We improved this in Transfer 2.2.3.102 (Setup v2.2.3)
Now, if a project isn't uploaded, color of "Reload" button will be turned red and you will see this description:

[18.05.2015 14:12:43:905] Panel(1): Updating has started
[18.05.2015 14:12:47:000] Panel(1): Disconnect
[18.05.2015 14:12:47:005] Panel(1): Updating has failed

Sincerely yours,
Oksana Storozheva
iRidium mobile Team