xthunderheartx - not sure I can answer. Some hints:
the auto-connect is temporarily ignored in connman if there is some lower level disconnect or connection failure error. This way connman will not try to re-connect to AP that is constantly failing.
User is able to manually re-connect the AP and if the connection succeeds, then auto-connect is enabled again.
Are you kiddin'? That absolutely answers the question! That has to be what is happening. Of course it brings up another question which is can connman's behavior be changed to always try to autoconnect. In our application the Galileo has now wired Ethernet (the RJ45 is literally removed), no console (we use ttys1 to talk to a PIC, ttyS0 to talk to a modem) and lives in an unattended environment. Manual intervention is not really an option.
While I have you can you tell me if there is a new image for IOTDK image in the works? I notice there is a 2.0 repo on the site but the released image is 1.5 right? I have been hoping for some package upgrades, though it looks like most at still at the 1.5 versions. Connman is one I was hoping for as I couldn't get Wifi Direct (p2p) working and have to resort to plain old tethering. Plus you tell people on other channels like irc:#connman you are running 1.25 and their immediate response is "upgrade".
Thanks for your help Matthias!