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Automatically Reconnect to Wireless Network

In order to automatically reconnect the Raspberry Pi to the wireless network, edit /etc/network/interfaces.d/wlan0 and configure the wireless network for the wlan0 interface. The following example is meant to connect to a hidden WPA-PSK network:

auto wlan0
allow-hotplug wlan0
iface wlan0 inet dhcp
    wpa-scan-ssid 1
    wpa-ap-scan 1
    wpa-key-mgmt WPA-PSK
    wpa-proto RSN WPA
    wpa-pairwise CCMP TKIP
    wpa-group CCMP TKIP
    wpa-ssid "My Network"
    wpa-psk "mypassword"

where:

My Network is the SSID/network name of the hidden network and,
mypassword is the secret network key.

Finally, copy /etc/wpa_supplicant/ifupdown.sh to /etc/ifplugd/action.d/ifupdown and restart the machine.

Update Firmware

Some raspberry Pis have issues such as failing to reboot the system when issuing a reboot command. Most of these issues can be fixed just by upgrading the firmware. Raspbian has a tool named rpi-update that can be ran as root in order to update the firmware.