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Connecting via bluetooth or trying to connect via wired connection?
I have a 20s (similar function). If the bike shuts down (say at the gas pump). The Sena will automatically reconnect when you fire the bike back up. I personally do not pair the gps to helmet, I found that when traveling, every time the GPS speaks, the audio connection is dropped and has to reconnect after each GPS prompt. But the GPS will automatically run the prompts thru the bikes audio system and simply mute the audio for a second during the prompt. And there's no delay waiting for a connection to re-establish. Not playing audio, tune the audio system to (auxiliary) all will be quiet until the GPS speaks. True you will not get caller ID on the GPS screen, But I personally prefer not to.
Added Note: When pairing, it really helps to be away from all other Bluetooth sources.
I simply turn on my Sena, put on my helmet, hear it confirm connection to my iPhone, and as the bike fires up I hear it confirm connection to the audio system ( or when I turn on audio).