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You can select where to transfer files by clicking the "Devices" option in the Guacamole menu. That will give you a file manager type menu where you can select the directory to transfer files into. Please note that you will only be able to read or write files in directories that your user account would have access to. This means unless you've created directories where you can write, by default you'll only be able to write into your home directory, /tmp, and mounted volumes (/vol_X), etc

Double-clicking on any directory will change the current location of the file browser to that directory, updating the list of files shown as well as the "breadcrumbs" at the top of the file browser. Clicking on any of the directory names listed in the breadcrumbs will bring you back to that directory, and clicking on the drive icon on the far left will bring you all the way back to the root level.