iPod shuffle and Mac Catalina

I WORKED IT OUT!!!

Plug your shuffle into your computer, (I have a mac so mot sure if this translates to windows). Open finder and the shuffle should be there in the side bar. Click on it. In the top right hand corner there will be a box that says 'Manage storage', click on that, and then on podcasts in the box that pops up. Now open the podcast app and then drag and drop the required podcasts into the podcast box you just opened in finder! Took me some fiddling around so I hope this work for you too.

All,

I worked with Tammy from Apple's Brisbane office, and we have got a work around.

We have tried it with an individual podcast, and it also worked with a group of 5 podcasts. The steps are:

1. Export the podcast from the Podcast to Desktop (it may work in other areas also)
2. Go to the Music app, and drag the podcasts from the desktop to a podcast playlist.

I, too, found that this page helpful and worked, mostly, for me.

https://support.apple.com/en-us/HT210611

I was still having a quirky bit of trouble when I landed here. My issue was that a podcast episode published at about the same time that I upgraded to Catalina did not show up on my Shuffle (in Finder). So, I deleted the episode in the Podcasts app and re-downloaded it; after the re-download, it immediately showed up in Finder on my Shuffle (and it loaded to my device).

I can get podcasts to work with my iPod on my Mac - Catalina 10.15.1, however, it is a pain.

Prior process on iTunes:

1) Plug in ipod so it can update

2) Eject iPod and go.

New process in Catalina:

1) Plug in iPod.

2) Open finder window

3) Select ipod

4) Resize finder window because it is too small to see the podcast items

5) Select podcasts (don't sync yet)

6) Open Podcast app

7) Refresh podcasts so new ones are loaded

8) Return to finder window

9) Select podcast I want to sync

10) Unclick "Sync Podcasts . . ." to make sure all the old ones ares cleared off, it doesn't always remove old ones

11) Click Remove button

12) Click Apply

13) Click Sync

14) Click "Sync Podcasts . . ."

15) Check to ensure that the correct podcasts are showing up in the finder window(if not, that is a whole other process)

16) Fix any issues with the podcast list

17) Click Apply

18) Click eject

Now at this point the real fun begins because if you were in the middle of a podcast, that location is long gone, it goes back to the beginning Also, if making multiple updates (i.e. several podcasts from several days) there is no guarantee that it will play the oldest first. Which means you can either let it play what ever it wants and fix the problems as mentioned above, or hunt around for it. Note that if you just even start a podcast it gets marked as played and you will have to manually reload it each update.

Bottom line: The way Catalina handles iPods is absolutely horrible (not to mention the number of times my Mac has crashed or rebooted itself).

I was so frustrated by Apple’s dropping of iPod Shuffle support in the Podcast app of Catalina! I have a few 2nd gen shuffles and use them for podcasts. Like others have mentioned I prefer the portability of the Shuffle when I’m out and about to my iPhone or older iPod.

Maybe this has been mentioned in another thread but I heard about the free app Retroactive From GitHub https://github.com/cormiertyshawn895/Retroactive/blob/master/README.md which allows installation of iTunes again, and downloaded it, followed instructions, and presto, I have iTunes back and all my podcasts are there, as well as iPod Shuffle support as before!

So far I’ve had no issues whatsoever on MBP running Catalina, but I no longer have any need for its unwieldy and unsupportive Podcast app. I hope my experience helps others.

At least as of today (May 5, 2020), while Music no longer supports the Shuffle, Finder does. When I click on my Shuffle in Finder I now get almost the same view, except there's also a row near the top that reads

General Music Podcasts Audiobooks

This is now the same sync interface that was previously in iTunes.

because it doesn't care about supporting any product it ever created it no longer sells.

Apple supports products longer than any other vendor -- long past the point that they no longer sell. They stopped selling the shuffle 2 years ago.

I too am a bit annoyed by this, but it's not completely broken yet.

If you have trouble, disconnect, and re-connect. Then go to the General tab and make sure you select "Manually manage music". Then apply right away, and wait for the icon to stop spinning on the left. Then proceed as you normally would.

Also, it can be confusing because Sync is no longer a manual operation. You have to keep an eye on that little icon to make sure you don't disconnect/check until it's done doing its thing.

It's a bug, I've reported it to Apple.

You can drag podcasts from the cache folder to your Shuffle in Finder (~/Library/Group Containers/243LU875E5.groups.com.apple.podcasts) where your podcasts are stored.

To clean up, you need to restore your device.

