We present new measurements of the large-scale bulk flows of galaxy clusters based on five-year WMAP data and a significantly expanded X-ray cluster catalog. Our method probes the flow via measurements of the kinematic Sunyaev-Zel'dovich (SZ) effect produced by the hot gas in moving clusters. It computes the dipole in the cosmic microwave background data at cluster pixels, which preserves the SZ component while integrating down other contributions. Our improved catalog of over 1000 clusters enables us to further investigate possible systematic effects and, thanks to a higher median cluster redshift, allows us to measure the bulk flow to larger scales. We present a corrected error treatment and demonstrate that the more X-ray luminous clusters, while fewer in number, have much larger optical depth, resulting in a higher dipole and thus a more accurate flow measurement. This results in the observed correlation of the dipole derived at the aperture of zero monopole with the monopole measured over the cluster central regions. This correlation is expected if the dipole is produced by the SZ effect and cannot be caused by unidentified systematics (or primary cosmic microwave background anisotropies). We measure that the flow is consistent with approximately constant velocity out to at least 800 Mpc. The significance of the measured signal peaks around 500 h ^–1 ₇₀ Mpc, most likely because the contribution from more distant clusters becomes progressively more diluted by the WMAP beam. However, at present, we cannot rule out that these more distant clusters simply contribute less to the overall motion.