Will it Sync? The Original iPod and macOS Catalina 

As an engineer myself I simply love the backwards compatiblity that Apple provides for their products. Not only this example with 18 years old MP3 player, but also with most of their accessories (like iOS and MacOS support of 6+ year old iPhones and computers, TimeCapsules, Airport base stations and such). This type of long-term support is extremely rearly seen even in the industrial electronics and servers, let alone in the consumer devices.

Love how the orignal iPod's image on the sync page still matches - down to the Firewire logo!

Now let’s try connecting the Newton.

That's so awesome to find people interested in old iPods and "local music" in general. During this hype of music streaming services and products wiht short-life cycles, people forgot how brilliant were this little iPods. And more important: people forgot how to really own music libraries. With Spotify/Apple Music you just rent it and it's not the same feeling. Great video by the way!

I'm impressed the mega-dongle to FW400 works! The iPod Mini remains my favorite iPod for sentimental reasons, although the fat Nano was neat as well.

Unfortunately they didn’t always keep supporting the original iPod. About 8 years ago I bought an original iPod and it wouldn’t sync because iTunes didn’t support it. I even went to an  store and confirmed it wasn’t supported. About three years ago they reininitiated sync for older iPods. I am glad they kept it in Catalina

I still regularly use a 60GB iPod Photo for music. I collect CDs, and ripping them to an iPod just feels right and it sounds great. Watching and writing this on my iPad 2.

Still use my IPod Classic daily on our Bose speaker dock as the house music over dinner. My husband cracked it open, put a new battery in it and a bigger SD hard drive. It has had it's troubles, but it has ten more years of life in it. Go Classic!

*has a music library* *1 artist* *U2* You glorious sonofagun. It's Songs of Innocence isn't it?

I LOVE my old iPod Classic! Up until today, I thought I could never update it again. Bro, you have just SAVED ME!!!! Thank you so much for the info!

So happy to see this! I have a 3rd gen iPod touch that's still alive somehow and it still has room for music and audiobooks.

I still use a bunch of different iPods as a daily car music player, when I go on walks, and for speakers around the house sometimes! I have over a dozen different models, and I like the 6th gen classic a lot for its small clip, and my larger iPod is a 64 GB SD card 4th gen iPod photo (was originally 20 GB until it died). My first iPod was the first gen iPod shuffle, and I used it all the time until the headphone jack started to wear out and the USB connector came loose from the rest of the iPod. I try to give them all love evenly, but I can only listen to music on one at a time! :)

I have been trying to connect my 2nd gen. iPod Shuffle. I can see the iPod, but I can't load any podcasts on it, not even Connected. From my research on Apple support communities, it looks like I'm out of luck.

The one thing that sucks with Catalina and trying to use a Ipod classic is you are not able to manually place songs into playlists anymore. like there is no way to do that :/

That little iPod 1st Gen is older than me (by one year) and it still works so well in 2020 - super nice to see the consistency in compatibility with these things nowadays!

Great video! Nice to see them all being still supported. I had an iPod Nano in Red (2nd generation I believe) - 4GB? I just loved the colour so much. I then went onto owning an iPod Touch so didn't feel the need for a iPod Nano. Eventually replacing them both with an iPhone. I'm still very fond of those the red iPods and always still tempted to get one back!

My favorite iPod is the 6th gen iPod Nano. It has a clip so you can attach it to clothing. It has a built in radio so you can listen to FM Radio. I still use mine a lot. Oh.. and you can record audio with it as well. Super cute with the various clock faces available. I still have the band to wear it as a watch. The day they discontinued them I bought one that is still in original packaging in a drawer so I can pull it out when my current one dies.

Thanks! Great news. Have a classic iPod that still functions perfectly with a Yamaha compact stereo system & I also run it through a tube headphone amp and bring on trips when I want to chill without a phone.

BS Syncing is a pain In Catalina. You can't just update your iPod. You gotta sync your whole collection every single time. And the Music app gets super weird when just dropping a few songs from the "Manually Update this iPod" tab.

