Downloads for most users does require Plex Pass for the person downloading. However we did grandfather those where the server owners and downloader user accounts were created before a date when we changed that. A grid explaining that can be found here https://support.plex.tv/articles/downloads-sync-faq/
If you friend is using the new version of the app released a couple days ago then there is an issue with it not respecting the grandfathering which we are currently fixing.
