iPod shuffle and Mac Catalina

(Very) Long time Apple loyalist and user. Very disappointed to discover that my expensive new MacBook Pro with the latest version of IOS no longer works with my shuffle. I now regret my MacBook purchase. I will have to think very carefully about where I go from now on with future upgrades. Paying a premium for Apple is all very well but not when this sort of thing happens.

I have now spoken with three regular technicians and a senior technician twice, with a scheduled phone call again in two days. I have supplied Apple with screen shots of my Mac, showing what happens when my Ipod shuffle is hooked into the Mac and it not being recognized. Apparently, the screen shot files have been given to an Apple engineer to try and find out why the Ipod shuffle is not working with the Catalina software. This is a huge mess! I have spent way too much of my time trying to get this fixed. Fortunately, I have a Mac laptop that does not have the Catalina software installed yet--I will not be updating it!! It is just wrong for Apple to release these new operating system updates without adequately testing them. If the Ipod will not work with the new software, Apple needs to refund all the customers who had purchased them and now cannot use them with Catalina.

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.

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.

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.

I have the same problem (as well as not being able to use any Windows programs). Blaming it on an Apple cable cable is really dismissive of the user. My iPod is effectively useless, as is iTunes and Music.

Catalina made nothing better, rather it created a ton of headaches. My God I wish I hadn't been so stupid to trust Apple and install the update.

Did anyone ask a user what was important?

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.

That's more than a bug. I can't find the "cache" you refer to tp be able to drag anything to my Nano (not shuffle) and to have to wipe the device every time you update renders it useless (like my office files).

My goodness I wish I hadn't been so stupid to update my computer

Apple created a wonderful, affordable product in the iPod Shuffle. Small, compact but with great sound. I've used it for years. Suddenly, they update the OS and it no longer supports the product. You can see it, but it's not possible to see playlists or move recently added songs to the Shuffle. Apple is 'upgrading' products to delete access to earlier products as a matter of course. Apple, please provide an update to iTunes music and podcasts to allow them to be backward compatible to iPod Shuffle.

Thank you all so much for posting! This is my first time posting anything and I am compelled to do so because I tried to manually manage my iPod shuffle content today, only to discover that my newly downloaded Catalina had stopped supporting it. I love listening to audiobooks on my shuffle and cannot believe that Apple would be so obtuse as to stop supporting such a great product. I love working out with it because you don’t have to look at it to pause it, you can clip it onto your shirt, and it weighs almost nothing. I do NOT want to carry around my iPhone. I also listen in my car and love the fact that I can pause it when I get in traffic and not take my eyes off the road. Please tell me that someone in Apple is reading this string and will modify Catalina to allow faithful Apple users like us to use the shuffle again. I have been a loyal Apple user since 2005 but their failure to understand customer desires in this case is bad form and causes me to question my continued loyalty. Please fix this!

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.

Right with you, AlexAppleUser: the Shuffle is perfect for books, and fiddling with them on an iPhone in the car is just plain dangerous. I hope Apple is paying attention to our frustrated cries for help.

After upgrading to Catalina, my various Shuffles were simply not recognized in Music or on my MacBook, so the Podcast drag-and-drop work-arounds I read about here can't work for me. All kinds of checking gave no fixes, so I backtracked to Mojave. (A saga in itself: Time machine bombed, but luckily I had a Carbon Clone Copier image from May; at least I have my books-on-Shuffle back, even if I lost some files in between.)

Apple's bland "try this, try that" answers are simply not helpful. I would like the issue to be acknowledged, even if there is no fix right away. Failing that, my long-time trust in Apple - also since 2005, as it happens - remains badly damaged. I am already spreading warnings to think twice about accepting upgrades unquestioningly, and if there is no resolution in this case, in effect abandoning loyal users unwarned, I shall be tempted to go back to Windows.

My issue is when I listen to a podcast on my Shuffle and then decide to listen to music, I pause the podcast, go over to music, but when I come back to the podcast, it goes back to the beginning of the episode rather than picking up where I paused. Anyone else have this problem?

I've also tried to look at my music list and nothing at all comes up. I can see my shuffle device in both the finder and music, but it is as if it was blank and useless - no way to move the music or eave know what I have. I can still listen to it just fine. Zero customer service score for this boneheaded move.

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.