Abstract Hurricane Ian made landfall along Florida’s west coast at 1905 UTC 28 September 2022 near the Fort Myers area as a high-impact storm. Here, we examine the potential link between track forecast errors near the time of landfall and errors in both the synoptic-scale upper-level flow and a shortwave moving within that flow. Five days before the actual landfall (0000 UTC 23 September), most model guidance indicated landfall would occur close to where Ian eventually came ashore. But by 0000 UTC 25 September, model forecasts were all forecasting landfall in the Florida Panhandle. One day later, the models again agreed with each other but for a landfall 100–200 km north of Tampa, Florida. By 0000 UTC 27 September, forecast models indicated landfall would occur near Tampa. Model forecasts continued shifting to the right and finally converged on Punta Gorda, Florida, as the landfall location, less than 24 h before landfall. In this short article, we hypothesize that the track of Ian depended on subtle interactions with an extratropical wave in the middle and upper atmosphere. Deterministic and ensemble model forecasts reveal that the interactions were very sensitive to the characteristics of this wave and the synoptic-scale flow in which the wave was embedded. A 1–2-dam difference in the geopotential heights played a major role in whether Ian moved north into the Panhandle or toward the east, making landfall in central Florida. Significance Statement The purpose of this work is to look at possible causes of error in forecasts of Hurricane Ian’s landfall with the intent of saving lives and reducing damage, which can run to the billions of dollars. The path that hurricanes take is strongly influenced by the larger-scale weather patterns around them. We find that small errors in the upper-level flow patterns north of the hurricane appear to have played an important role in the forecast. These errors were present in both the general flow and a wave moving through that flow, resulting in small but significant changes to the forecast path. Understanding the cause of forecast errors is a key step both in improving forecasts and in identifying types of events that are more difficult to forecast.