This invention relates to methods and devices for compensating for path asymmetry, particularly with reference to time and frequency synchronization. The invention has particular application where time and frequency synchronization over packet networks using, for example, the IEEE 1588 Precision Time Protocol (PTP) is being carried out. Typically communication path delays between a time server (master) and a client (slave) are estimated using the assumption that the forward delay on the path is the same as the reverse delay. As a result, differences between these delays (delay asymmetries) can cause errors in the estimation of the offset of the slave clock from that of the master. Embodiments of the invention provide techniques and devices for compensating for path delay asymmetries that arise when timing protocol messages experience dissimilar queuing delays in the forward and reverse paths.