Mark, did you ever solve this? If so, how? I'm having the same problem but 
with a USB WiFi dongle. It worked fine with the old method of editing 
/etc/network/interfaces and installing the wifi-reset service. But I've 
upgraded to Debian 8.6 for the beaglebone and the old method doesn't work 
any more. As you say it connects just fine with connmanctl, but doesn't 
reconnect after a reboot, even with "config wifi_*_* autoconnect on". Nor 
does the old wifi-reset service solve the problem.
https://learn.adafruit.com/setting-up-wifi-with-beaglebone-black/configuration#wifi-reset-service

On Friday, 8 January 2016 09:30:13 UTC+10, Mark Grosen wrote:
>
> With the right device tree loaded, the cape works after configuring 
> connman. The problem is that WiFi does not connect after a reboot. I have 
> to manually run "connmanctl connect wifi_blah". After that, things work 
> normally. I can use ifconfig up/down to change state without using 
> connmanctl. It's only after a (re)boot that it does not autoconnect. I have 
> autoconnect turned on for the AP
>
>

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