I took my phone on a run today. I did what I usually do: started a previously downloaded playlist on Apple Music on the watch then started the workout, just took my phone with me without messing with it.
First segment ended, voice feedback triggered and it worked, BUT the song playing stopped completely (this is an issue reported by other people on reddit). I manually resumed playback.
Second segment ended, voice feedback played and the media playing didn't stop this time, just going down in volume as usual. BUT after the song ended the next one didn't play. This persisted the whole run, so I had to manually resume media playback after each track.
After running I started a walking workout to cooldown, took my phone out and started playing from Apple Music through the phone. With this setup I realized that voice feedback still worked and I didn't have issues with media playback. I'm not sure how other headphones would handle this, I have AirPods Pro 2.
I had this exact problem with media not playing on my very first run on watchOS 26 so it's probably not a one-off occurence.
TL;DR:
What I found the most reliable way to have voice feedback and consistent media playback on a wi-fi only watch:
- Take your phone with you, voice feedback only works if the watch is online;
- If you're on Apple Music and have AirPods, play music through your phone, not your watch. AirPods Pro should handle playing music from phone and voice feedback from watch simultaneosly;
- Start workout normally on your watch.
This release is really disappointing. I've been struggling with watchOS 26 for two weeks and now need a whole elaborate setup to do something that previously just worked. Apple was so focused on this phone / AI slop integration that they riddled watchOS with bugs.