The Problem: Attempting to attach a file to an email in Gmail/Apps Email via Chrome OS, Gmail only allows the user the option to attach files from the "Downloads" directory. Unless you've save a file in this directory, you cannot send it as an attachment in Gmail on your Chrome OS enabled device.
The Reason: Application developers who have created browser/cloud based applications have done so assuming users would be using their apps on traditional operating systems where the user has full access to the filesystem. For this reason, when prompting the user to save something, it brings up a file browser that dumps users into some "default" file path. In the case of Aviary, it dumps the user into /
The Solution: When prompted with a save file dialog or a browse dialog, navigate to - /home/chronos/user/Downloads/ - and save your files there. From this spot, users will be able to access files via the "Downloads" shortcut (control+o) or from within Gmail when attempting to attach files.
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