When trying to attach a file located in /Users/"user"/ dir to a gmail email, the /Users/ folder doesn't exist, and there is no top level directory (i.e. /) for me to navigate to. The workaround is that I am forced to copy the file to one of my "favorites" folders so that I can actually choose the file. Verified this issue does not occur within the Finder app, however also verified that Windows does not have this problem.

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    Please help me understand this. How are you trying to get to /? Which application are you using. – At0mic Jun 9 '16 at 15:20
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    Can you post a screenshot? – Billy Jun 9 '16 at 16:32

Found the solution. At the top of the little "pop down" window that shows your files to attach, I had to click on the drop down box (where it currently shows "Documents") to choose a different directory:

enter image description here

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