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On the Strava Settings page if you go all the way down they mention "Occasionally you may need to refresh your connection with Strava and myWindsock." and there is a Refresh Connection button, which should fix your problems.

You have to do that once in a while or reconnect when you go to the website if it shows the Strava button.

Unfortunately, this is just the way it works - I work with various API's (Application Programming Interface) for web development and this is just a fact of life now because companies are continually updating their security protocols so when a company like Strava updates their security protocols having to do with how external sites integrate into it; you have to re-authenticate your account connections between the two sites.

Are you guys still getting WindSock reports from your Strava rides? I used to get them all the time but then they suddenly quit and I haven't seen one in over a year.
 
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