I was having the same issues with my series 3 Nike Apple I watch. I had tried everything on this forum and nothing helped. Then I read where someone had deleted the iwatch app from their phone, hard reset the watch and their phone, then manually paired their watch. It worked! I Upvote Ashton_C This worked for me on apple watch series 5 iphone xs max ios 14 So, do this: —Delete the iwatch app —Restart apple watch —Make sure your phone is still connected to wifi —re-download the iwatch app —when pairing your phone and watch, MAKE SURE to press MANUAL on the iphone apple watch app!! Then, you’ll be able to download the needed software to proceed!