One example method is provided for detecting end-to-end packet loss and retransmission occurring in a connection of a network environment. The method can include monitoring packets transmitted from a sender to a receiver and acknowledgement packets from the receiver to the sender using a probe located in a path between the sender and the receiver in the network environment; identifying, by the probe, a first packet as a possibly-retransmitted packet if the first packet has a fall back sequence number; classifying, by the probe, the first packet as a retransmitted packet using one or more conditions based, at least in part, on one or more of the following: characteristic(s) of the possibly-retransmitted packet, characteristic(s) of sequence numbers observed by the probe, and characteristic(s) of acknowledgements observed by the probe.