iPod shuffle and Mac Catalina

Hello Robert-D2,

Welcome to the Apple Support Communities.It appears the iPod Shuffle is not showing the option to sync podcasts. I'll help in any way I can.

Here are some suggestions:

• Restart your Mac if you haven't already from the Apple () menu then Restart.
• Check syncing in safe mode: Use safe mode to isolate issues with your Mac
• Use a different cable and/or USB port and try these: Use the Finder to sync your iPhone, iPad, or iPod with your computer

Thanks and have a great day.

@UABKirksville - I'm sure you're correct in this and it's really annoying.

I realise that Apple want to keep moving forward with their App interfaces etc, but there's something gloriously simple about the shuffle and the ability to create a little podcast playlist was key to my using it. I have managed to get a single podcast onto it so far, but it failed to sync two I'd tagged (maybe you need to sync for every episode of different podcasts...), and has kind of spoiled how I use the shuffle. Boo, Apple...

Becky,

I need to have a problem with my iPad shuffle and spent one hour and 41 today with Apple support. No resolution occurred and the three technicians I spoke to had no clue why this was happening (after being on the phone for 1 hr. 43 min.) I can’t even get my shuffle to be recognized by my desktop Mac. I attempted again to call back Apple support but had endless wait times and the automated system to call me back kept coming up with errors. If Apple had made it clear that updating to Catalina OS would have resulted in my shuffle not being able to be updated, I would have never updated the software. In addition, I have apps on my desktop that now don’t work because Catalina does not support them. It is incredibly frustrating. Apple should have never released this operating system without fully testing it.

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, 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).

Here is my workflow:

1. Use Podcasts app for podcasts, Music for music, and Books for audio books. Have your favorites ready to go.
2. Plug in your 4th Gen iPod.
3. Open Finder and click on your iPod.
4. In the iPod menu select your favorite music, podcasts and books (I've gotten all to load in Catalina for my 4th gen). You can click on Music etc. at the top to organize your selections.
5. Make sure you "sync," or else your favorite may not be there.

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.

Mine just shows this blank page. I've been having issues with every possible aspect of my Mac since the update. Magic Mouse, Wacom Tablet, Safari, iPod Shuffle, etc...

Sometimes I wish Catalina OS was a person, so I could kick him repeatedly his dumb face.

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.

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.

I have had a similar issue. I just plugged in my iPod shuffle to add a few songs I just downloaded from iTunes... and the Music App doesn't recognize my playlists. When I click on my iPod Shuffle, I receive the message... "couldn't communicate with a helper application".

When I connect my shuffle to the desktop mac, I keep getting an error message "The selected device could not be found". I spoke with a senior tech at Apple support today. He was baffled and had me supply files and screen shots from the podcast, music and finder apps to provide to Apple engineers. I will be following up with him on 11/20/19 to find out what the engineers have found. I never had any problems with my 3rd generation iPod shuffle prior to the Catalina OS download. It is very frustrating! Also, be warned that any 32 bit software will not work with the Catalina OS.

Yeah, that doesn't help. The shuffle shows up in the finder, but it still won't let me sync the podcasts I want to sync. I've selected the specific shows, told it new episodes only, even created a station that I asked the shuffle to only sync from. It still doesn't sync correctly. .Sometimes, it won't sync anything. Other times. it just randomly chooses podcasts that I didn't select at all. Still others it selects episodes I played weeks ago, can't even find in the podcast app, yet they show up on the shuffle.

When the "Manage Content" button does appear in the Finder window, which is rare, I can finally see everything that's supposedly on the Shuffle, and it's random as ****. It says I deleted it, then that same content gets restored to the shuffle when I click Sync. It's a mess. Apple created this disaster, frankly, because it doesn't care about supporting any product it ever created it no longer sells.

Sadly, I think it is now evident that Apple has abandoned the Shuffle and the Nano with its release of Catalina. It’s hugely frustrating and a bit mean, I think. The Shuffle remains by far the best ‘tiny’ MP3 player for sport etc. So much so that I have a brand new one in my drawer purchased from eBay, specifically to use only when my current one stops working. So, this unused player will likely never be used. Poor show, Apple. Retaining some software that allowed us to continue to use Apple branded products that we’d bought from them would have been better customer service and likely very little extra work for their massive team...hugely disappointing...

I’m not sure if things are still ok for the Shuffle with iTunes on a PC, but the fact remains that the APPLE iPod Shuffle doesn’t work on an APPLE computer using APPLE music!!! Which is not acceptable!!!!!