Hi Brett,

You are right, multiple uploads should work as you describe. If you don't have any firewall issues from the location you are uploading files, and if you haven't already, please contact Support so we can look into this further. Sign In to my.pogoplug.com and 'Submit a support ticket' using 'Help Center'.

In the meantime, you can try to install Pogoplug Remote Access Software from http://pogoplug.com/expansion Software displays Pogoplug as a mapped drive in Windows so you can copy and paste or drag and drop files to your Pogoplug attached drive. Both the Free Trial and the Premium version include this feature. The Premium license is required only if you want to stream content FROM your computer.

Kindest Regards,
Christopher Louie
on behalf of the Pogoplug Team