First of all, Cumulus does not send max wind speed or max wind gust at all to WU, as those are not part of the protocol, see
http://wiki.wunderground.com/index.php/ ... d_Protocol
WU determines the max values itself from the individual values submitted.
Here are the parameters concerning wind/gust speed in the protocol, and what Cumulus sends for each, while running 'live':
windspeedmph - [mph instantaneous wind speed]
By default, it sends the last 3-second wind speed from the console. There is an option "Send average wind" in the WU settings in Cumulus, setting this causes the average speed to be sent instead (this is not normally useful for Davis stations).
windgustmph - [mph current wind gust, using software specific time period]
Cumulus sends the peak gust over the last 10 minutes.
windspdmph_avg2m - [mph 2 minute average wind speed mph]
Cumulus send the average wind speed (normally 10 minutes)
windgustmph_10m - [mph past 10 minutes wind gust mph ]
Cumulus does not actually send this, I believe that it was not part of the protocol when I wrote the code.
While Cumulus is sending archive data to WU as part of the 'catch up' when it first starts, the only wind speeds available to it are the peak speed for the archive interval, and the average speed for the interval. In that case, it uses the peak speed for the interval where running live it would use the latest 3-second wind speed (so that the peak value is not lost) - so that value will get sent to WU as 'windspeedmph'. The peak value of those over the last 10 minutes gets sent as 'windgustmph'.
So if you are using archive data significantly (i.e whether you shut down Cumulus for extended periods), what your station's logger interval is, whether your peak speeds occur during the times that Cumulus wasn't running, and exactly how WU do their calculations, your WU high wind speed could come out close to your WU high wind gust. Whether or not you are using 'rapid fire' will also affect the WU calculations compared to the data shown in the table, while Cumulus is running with live data (not every set of data sent appears in the graph or table, but presumably WU do use every set to determine max wind speed and gust).