iPod shuffle and Mac Catalina

It seems like you can only add songs through conventional means (open Music -> select device -> select playlist in dropdown menu where it says "autofill from" -> autofill), but I believe I found a way to get podcasts and audiobooks: https://www.simplehelp.net/2019/10/30/how-to-install-itunes-in-macos-catalina/

Thanks for that.

Yesterday, I bit the bullet and upgraded to Catalina & Retroactive with my shuffle Gen 2. So far, so good, but now I have to fix all the other things that are broken like keybindings on my ancient Logitech keyboard as Controllermate isn't supported on Catalina. Sigh...

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.

Hi ShriramK,

Can you kindly post a screen print of what you see with the Shuffle and Finder? I am considering upgrading to Catalina but still haven't decided if it is worth the hassle and risks.

Thanks!

I tried to, but somehow the image I posted in this reply box did not show up on the forum…

BUT: I am no longer sure about this. I have had trouble getting the sync to actually sync. All the functionality appears to be there, buttons press, progress bars move, but…the device doesn't seem to update all that well.

This is of course bitterly disappointing; I held off on Catalina because I felt confident Apple would quietly drop Shuffle support with the Music change. I could have sworn earlier versions of Music on Catalina DID support the Shuffle (my wife upgraded before me and I checked on her machine). Looks like a recent upgrade may have moved the support to the Finder? It's so hard to tell with Apple, of course.

My recommendation for now: if you depend on your Shuffle sync working, do not upgrade to Catalina.

@ShriramK, yes, for the most part, it does work now.

The only non-seamless issue is that occasionally, a podcast won't load onto my iPod when it appears to be loaded in Finder. It seems to happen every couple of weeks.

Otherwise, my 4th gen is working fine. I use it most mornings as I run.

Early on, there were struggles. I think getting used to finding the iPod in Finder was an issue, plus I had two Apple ID/iTunes accounts, which frustrated my ability to load music, etc. One significant issue was, at first, when a Podcast was paused, the software restarted the episode at the beginning of the show; however, the Catalina updates corrected this.

So, it seems that the 4th gen shuffle works and syncs with the Catalina Podcasts or Music app. I have the 2nd gen shuffle and though it shows up in the Finder, it doesn’t show up in the app—-i.e. the bar to choose podcasts, music etc. doesn’t appear. Support for the 2nd gen shuffles has apparently been given the heave ho.

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.

I had a similar experience to that of Qwickening. I have a 2nd generation 2GB iPod Shuffle used primarily to listen to audiobooks downloaded via the public library. Finally updated to Catalina a few days ago and was devastated to learn that there was no way to sync my iPod with downloads on my MacBook Pro! Many hours later, figured out that I can erase all on the iPod by clicking "Restore iPod." Then I was able to drag and drop from downloads (in Finder) to add new audiobooks. BUT THEY DON'T SHOW ON SCREEN! I can verify that they've been added by viewing available GB in Music or Finder, as well as listening, of course. This is a stupid way to have to work it, but at least my iPod isn't trash just yet. QUESTION FOR APPLE: ISN'T THERE A TERMINAL COMMAND THAT WOULD ENABLE SEEING THE CONTENT OF THE IPOD?

I just upgraded to Catalina 10.15.5. I see my iPod device in my finder. The earlier sync problems I reported are gone.

I can also go into Music (the new iTunes) and the device is listed there too. Though the sync operations are no longer there, it does show me an accurate list of all the songs on the iPod.

Essentially, all the music functionality seems to be there and functioning correctly, only split across Finder and Music as opposed to all being lumped into iTunes.

@SaltMarshGirl, sorry to hear the book interface isn't as good. I presume the Books app doesn't show the device? I'm unable to find a terminal command either: I tried to drag the device to the terminal to get macOS to construct a pathname, but all it did was remove the device from Finder entirely, and I had to spend several minutes to figure out how to get it back in there (-:.

But most of all, as @SaltMarshGirl says — the iPod isn't trash yet! Indeed, I've been desperately hoping to change my playlists and can do so now.

@shriramak I have the same issues. The songs and playlists that shows for me to add on the iPod are not all my playlists on “music app” and if I have songs downloaded from the app the system does not let me transfer to the iPod.

Sorry @Raribeiro, I don't know what you mean by "same issues". The point of my posting is that I am not having issues (any longer), at least not that I can discern. I don't know if something changed in the latest 10.15.5 update or not, but in the event it did, I was posting to let other people know that it's something they may want to consider.

Note that I believe this thread is about the iPod Shuffle specifically, not about other models of iPod.

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 !

I was able to open the Podcast app on my Mac, download a podcast, and drag it onto my iPod (after I had opened the iPod from Finder).

I did this several times until I discovered that the podcast was being placed in Songs, not Podcasts

Does this help?

I also notice that when you delete old podcasts using "Manage Memory", that deletions don't appear immediately. In fact, you may have to click "Done" (or even eject the iPod. I can't remember) before you can see the effect of deleting.

Suffice it to say, I am very disappointed in Apple for changing the interface so dramatically, and then making it work (maybe) but incorrectly (and very non-intuitively)

(Vent! Vent!)

Sorry, Becky, but this does nothing. The issue is Apple appears to have completely abandoned support for the Shuffle with Catalina.