Whatever the tool says, do this today: if you haven't enrolled in ESU, your Windows 10 PC is receiving no security patches. Enrolling is free for most people and takes five minutes, and it removes the time pressure from every other decision. Here's how.
How the recommendation is made
A few firm rules. Hard blockers override preferences: if you need software that doesn't exist on another platform, the tool tells you to stay on Windows even if you'd prefer otherwise, because that's the true answer. The free option is always mentioned first where it applies. And "I want things to stay familiar" is treated as a legitimate requirement, never routed to the most disruptive option.
| Question | Why it matters |
|---|---|
| Windows 11 eligibility | If your PC is eligible, the free upgrade is usually the simplest path. If it isn't, that's what opens up the other options. |
| Software you rely on | The single biggest factor. Macro-heavy Excel, Adobe, QuickBooks Desktop, Access and industry software are blockers, not inconveniences. |
| Gaming | Competitive multiplayer with kernel-level anti-cheat cannot work on Mac or Linux by any route. Single-player is a different picture. |
| Budget | There is a genuinely free path. We won't recommend spending unless there's a reason. |
| Appetite for change | Changes the answer more than anything else. |
