iPod shuffle and Mac Catalina

mikeasmel69 — sorry Apple caused these problems, and has been utterly unhelpful here in the forums.

My understanding of the situation is that 2nd generation iPod Shuffles are completely unusable under Catalina and its native Music app (which replaced the music part of iTunes). 

However (again, my understanding) the 4th generation iPod Shuffles kind of work. I “fixed” the problem with my 2nd gen by buying a used 4th gen on eBay. Using it is flaky, sync works sometimes not others, will sometimes spuriously complain “this device is not authorized.” I have no way to know if this flakiness is due to Catalina/Music or the “previously owned” iPod.

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 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!)

The best workaround at this time is to use Retroactive to install iTunes 12.9.5 on Catalina.

It seems to work... When you try to synchronise with iTunes ! Even if the tab is blank...

Here's how I've done :

• Connect the iPod Shuffle to your Mac, it will appear in the Finder (Manually manage music seems not working anymore)
• Open iTunes (ah ah ah)
• Create a playlist
• Add music
• Choose your playlist (on the bottom left) - "Fill in from"
• Click : Autofill
• A circle will appear next to your iPod in iTunes and the word "Synchronisation" at the bottom of the left column.
• Wait until the synchronisation complete.
• Et voilà

I can get podcasts onto my ipod shuffle, but they don't necessarily play in the correct order nor does it keep track of where you are in an episode if you sync before completing an episode (either on the ipod or on the Mac).

After reading some of these replies, I rebooted my Mac and it worked.

Make sure you have podcast episodes in the Podcast app.

Open the ipod shuffle in a finder window and click on the Podcast tab to see what is on it. If you are in the middle of an episode it will sometimes give you a check box to keep it loaded on the ipod, but it will revert to the start of the episode. Back in the Podcast app, sometimes the episode will disappear from the Episode list even if not finished (it gets marked as "played" even though it is not done.)

I have reported these issues to Apple several times using the "Report a Concern" feature under the Help tab in the Podcast app.

I am experiencing the same issue but it seems to common to the 2nd generation iPod shuffle but not others. I can see the 2nd generation shuffle in Finder but see no option to load content. The tabs for general, music, podcasts and audiobooks are missing. Also in music there is no content showing even though there is music on my iPod.

I am saying it is common to the 2nd generation because as you can see in the photo the 4th generation shuffle brings up a totally different screen in finder. Notice the tabs are present for general, music, podcasts and audiobooks. The same is true for the 3rd generation iPod nano. The 3rd generation nano was discontinued in September 2008 and my 2nd generation shuffle September 2009. I use a 2009 MacBook to test iPods and I have no issues like this with any iPods I have tested. The problem is with Catalina and the new iTunes and Music.

So my husband spent 3 hours on the phone with Apple support trying to sync his shuffle and finally they told him that Catalina no longer supports the shuffle.

Hello,

iTunes has been retired for Macintosh.

Use the Finder to sync your iPhone, iPad, or iPod with your computer - Apple Support

It works "kind of". You can drag the podcast to your Nano or Shuffle, but it then is listed under songs. Finding it is "interesting" as it is listed alphabetically by the name of the Podcast in the music cue, not in Podcasts.

Yes Apple, please fix this. I have the exact issue as Tammy, I prefer my Nano when exercising or doing things around the house, not my iPhone.

The Podcast app will not detect the shuffle or show any iPods for that matter. You have to open a Finder window and click on the shuffle. It will then look basically like it did in iTunes. I can load podcasts and play them but it is a real pain.

I also was unable to see "Manage Storage". I simply clicked on the Ipod, Removed any old Podcasts, then opened the Podcast App. I then dragged the podcasts to the iPod. Will now test. One note - after I had dragged 3 podcasts, it seem to not want to do anymore. I change the view method to icon rather than list, to make sure I wasn't dragging over podcasts that I had already copied, and this seem to work, Recharging Ipod, then will test

I came here because I too had the same problem but after unsuccessfully looking everywhere for the Autofill section (at the bottom) and the eject button, I noticed that the Autofill section now appears. It is a bit strange but it now shows each and every time I plug my iPod in so all I can say is to continue with your iPod as I have every reason to believe you will be able to fill your iPod as my 1st generation iPod Shuffle is older than yours.

I am using Mac OS 10.15.3 and Music 1.0.3.1 on a 2017 iMac with a 1st generation iPod Shuffle.

Mine is a 2nd Gen. I have always just loaded my subscribed podcasts to it manually in the iTunes window. I drag whichever podcasts I want onto the Shuffle icon in the left pane. I know there are other ways to transfer the podcasts to the device, but this works fine for me.

As for upgrading to Catalina, you will lose the ability to "see" your Shuffle in the Catalina Podcasts app. It appears in the Finder, but there isn't an option to transfer podcasts (and music) to it. At least that has been my and many others' experience. My classic iPod is supported, but the interface is to me extremely frustrating and not worth my time. Finding the Retroactive app was like Christmas....

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