We assess to what extent seven state-of-the-art dynamical prediction systems can retrospectively predict winter sea surface temperature (SST) in the subpolar North Atlantic and the Nordic Seas in the period 1970-2005. We focus on the region where warm water flows poleward, i.e., the Atlantic water pathway to the Arctic, and on interannual-to-decadal time scales. Observational studies demonstrate predictability several years in advance in this region, but we find that SST skill is low with significant skill only at lead time 1-2 years. To better understand why the prediction systems have predictive skill or lack thereof, we assess the skill of the systems to reproduce a spatio-temporal SST pattern based on observations. The physical mechanism underlying this pattern is a propagation of oceanic anomalies from low to high latitudes along the major currents; the North Atlantic Current and the Norwegian Atlantic Current. We find that the prediction systems have difficulties in reproducing this pattern. To identify whether the misrepresentation is due to incorrect model physics, we assess the respective uninitialized historical simulations. These simulations also tend to misrepresent the spatio-temporal SST pattern, indicating that the physical mechanism is not properly simulated. However, the representation of the pattern is slightly degraded in the predictions compared to historical runs, which could be a result of initialization shocks and forecast drift effects. Ways to enhance predictions, could be through improved initialization, and better simulation of poleward circulation of anomalies. This might require model resolutions in which flow over complex bathymetry and physics of mesoscale ocean eddies and their interactions with the atmosphere are resolved.