A request from a client device is received at a first one of a plurality of compute nodes at a first one of a plurality of data centers of a distributed cloud computing network. A destination of the request is determined. An optimized route for transmitting the request toward an origin server that corresponds with the destination of the request is determined, where the optimized route is based on at least in part on probe data between data centers of the distributed cloud computing network for a plurality of transit connections, and where the optimized route has an IP address that encodes an identification of which of the plurality of transit connections is to be used to deliver the request. The request is transmitted to a next hop as defined by the optimized route over the identified one of the plurality of transit connections.