wanderlustig
Just remembered: that time, a warning popped up about the navigation falling back to a slow method. Tried the same route now (using the August 2017 map) and it gives the same route Pakenhamin had: east along the freeway to the Montague Street exit, then U-turn back onto the freeway and continue west. Could be that it weights that ridiculous freeway excursion as more efficient than going through potentially five sets of traffic lights. If you set the Todd Road freeway onramp as the destination, it just does the obvious Cook Street/Todd Road route. So I guess it's a routing heuristic issue.