
(Top Left, phone casual walk no Workout started, top Right, what Watch says happened. Notice how the one is not sharing with the other? Bottom Left, same exact walk but using Workout to track the walk, and see how the Activity app is suddenly populated with info?)
There are issues with tracking, I have run into a major one myself that has the Apple Store stumped.
Here is what I suggest you try to see if it helps...
Take screen shots of all of the data during each of these both on your phone and on your Watch for reference (and to report to Apple as needed).
1. Un-pair and re-pair your Watch to your phone. Let it restore from the saved backup. Try walking a certain distance or route, see what the Watch says and what your iPhone's Activity app says, make note if there's data on one and not on the other.
Then do the same exact distance/route again using the Workout app to start and stop the Activity on the Watch. See what the Watch says and what your iPhone's Activity app says, make note if there's data on one and not on the other.
2. Unpair and re-pair your Watch to your phone. Set it up as a NEW Watch. Try walking a certain distance or route, see what the Watch says and what your iPhone's Activity app says, make note if there's data on one and not on the other.
Then do the same exact distance/route again using the Workout app to start and stop the Activity on the Watch. See what the Watch says and what your iPhone's Activity app says, make note if there's data on one and not on the other.
3. Install a 3rd party app like RunMeter and do the same as above, setting up an exercise and do the same distance/route, and see what it says.
Compare the results of the three.
In my instance, RunMeter is always right and always keeps everything sync'd but Apples apps do not. The Watch does not report ANY data to my phone when I "freeform" walk, vs starting a Workout. I've had my Watch replaced and same problem.
They told me to hope that Watch OS 2 fixes it and if not, they'd return my money since it is not working as advertised.
Their other suggestion was to backup my phone to the iCloud and iTunes. Then:
4. Restore my phone as NEW. Repeat the above 1-3 steps and see if there's any change. If not, restore your phone back to the backup and know you have literally done everything you can and it is their software at fault and not you.
Hope this helps.