I have the Garmin Forerunner 220. Software version 2.20. says software is up to date but show the current software as 2.20. I am using the Garmin Express to up date. My runs will not transfer to Garmin Connect as well.
We have confirmed this is an issue with the 3.2.8 version of Express on the Mac only. To workaround this issue for now please use WebUpdater to update the software on the Forerunner 220.