Techniques for using traceroute with tunnels and cloud-based systems for determining measures of network performance are presented. Systems and methods implemented by a traceroute application implementing a Transmission Control Protocol (TCP) stack in a processing device include sending a plurality of TCP packets via a raw socket to perform a trace to a destination; receiving responses to the plurality of TCP packets; detecting the responses in the TCP stack and diverting the responses to the raw socket; and aggregating the responses by the traceroute application to determine details of a service path from the processing device to the destination.