I've seen that message maybe 5 times in 4 years of Wahoo Elemnt use. Every time except one it was just an intermittent thing - try again later and it worked fine. Between your wireless, Wahoo, Strava and the cloud services they use, there is always the chance of a hiccup - just like the rest of the Internet.
That one time, I contacted Wahoo and they had pushed out a bad update - they released a fixed version and all was good.