I undated my watch to 2.2 and phone to 9.3 and now my contacts on my watch do not show pictures, and all my text only shows phone numbers. I have un paired and repaired the watch, and restarted both my phone and watch with no luck ..
Apple Watch, watchOS 2.2
Some of my photos also disappeared from my Watch when I updated, but I figured out a solution that worked for me. I went into the Contacts app on my Mac and deleted the existing photo, if it showed at all there. Then I re-added it and gave things a few minutes to make their way to iCloud and back to my iPhone and Watch. Now everything is back to normal. Hope that helps!
In that case - and given the other steps that you have already tried - I suggest that you next contact Apple Support, explaining that the issue arose after you updated the software on both devices:
Hi Pete
It may help to follow these steps:
When viewing the time on your watch, swipe up on your watch face > swipe left / right to the Settings Glance > check that this states Connected and shows a green phone icon. Disable Airplane Mode if it is enabled.
When prompted, choose the option to Delete from my iPhone.
I have tried the things that you said. all my contacts are there, just no picture for them on my watch. which is no big deal really, but it also just shows the phone number in my messages on my watch, so if I get a new text and I check it on my watch, I have no idea who it is unless I go to my phone, everything is correct on the phone.
Also the reset sync data button on the phone does nothing.
No Contacts pictures showing on watch, or names in messages
