iPod shuffle and Mac Catalina

I had my apple shuffle for swimming for over 6 years and I love it. But $235 for it!

I think I paid 114.95 for it from Waterfi.

Although the podcast app does not detect the shuffle, I noticed that iTunes detects my ipod shuffle and I can drug the podcast from the podcast app to the iTunes app. It will be added as a song, though.

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'm glad I checked before "upgrading" to Catalina. I use my shuffle for podcasts at the gym and literally would not keep up my routine without it. Have survived all the "improvements" to itunes over the years with workarounds, and will just hold steady for now until I'm confident my equipment can actually serve my needs going forward.

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.

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 am deeply angry that apple released this upgrade without adequately supporting ipod shuffle (my waterproofed, apple certified shuffle for swimming) and ipod nano 8th gen for podcasts. I finally figured out the laborious and time consuming way to put podcasts on but can't get a playlist on my nano. You may be the dominant player now but moves like this create the perfect storm for users to look for a disintermediating alternative to apple. Someone will break your near monoply some day - why hasten the fall?

I really really dislike that they discontinued the shuffle and support for it. So in hopes that someone reads this and maybe reconsiders, I just have to say the shuffle was awesome for so many things--my kids all have one, that way they can make their own playlists that they can listen to while doing chores, riding the bus to meets (no need for teachers to have to confiscate them at night--we live in the middle of nowhere and some games require overnight hotel stays due to 7-8 hr driving distances), etc and it's inexpensive enough that I don't mind if they get lost or broken. Also, my kids don't have phones or any internet connected devices and I don't want them to! (I know that won't last once they hit high school, but for now I can still enforce that.) And I take a shuffle and speaker to work to play music from--that way I'm not worried about it being stolen and if I'm somewhere else in the building besides the main desk, I haven't left my phone behind. I can still connect it on my kids' ancient iMac, but super annoying that I can't do it on my own anymore.

Darkglass, Why not buy an inexpensive previously used one and test it. Unless you are a collector and plan to hang onto it and not use it you will overpay for a factory sealed one. Just because it is factory sealed doesn't mean the battery will still work.

iPod shuffle will not sync audiobooks at all with Catalina; and the workaround for syncing podcasts is absurd. I have no idea about syncing tunes, but basically Apple said goodbye to the iPod when it rolled out Catalina. My solution to the situation is to keep an old laptop with the old operating system on it... Just for the sole purpose of syncing spoken word content onto my iPod shuffle. Keep waiting for a bug fix from the brainiacs at headquarters, but, oh well... guess not.

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.

I sure hope so as this has been an issue since Catalina and the new iTunes/music were released. I have reported this issue by phone to tech support as well as online directly to them. I have been able to work around this but it shouldn't be this way. Every time I try to sync and add new music to any of my iPods I get the message that some music was not added because I am not authorized on this computer, even though I am. I have to reauthorize my computer every time and then it will sync completely. I have done this over and over. I have another computer with an older OS and the last version of iTunes before Catalina and it works perfect without issues as it always did.

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.

So after reading this...if I want to use a 4th generation ipod shuffle using Catalina, is there a way to load music and/or podcasts and if so how?

Also, I haven't yet upgraded from High Sierra to Catalina. Should I?

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....

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.