I remember that U2 album.... for the wrong reasons

Great video! I love re-visiting iPods. My first was a 4th Gen iPod Nano. It was amazing but I quickly upgraded to a 2nd Gen iPod Touch. I had the 2nd Gen shuffle too. I forgot about that dock it came with! I loved seeing that.

I still use my iPod Classic 120GB for a variety of reasons... 1.With my Altec Lansing inMotion iM7 from 2005 with gorgeous sound (permanently set up in dining room cuz it's a beast) 2. Bedside with my SoundFreaq, which also has great sound 3. Due to security reasons, at work. 4. Extra Extra back-up of ripped CDs that are not available anywhere but in my collection

GMM should get you on their show for a new series: Will it Sync?

I have one of those iPod Classics like you do Stephen. Where do I get the replacement batteries from and is it a relatively easy swapout?

I use my 160G iPod everyday. I can't stand having music play from a phone and get interrupted by calls and messages :) Hook that iPod up to the stereo while my phone is still in my pocket and keep those jams booming! But when I want to play my iPod on my computer, yes, the Music app on Catalina recognizes my iPod, but it doesn't recognize any of my playlists on the iPod. And the sorting is messed up too. If I sort all my songs by "Artist", yes, the artists will be in alphabetical order, and their albums will be in alphabetical order, but the songs of their albums will also be in alphabetical order instead of in their actual track listing order. For example, the first track on The Beatle's album, Please Please Me, is I Saw Her Standing There, but because it starts with an I, it shows up in the middle of the album. I hope they fix it, because right now, I really hate the Music app, and iTunes won't work on Catalina :(

Good to know I can still use my 5th Generation iPod. Now I just gotta break out the iDog and Ill feel like im back in 2005!

i collect apple computers, cool to see other people do so too!

Man spends entire savings on dongles circa 2019

But how do you put your music from your Ipod Classic onto a new Mac Mini running Catalina?

Dude, that original IPOD is cool. I wish I still had mine.

To clarify, the only music that syncs to the older iPods is music that you purchased from iTunes / Apple Music store, ripped from CD, or downloaded or obtained from 3rd parties, correct? It's my understanding that songs in your Apple Music iCloud library (for example, the new Kanye album that I've liked and had downloaded to my iPhone X) will NOT sync over to my 3rd gen iPod, right?

Its amazing Apple still supports 18 year old devices!

It doesn't give you a list of the albums by artist. So if you have 20 'Greatest hits' albums, it's a complete gamble as to whether you get the one you actually want to listen to. Highly annoying.

Yes! I still use my 80 GB iPod Classic on a near daily basis for music on my home audio system and also for long car rides for creating playlists, although I am completely aware that my 256 GB iPhone can store this entire selection with room to spare. Redundancy *feels* comforting, as does nostalgia. Thanks for the demonstration! Also, I echo the sentiments of Arturs Savickis (previous commenter) in Apple's dedication to backward compatibility with their older peripheral devices.

Thank you very much for reassuring me as I'm about to go for Catalina, but I want to be able to sync my iPod Classic.

I can sync my iPod Classic with Catalina after factory resetting it. But after a few syncs I have to reset it again. Is there a fix for this or even a iTunes alternative for syncing my Classic?

Considering it still syncs my 6th gen nano and my Razr V3im I‘d say yeah, they probably got their bases covered

Will an Ipod 4th generation still work ? I bought a Sharper Image VW recently & it won't work with the 5th Generation or later devices because of the cable. I hate it when they upgrade and older stuff won't work. Thanks for doing these tests. I never heard of you before but I am very much into retro Macs and I am envious of your Mac collection. My first Imac was a used Mac original with gray screen ( I can't remember what it was called ), then a black very old Mac Book and then a Performa 550 I bought at a garage sale for $50. I once had 22 Macs and wish I had been able to keep them but I ran out of room. I have the pink Ipod shuffle but can't seem to get it to charge anymore. I subscribed.

I really like your videos.. id say by the back ground you are an Apple collector.. yes I still use an iPod, iPod mini to be exact. I get a lot of people asking when out in public. keep up the good work.

