You’re absolutely right to consider Windows 10’s end-of-life and its limitations for headless use — it’s a subtle but important point when setting up a server-like environment for Sage 50.
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Where Windows 10 Pro Looks Tempting
• Cheaper licence and widespread availability
• Stable and familiar for users (especially Sage 50)
• Works well in a single-purpose VM on Proxmox
• RDP support is built-in
• Bypasses TPM/UEFI checks easily in a VM⸻
But Here’s the Catch
- End of Support Approaching
• Windows 10 Pro reaches End of Support on 14 October 2025
• After this, no security updates, unless you:
• Buy Extended Security Updates (ESU) (likely expensive)
• Take risks by isolating the VM from external access
• That’s barely 16 months away, so long-term use is questionable
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- Not Truly Headless
• Windows 10 Pro is desktop-first, not server-grade
• GUI must run all the time
• Services (e.g. Sage or RDP) can be interrupted by:
• Login screens
• Update prompts
• User session disconnects
• No native watchdogs, service restarts, or true multi-user logins like Windows Server
• For 5 concurrent users, you can’t legally use RDP on Windows 10 Pro — it only allows 1 interactive session at a time
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So What Are Your Realistic Options?
Option 1: Windows Server 2019 Essentials
• Still sold today, supported until January 2029
• Allows multiple RDP sessions
• Designed for headless use (runs stably with no logged-in user)
• Lower cost than Server Standard
• Lightweight GUI and no domain requirements
• Great fit for small businesses with one server roleOption 2: Windows Server 2022 Standard
• Latest and longest supported (until 2031)
• Best scalability, policies, and remote desktop features
• More expensive and heavier
• Overkill if you’re just running Sage⸻
Recommendation
| Use Case | Best Choice |
|---|---|
| 1–2 users, short-term use | Windows 10 Pro (with upgrade path in mind) |
| 3–5 users, remote/headless use | Windows Server 2019 Essentials |
| 5+ users or domain integration | Windows Server 2022 Standard |
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Conclusion
Windows 10 Pro looks tempting due to price and simplicity, but:
• It’s not future-proof
• It’s not ideal for remote multi-user or headless operation
• It will require replacement or upgrade in under 18 monthsYou’d be better off going with Windows Server 2019 Essentials now and avoiding the migration later — especially since Sage 50 will happily run on it.