When I attempt to send an outdoor ride to my Wahoo Bolt, I always have to reconnect. When the ride is synced to my Bolt there is no option to start the workout. The options that display on my Bolt are Back, End and 100%.
Strange, I will test this on Monday.
Thanks!
So wow… I see you were one of the first people to signup for ERGdb / TrainerDay 
So I tested sending this workout to my Elemnt as outdoor workout.
I have no problems connecting. I did it 2 times. It showed start both times like this.
The first time I went to Elmnt iOS app and clicked. “SELECT WORKOUT PLAN” like below
And it immediately popuped up in my Elemnt to start just like above.
The second time, it gives an error since I already sent it to my device. So I have to go to planned workouts in the Elemnt and select it and then I also see start. Once I start I see forward and backward…
When you say you always have to re-connect do you mean in our connection settings? If so I can have my developer investigate that. Maybe try the workout I did above. Maybe it is something with a specific workout.