HI ! Ok it's a cool fact that you still sync your Music, Podcasts, etc... On your iPod Classic.. But what about the old functions like contacts, calendars and others stuff ?? For example when my iPhone run out of battery, my iPod classic used to be my contact book, I could use it to ask a friend's phone and make my call.. Seems it's time to say goodbye :(

Still using iPod 160GB daily. One huge drawback to Catalina is that it takes all podcast mp3 files, strips them from the named folders and gives them alphanumeric mp3 names that do not identify the original mp3 names. Makes organization of podcast files I want to keep permanently impossible. This is unacceptable to me. I reinstalled Mojave, then restored to my last backup.

That is a fine video. My only iPod is a silver mini, which I have not yet tried on Catalina. I think I tried my iPhone 3GS since I got Catalina, and it still works. My oldest Mac is my Quadra 700, but it does not work with any of my iPods or iPhones.

If you have your original iMac software, somewhere in the upgrade path on the installation CDs somewhere back around Jaguar or Panther (Tiger?), on one of the discs or on a disc by itself (with iMovie installation I imagine), there's an iMovie (is that what it was called back then?) tutorial with a person walking around the outside of a house recording video. Let me know if I'm crazy thinking I remember that when they get around the house to the side window (toward the end of the video I think) there can be heard in the video the sounds of some adult activities coming from inside. If i'm correct, it seems like a piece of history that should be preserved...

Thanks for this video! Do you know if the iPod classic click wheel sync with the new mac OS Ventura?

Do you know if the first gen ipod shuffle will work on the new itunes?

I use my 160gb iPod classic all the time. Will be a sad day when it dies. Only thing I wish it had was bluetooth to use my airpods with

I’m looking at getting the iPod Classic 3rd gen and I’m curious if you have any tips? I want this particular model because I could not afford one back when I first saw it. I still think this one is such a slick design. Anyway, the main question I have is if I buy one (eBay) and need to replace the battery, is that something the Apple stores will do, as a service, or would I have to find someone who offers vintage iPod battery replacement services? Also, are the batteries even replaceable (are batteries still manufactured for the 3rd gen)? Thanks a bunch.

Wow, man. Thank you so much. I was able to sync my old iPod classic via Finder in Catalina eg it wasn't showing up in "Music".

How do I recover music off iPod classic to iPhone 12??? Any help

I just bought a 7th gen nano, coz I live in 2010, but I do not regret it at all and it's a great little music player!

I’m still using a 2008 AirPort Extreme to host my Catalina time machine backups

My iMac is on Catalina, my 4th gen iPod Touch on iOS 6 doesn’t work with it. I had almost 64gb of audio on it, I wanted to add 4 new songs to my iPod which I’d downloaded on the latest version of the Music/iTunes app. They would not drag and drop. The settings for manually mange music which I usually had ticked were defaulted to off, everything was defaulted to off. I tried re checking the relevant boxes to allow the devices to sync and dragged and dropped, but no. It didn’t work. It wiped my content from my iPod and added the new tracks. 64gb of library wiped from my iPod. I ended up re syncing my entire library from scratch, which worked. However I wanted to find a way of dragging new music and playlists over as and when I need to. It won’t do it, it hangs up and constantly loses half of the data from the iPod. I finally thought I had it all synced across for the second time, only to find when trying to play random songs from my library, some of the files were corrupt and it skipped to the next track. If you only want to sync a couple of small files, it will probably work. If you want to keep an extensive library on your iPod and add to it as and when it won’t. As for Catalina, it’s garbage. The amount of album artwork which didn’t come back after updating to it is ridiculous. The whole navigation of it isn’t as intuitive as what has been previously. My iMac runs slower with every new OS release. With Apple Music they are pushing the consumer into streaming, it’s becoming more difficult to purchase, download, organise and listen to my music library they way I want. I used to love Apple, I have an iMac, iPhone, iPad, iPad mini, several iPod Touch models. They used to be fantastic, as time goes by they are becoming glitchy, their updates are not refined and seldom offer any actual improvements. I’m seeing more and more how they are trying to make me use the products how they want me to, not how I want to. I actually spoke with the Apple help dept over the phone to try getting my iPod working, they told me iOS 6 is not compatible. The best I can hope to achieve is to reinstall my library and just leave it alone. Adding new content isn’t viable. So now what buy a more up to date device at a significant expense? I hate the digital, tech driven disposable age.

