite," system checks if they're in the marketing department, approves automatically, installs, and notifies them. This reduces IT ticket volume dramatically.
3. Automated compliance reporting: With web scraping and data extraction tools, you can automate the collection of compliance data from various sources. Need to verify that all devices have the latest security patches? Automate the report generation. This is especially useful for organizations with regulatory requirements.
4. Integration with other systems: Jamf has a robust API. You can integrate it with your HR system to automatically deprovision devices when someone leaves. Connect it to your network monitoring to correlate device health with network issues. The automation potential here is limited only by your integration creativity.
Common Pitfalls & How to Avoid Them
Reading through the 173 comments, several patterns of failure emerged. Here's what goes wrong and how to prevent it:
Underestimating the learning curve: Not for users—for IT staff. Your Windows admins need time to learn Mac management. As one commenter put it: "We tried to manage Macs like Windows devices for six months before admitting we needed to think differently." The solution? Invest in training early. Consider bringing in a Jamf consultant for the initial setup.
Ignoring peripheral compatibility: That fancy Windows-compatible scanner in accounting? It might not have Mac drivers. Test every peripheral before migration. And when you need reliable accessories that work seamlessly with Mac fleets, consider Anker USB-C Docks for consistent docking station performance.
Forgetting about management overhead: ABM and Jamf require maintenance. Certificates expire, profiles need updating, new macOS versions break things. Automate your automation management. Set up monitoring for your MDM infrastructure itself.
Assuming "it just works": Apple's reputation for simplicity works against IT teams sometimes. Management expects everything to be effortless. Set realistic expectations early. Document where processes will be different. Communicate that some things will be better, some worse, and some just different.
The 2026 Reality: Is Mac-First Viable?
So, one year later, what's the verdict? Based on this case study and the broader discussion, here's my take:
A Mac-first enterprise is absolutely viable in 2026—if you approach it strategically. The technology has matured significantly. Apple Silicon changed the performance and efficiency equation. Management tools have caught up to enterprise needs.
But—and this is crucial—it's not a simple swap. You're not just changing hardware; you're changing your entire device management philosophy. The automation opportunities are different. The support patterns are different. The cost structure is different.
The most successful migrations (like the one discussed) treat it as a transformation, not just a replacement. They invest in training—for both users and IT staff. They rethink processes, not just platforms. They leverage the unique automation capabilities of the Apple ecosystem rather than trying to recreate their Windows workflows.
For DevOps and automation teams, this represents both a challenge and an opportunity. The challenge is learning new tools and paradigms. The opportunity is building more declarative, user-centric automation systems that actually make life better for everyone.
As we look toward 2027, the question isn't "Can you manage Macs at scale?" We know you can. The real question is: "Should you?" And that answer depends entirely on your organization's specific needs, workflows, and willingness to transform, not just transition.
What's clear from this 1500-device experiment is that the old arguments don't hold up anymore. It's not about which platform is "better" in some abstract sense. It's about which platform better serves your organization's goals—and whether you're prepared to manage it effectively. The tools exist. The proof of concept is done. Now it's about execution.
