The purpose of this study was to determine the observational error of wind reports from aircraft in order to answer two questions: has aircraft wind reporting improved since its introduction and are there certain methods of reporting that prove to be more accurate than others? Data from January of the years 1969, 1974, 1979, 1984, 1989, 1994, and 1999 were analyzed to determine the root mean squared error of data sets that met certain restrictions. Each report originated from N latitude band due to the simple fact that the majority of flights take place over the mid-latitude regions of the Northern Hemisphere. Another test was performed to see the effect on RMSE that would occur if the wind speed of both reports was less than or equal to 50 m/s rather than 20 m/s. A large increase in RMSE occurred in all regions, and when studying the results from 1979 (they were graphed using mean squared error rather than RMSE, which made changes easier to detect), the accuracy was better in the 0-30 latitude range than the other two bands with both the 20 m/s and 50 m/s restrictions. This could be explained by the fact that the regions near the equator lack steering currents as powerful as those in the upper hemispheres, where jet streams dominate the weather pattern. Due to this, data sets between 30 and 90 degrees North could meet the parameters of the study and yet be measuring upper level patterns that are extremely different in two areas. However, between 0 and 30 degrees North this would happen less often and therefore the error from the reports would be relatively lower. Finally, the last test took into consideration the different types of reporting techniques. There are mainly three different types of reporting available for planes to utilize: ACARS and ASDAR, which are automated weather reports, and AIREP reports, which is simply the pilot transmitting data. Data from 1999 was analyzed, and the RMSE of ACARS reports was the lowest of all three. ASDAR reports were close behind in accuracy, while AIREP reports trailed the other two by a considerable amount. There are many explanations for these results, but perhaps that most obvious and is the simple fact that human error was added to the process of relaying the weather data. Thus automated weather reports will most likely continue to be the most accurate and most-widely used source of weather data. This study was supported by a grant from the Simon's Research Program.