Question - iPod classic plugged in (Mac desktop - Catalina) immediately shows the iPod but on the right shows "Software: Loading" not the screen yours shows with the menu. I've waited a full 24 hours with the "software: loading" screen. Suggestions?

It is good to know that my original iPod from November 2001 will work with Catalina!

If ONLY we could get a 64-Bit iDVD update so it can run on Catalina. There is no other software as good as iDVD for authoring DVDs.

I still sync songs to my 160gb iPod classic, got it for 7th birthday, those days ;)

i still use my ipod classic. lol i refuse to update my iTunes on my window computer. still adding more music.

Great news that I can sync my iPod classic to Catalina. My question is which cable do you use, or adaptor? Its got to be a 30-pin to thunderbolt for my MacBook Pro. Hard to find the info. thanks.

Man!! I can’t get any of my downloaded iTunes from my MacBook to sync to my 5th generation iPod. It says sync completed but there’s no songs in my library

The last Apple product that I used was the iPod touch 4th generation. I haven't used an Apple product since. It is awesome to see Apple still supporting old hardware.

My first iPod was a mini (in 2005) which was part of a college offer with an iBook G4...

I can Sync my iPod Classic but how do I play the tracks of it while it is connected... Music won't let me do it.

Thanks, I was worried I wouldn't be able to sync my iPod if I upgraded.

Thanks for the encouragement. I was able to sync my ipod mini !

I have a MacBook air & an 80GB iPod classic. My cord doesn’t fit with my MacBook Air? Which cord are you using that’s compatible?

Does it support the hp edition iPod or was that a separate software than iTunes ?

i have Catalina 10.15.6 and am trying to use iPod classic does not show like your iPod shuffle ? What can i do ?

10.12 or newest it can't drag & drop or make a playlist via finder, but 10.11 captitan can do it in itunes, i love itunes

What about the playlists on my older iTunes (OSX Mojave)? Will I still be able to create playlists, sync old playlists and do everything like old days?

I have a 5th Generation iPod and also running Big Sur ver 11.5.2; and I can no longer sync music from my iTunes account onto the iPod. Is there a work around or fix? I miss being able to use my iPod on a daily/weekly basis when I feel the need to have most of my music library with me on the go. Thanks!

I've been reading on Mac Forums that music purchased from iTunes will not transfer to an iPOD Classic with Music. I have a Classic 160 GB with a lot of music purchased from iTunes over two decades. Can you confirm or refute this? I want to be sure before I plug this handy little device (which I also paid a lot of money for) which I use daily while I work far from internet and Wi-Fi into my MacBook Pro with the newly installed Catalina. Thanks.

I do have issues with the iPod shuffle 2G

Alright, I want to see the music that is on my iPod. I do NOT want to sync from my Mac to the iPod. I have old music on it that I really do not have anywhere else and I do not want to lose all that music I have collected since 2008. It is literally my auditory time capital. is there a way to do this?

I haven't upgraded to Catalina yet. I have a 5th gen touch and a 2nd gen touch, both of which I use constantly. Will these work with Catalina??

Great stuff! What year is the MacBook you used in this video?

My Mac will recognize the shuffle but I can’t seem to add music to it. Want to add some songs on it for my 8 year old but anytime I try to drag and drop a song it won’t take. I also made a playlist on Apple Music then clicked Autofill from Zoe’s playlist but then it says Songs cannot be added to the iPod because it already contains all the songs in the playlist “Zoe’s playlist”. But nothing has been added. Any suggestions?

Very nice video thank you I thought I would’ve needed to purchase an older Mac to sync to my 2nd generation iPod (2002)(uses fw400) but you’ve pointed me in the right direction going to order all cables and see if it works in 2024 I will update 😀

I’m impressed. You’d think after gutting iTunes it wouldn’t support them, but there you go. I was just playing with my original iPhone and almost nothing works. Messages, RU-vid, Maps, Weather, ITunes, App Store… none of them can connect to the internet over WiFi.

