Getting my Mac unplayed podcasts on my Apple Watch

Mar 13, 2016
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It isn't obvious where to post this.

I want to know how to tell my Catalina's Podcast app to load "Listen Now" (or any other selected) podcasts on my Apple Watch.

I do a walk regimen where I like to listen to podcasts. I look at my podcasts on my Catalina Podcast app and see episodes in "Listen Now".

When I take my walk, sometimes I find a partial episode on my Apple Watch. When this happens, I can often finish it later. Or I can try to play it on my Mac, but my Mac doesn't know where I left out. I mark some old episodes as unplayed on my Mac and maybe in a couple of days, they show up on my watch. My watch lists lots and lots and lots of episodes, but those are apparently just titles, they can't be found. Often I can't find any unplayed "Listen Now" apps on my watch.

For the last week, I haven't been able to play any podcasts on my watch. For the last couple of days, I also can't play if I try using my iPhone. In both cases, I get the message "Unable to Play". Something went wrong. Try again later. I powered down both devices, then powered on my iPhone, then powered on my Apple Watch, and after searching for my AirPods, was working again.

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