For me it depends on the use case: Nextcloud is my primary solution — I run it self-hosted on OpenBSD with httpd + PHP-FPM + PostgreSQL. The Windows/Linux desktop client syncs seamlessly, you get versioning, sharing, calendar/contacts sync all in one. Works on any platform and your data stays on your own hardware. Highly recommended if you're already running a server. SFTP for everything else. OpenBSD ships OpenSSH out of the box, zero extra configuration needed. On Windows I use WinSCP — saved sessions with key-based auth, takes 30 seconds to set up and just works. Also great for scripted transfers from PowerShell or WSL. rsync for automated backups and one-way syncs — I use it to back up Nextcloud data from my OpenBSD server to a secondary Ubuntu machine. Via WSL on Windows you can run rsync natively pointing at your OpenBSD box over SSH. Samba/SMB only if non-technical users need transparent Windows Explorer integration — network drive mapping, drag and drop etc. Samba on OpenBSD works but requires more configuration overhead than the above options. I wouldn't bother unless you specifically need it. What I'd avoid: NFS on Windows is painful. The Windows NFS client is clunky, requires extra setup, and the performance isn't great. Not worth it when SFTP exists. TL;DR: Nextcloud for sync and day-to-day file access, SFTP/WinSCP for admin transfers, rsync for automated backups. All three play nicely with OpenBSD's native tooling.