"We won," the messenger announced, and then collapsed, and so becoming the most renowned victim of connectivity, spearheading the Marathon legacy. Pheidippides' death encapsulates the quest for and risks of connectivity; we see it as tragic and unnecessary because we now take it for granted that a message and its messenger can be separated. But when the message is the messenger, as in, reporting for work, the risk is real, witnessed by over a million annual road deaths globally as well as the ongoing coronavirus pandemic. In this piece, we look at the concept of connectivity's many facets, the range of its manifestations, and its outcomes to understand what role planners can play in shaping its effects.