The Agony of Syncing Podcasts to an Apple Watch with iTunes Match

Please allow me to vent for just a few minutes.
Yesterday, I wanted to go for a run and listen to a few podcasts along the way. I was going to listen to the latest episodes of Gimlet’s great shows, Start Up and Reply All. Now this would not have been a problem if I was running with my phone, but I wasn’t. I have an iPhone 6 plus and it’s way too big to be lugging around in my small running short pockets so I was just going to be running with my Apple Watch.

There is no native podcast app for the Apple Watch1, and since third-party apps can’t run on the Watch without the phone nearby, Overcast won’t work for this situation. “No problem,” I thought. iDownloadBlog ran this piece on how get podcasts in an iTunes playlist and sync them to the Watch. Their solution is not ideal, but it’s not so much work that I can’t do it every few days.

I learned that their solution only works if you do not have iTunes Match activated on your phone. I do have iTunes Match, so here’s the process you have to go through to get podcasts on the Apple Watch through iTunes Match.

1. Download podcast through the web – 1 minute

This one is easy. I went to each podcast’s site and downloaded the latest episodes.

2. Import podcast MP3s into iTunes – 30 seconds

Again, so far so good.

3. Convert podcasts to AAC files – 2 minutes

The first problem you run into is that since the podcast episodes are marked as podcasts in their metadata, iTunes (intelligently) does not upload them to your online library like it would a new song in your library. I tried changing the metadata in iTunes and ID3 Editor, but iTunes wasn’t fooled. Simply right clicking on the tracks and saying “convert to AAC” works every time though.

My rage meter is still very low.

4. Add episodes to a playlist and upload to iTunes Match – 5-10 minutes

Now that your files are converted, you need to drag them into a playlist (mine is called “Podcasts” and only holds these 2 episodes). Then you wait for iTunes to upload these files. This can take a long time if you don’t do anything, but you can speed up the process a little by right clicking your episodes and selecting “Add to iCloud.”

This takes a while, as you can’t simply upload these two files. Oh no! iTunes will refresh your entire iTunes Match data, which takes a few minutes. So you wait…

Rage meter is starting to tick up just a bit. This is becoming quite the ordeal.

5. Download the playlist to your iPhone – 3 minutes

Once your files are safely in the cloud, you need to switch over to your phone and download your playlist with the podcasts to your iPhone. You need to do this because the Apple Watch downloads the playlist from your phone, not from iTunes Match.

This should be easy, but sometimes there is a delay in when your computer says your playlist is updated and when your iPhone notices the change. I had to force-quit the Music app on my phone a few times to get it to manually sync with the server, but my new playlist did eventually show up.

6. Start charging your Apple Watch – 1 minute

You can sync one playlist to your Apple Watch, but it will not do it unless your Watch is charging. Fine, I put my Watch on the charger.

7. Sync the playlist from the iPhone to the Apple Watch – 10 minutes-****ing forever

Go into the Apple Watch app on the iPhone and navigate to Music>Synced Playlist and choose the playlist to sync. Syncing will happen either slowly, or infuriatingly slowly.

My 2 episodes amounted to just over 50MB, but they took almost 15 full minutes to sync. The progress bar in the app is almost useless, as it shows 4 statuses:

  • Sync pending
  • 1% complete
  • 99% complete
  • Synced

So basically, it says “1% complete” for the entire sync and then is suddenly done. This is crazy, and the whole syncing process is way longer than you would think it would be considering these devices could use WiFi to transfer the files in a few seconds.

Rage level has maxed out, and I’m just rage-playing Desert Golfing while I sit there in my workout clothes, losing all desire to run at all.

Total time = 27 minutes

That’s an obscenely long time to do something that should be very simple. I know, I know, I know, this is a 1.0 product and I am an early adopter so problems like this shouldn’t surprise me. However, as an early adopter, this is also my chance to vent my frustrations so Apple can address these issues before the Apple Watch is really a mainstream hit.

By the time the second season of Serial starts and regular people start listening in mass, this can’t still be the solution. Apple, if you’re reading this, please fix podcasts on the Apple Watch!

  1. An odd omission, especially considering how many people started to listen to podcasts in the past 8 months. Podcast listening has to be one of the expected use cases of the Apple Watch.