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Adding media to external USB drive

So right now I have a 1TB USB drive directly connected to my RPi through a powered USB 3.0 docking station. My RPi is connected to my Airport router via ethernet. What I'm doing currently to add media is disconnecting the drive from the RPi and connecting directly to my desktop to add media. I would like to be able to keep the drive connected to the RPi and add media through the network but I have no idea how to do this. How are most of you doing this?

Thanks in advance!
I could add a samba share, but the problem [at present] is that I have no control over the mountpoint names. I suppose I could share /media which should work for most users......

I'm open to ideas, and can implement them for you in the next release of PlexPi.

Robbie Ferguson // The Bald Nerd

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I'm also looking for the same info. Any ideas.
I have VNC enabled on my raspberry pi 3b+ and will send files from my laptop to the pi via vnc. It is called file transfer or fetch in vnc. Hope this helps.
I use Filezilla from my imac and I upload my media into the hdd connected to my pi 3b+
I had some trouble to give the right permissions, but now it work for me.
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