I was able to access my shuffle and add new podcasts through Finder on my desktop. I had to download the individual podcast episodes through the Podcast app, but then when I clicked on my shuffle in Finder, it opened up with a similar interface as iTunes used to have. It's still super janky and I'm not sure how long it will last, or how well, but at least it's there for now!

For me, the following steps worked - sorta.

First, I didn't have "manage storage" at all when I plugged in my old iPod Shuffle today. (5/6/2020) It's been a few years since I used it, but I wanted to have something to listen to podcasts on at night that wasn't my phone.

In order to get the "manage storage" to show up, I had to click "restore ipod..." and reset my Shuffle completely.

(Note: I had the most recent version of the software already. (1.0.4) But it still didn't show "Manage storage...")

Second, I then clicked on "Manage Storage..." at the top.

This brought down an overlay that showed Songs, Podcasts, Audiobooks in the left nav.

I clicked on Podcasts.

I then opened the Podcasts app in another window and I navigated to the downloaded episodes.

I dragged the episodes one by one into the Shuffle overlay that was already open to Podcasts.

"Nothing" happened. This was weird. And it is STILL WEIRD. Specifically, the Podcasts show the (+) copy icon and the green border when I drag them over, but they don't show up in a list in the overlay. BUT -- I noticed that the purple audio bar on the bottom grew and I noticed that the sync icon showed up in the Finder window behind the overlap next to the IPOD with the icon (not the disk usage one)

So I then dragged a couple more over. I think I dragged about 6 in total. The purple audio bar kept growing. I clicked "Done" and then I ejected the IPOD and yes.... All 6 podcasts were playable on the Shuffle.

That's great, but how do I remove the podcasts in the future? How do I manage this?

Well -- there appears to still be a bug that doesn't show the contents in the overlay (at least for me)

I plan on clicking "restore ipod" to nuke the contents and then carefully dragging them over one at a time. (First episode ends up last in the playlist, FWIW.)

I hope this helps others who have this question, and I hope someone from Apple notices this and addresses the bug in the overlay.

I should add that this is an Orange 2nd Generation 1GB Shuffle.

Take a look at this page. I successfully synced a podcast to my 4th generation iPod shuffle using Finder.

https://support.apple.com/en-us/HT210611

I was having the same issue with my shuffle and ended up on this page hoping for an answer. I watched this youtube video (https://www.youtube.com/watch?v=aybDreAz6Lk), where the person recommends using Terminal and the "killall finder" command in order to display the full finder options. That didn't work for me, so I restarted and reopened finder and was able to see the options to load music and podcasts via finder that I use for my phone.

Hope this helps you.

Kamisue, The iPod shuffle are still plentiful and available for sale on eBay as well as other websites. I have tested the 2nd and 4th generation shuffle and reported the 4th generation works fine using OS Catalina. The 2nd generation has the issue of not being able to seeing the contents in finder and Music. I am hoping Apple will correct this. Compare the two screen shots above, the first being the 2nd generation iPod and the 2nd screen shot is the 4th generation iPod. You can see the tabs for general, music, podcasts and audiobooks are present for the 4th generation iPod shuffle but missing for the 2nd generation iPod shuffle. You can transfer music onto your iPod shuffle by opening music with the iPod shuffle connected and drag the music you want onto it. The other issue I am experiencing with Catalina and the new iTunes format is I am always getting the message; some music could not be copied because this computer is not authorized, which is not true. The work around is to go to the account tab, authorize this computer and sync again. All the selected music will then transfer. It will be on your iPod but not shown in music when selecting the iPod. Again these issues are what I am finding with the new iTunes and Catalina. Older versions of Mac OS and iTunes work just fine with the iPods.

Bit late but for all others who search the same.... I have a solution.

You can't see anything about your iPod Shuffle, not in the finder, on the desktop or the music app BUT, when you create a folder in the Finder, maybe for music, you can drop the music out of the folder on your iPod who is shown as a device in the music app. When you drop the titles on your iPod in the left menu in the music app, you see a little spinning circle. The music app doesn't show title on the device you drop on it but the title are now on your iPod. In the finder under the option, manage memory/storage, for the iPod you can see, that there is space on it in use, these are your music and you can hear it on your iPod.

Thats a ****** way and I am very annoyed with Apple who FOOLED they customers with older but great working products.

Regards !

A quick update... I've still been unsuccessful adding songs to playlists (and modifying songs on playlists) on my shuffle using my Macs (powered by Catalina). However, as another poster suggested, I tried iTunes on a PC, and it worked! Hopefully this bug get's fixed soon as my home and office is 90% apple powered... but having the PC option is a temporary workaround for us shuffle addicts.