Comparison: Windows 11 Per-Seat + File Server vs. Windows Server 2025 with RDS

System Comparison Table

Aspect	Windows 11 + Per-Seat Licences + File Server	Windows Server 2025 + RDS + Centralised App
Licensing	✅ Simple and legal with per-seat licences	✅ Legal if RDS CALs are purchased for each user
Installation	Installed locally on each user’s PC	Installed once on server, accessed by all users
User Experience	Software runs natively, fast	Users work via RDP — minor lag possible
Simultaneous use	Depends on app’s support for shared data	Full, concurrent use — each user has isolated session
Remote access (e.g. Tailscale)	Only file server is shared; app must be local	Entire system accessible remotely with one login
IT Complexity	Lower — simpler setup, less to maintain	Higher — server must be maintained, secured, backed up
Security	Medium — relies on each PC’s patch level	Higher — single point to secure and audit
Hardware cost	Multiple powerful PCs needed	One powerful server can reduce endpoint hardware needs
Backup management	Shared files must be backed up; users responsible for app	Server backups protect all data and app state together
Multi-user file access	Risk of conflict if app isn’t designed for concurrent access	No risk — app runs separately per user session
Software updates	Each PC must be updated separately	Update once, everyone benefits
Support burden	Distributed — users may break things individually	Centralised — easier to support a single environment
Audit trail & access logs	Hard to track across devices	Central logging of sessions, activities, login times
Scaling	Easy to add users, but app install needed each time	Easy to scale if server is powerful enough
Single point of failure	Less risk — failure of one PC affects only one user	More risk — server failure affects all users

Risk Assessment Summary

Risk Type	Windows 11 + File Server	Windows Server 2025 RDS
Licensing risk	✅ Low	✅ Low if licensed properly
Data loss risk	⚠️ Medium (local PCs may not be backed up)	✅ Low (centralised backups possible)
User error risk	⚠️ Higher (5 separate environments to maintain)	✅ Lower (admin controls full system)
Security risk	⚠️ Medium (5 devices to secure)	✅ Lower (single hardened environment)
Update drift	⚠️ Likely (PCs updated at different times)	✅ Consistent
Remote access reliability	⚠️ App must support remote file access	✅ Full RDP access anywhere
Scaling/expansion risk	✅ Easy (if app supports it)	⚠️ Depends on server capacity

Summary Recommendations

Situation	Best Choice
You need 5 independent users, each on their own PC, and the app works well over a file server	Stick with Windows 11 + per-seat licences
You want to centralise control, simplify support, improve audit/security, or support larger teams	Move to Windows Server 2025 + RDS
You want seamless remote access for everyone	Windows Server 2025 + Tailscale
Your app struggles with file conflicts or shared file access	Windows Server 2025 (single install)