There are two ways to add custom files to your Canary's Windows File Share service:
Right-clicking on folders in the tree and selecting "New > Upload a Custom File"
Opening your bird to SMB connections and uploading your files directly
Unfortunately, both options have downsides due to the way your Console communicates with Canaries.
When using option one, you are limited to a maximum file size of 50 kB, as the Console cannot send larger files directly to the Canary. This limit can be overcome by uploading directly via SMB, but because of the file size restriction, these files cannot be retrieved by the Console later. This prevents these files from being shipped with a custom personality, as the Console has no knowledge of their contents.
If you intend to duplicate your File Share setup with a custom personality, you can freely make use of option one for adding files (and dragging files around in the tree to re-organize them) – all of these changes will be reflected on your other birds. The second option will still reflect in the original bird, but the custom personality just won’t take the files with it.
Sorry for any trouble or inconvenience this has caused, we’re working to make it better.