As stated above, when rebooting the insync-headless get_status command reports “ERROR”, while get_errors reports “None”. My suspicion is that since I have the data to be synced in a samba mounted share in fstab the crontab line starts the service before the filesystem is ready, it then proceeds to barf and give up.
Is there a way to delay starting insync at boot by a couple of minutes? Else it should keep trying every 15 seconds or so to see if the filesystem is available.