Had to correct this:
I have always had my watch download to MapMyRun (MapMyFitness) and Strava. Then it automatically uploads from MapMyFitness to CityStrides. I like this setup because I feel like it gives me two locations where my running history resides. If something happens to Strava then my running log is on MapMyFitness and visa versa. I seem to have less issues with my data appearing on CityStrides In a timely manner with this setup.