I have a first generation iPod shuffle. Was working perfectly until i loaned it to a friend. I had to reset to factory settings. Now I can't seem to sync it with Catalina. I'd like to select the songs that go on it. Can you assist or do a video? I have 2 classics as well, so this video was very helpful.

I just found a 2002 first-gen 10GB iPod for a few dollars at a G-sale, but don't have the charging cables. How do I charge it?

Regarding the Nano 5G video recording quality, it was 30 FPS 640x480 (SD), not HD so the quality is going to seem poor compared to even modern 720p HD which is the minimum standard for digital video recording these days. In 2009 when the Nana 5G was released that was not a awful spec for consumer video recording. By comparison, the iPhone 3GS which was the first iPhone to add video recording as a feature, only recorded in 640x360 (VGA, SD). The Flip Camera, a then popular consumer digital video camera (later bought by Cisco and then discontinued not long after), sold a lot of SD quality cams at the time. HD cams existed but where more expensive, needed more powerful computers to work with HD video files, and as a result where not standard just yet (Flip did sell one then though). It’s pretty easy to look back at video formats of the past and think “wow, that’s crappy” when it’s only us comparing it to modern Hd 4K HDR, etc. Formats like laserdisc and DVD looked pretty good compared the more dominant VHS standard at the time. Just as stereo records or tape sounded more “HiFi” then mono records or tape. And stereo movies will seem if they don’t already crappy compared to surround sound and Atmos and such.

How can ya download music to a old 2000 Ipod classic 1rst generation? It has the fire wire ports that I can't find a USB adapter for.

Impossible for me to download audiobooks from my Books library onto iPod shuffle in Catalina. (I listen to audio while swimming laps, so I need that content to load onto a waterproof shuffle.(

I just received an IPOD classic, but I am unable to sync my music to my iPod. In finder my IPOD is visible, I am using Catalina so no iTunes

Ok, time for an update: Does the first gen iPod sync with a Mac with an Apple M1 chip and Big Sur? My iPod Classic syncs with an Intel Mac and Big Sur, so I assume it would...

When I plug my iPod classic into my Macbook Pro, the iPod says "synchronizing." The music on my iPod is from another computer, which I no longer have. I don't want my iPod to be erased. I want all the music on my iPod to be put onto my MacBook. Do you know what I should do?

What if I want to sync manually? Music app doesn't allow to add/delete files.

okay, my iPod classic plugs in and is recognized in Catalina, but none of the music will play! is there something I'm doing wrong?

what about iPod nano 6th generation? I have yet to update to OS Catalina, as I still use my iPod nano for podcasts and music and have read that it won't sync.

Hi...my iPod classic does not show in finder. Any suggestions?

Hi! I recently updated my macbook pro to Catalina. Before the update I was able to listen to the music of my 2005 iPod after that iTunes doesn't want to play the music of my iPod. I can see the songs but when I press the play button nothing happens. What can I do? Thank you!

This did not work for me. I have an 6th gen Classic iPod. I see the device in Finder but the icon looks more like an disk drive than an iPod. All I see is a list of files. Maybe they stopped supporting it again in Catalina?

Hi. I have recently purchased iPod Photo 60GB. It works perfectly but does not sync with itunes on both Mac and Windows. I assume that there is some software issue with it since Windows asked me to format it when I plugged it for the first time as it was used with Mac before. Sadly I cant use it anymore. Could you please help me. Many thanks!

I recently got an unused (I think) ipod shuffle gen 2. It was not previously installed on older versions of my Mac OS. When I connected to Catalina 10.15.2 it shows up in Finder and in Music. I used autofill in the Music app and it now shows in Finder as the 1GB of storage almost filled. But neither Finder nor Music list any content. And when I try to listen I get a second of garbled music and then nothing except the on/off light flashing red. Any ideas on how to proceed?

I have an iPod classic 160gb, and I've had nothing but trouble getting Podcasts to sync. Music syncs just fine, but Podcast will not update. The podcasts that show in the finder are not the most recent. I've gone into the podcast settings to make sure that it only updates new podcast episodes, but the Finder continues to not show the most recent episodes. Not sure why Podcast app and the finder are not syncing properly.

I have an ipod Nano and now having trouble adding podcasts from the podcast app on my Mac. Podcasts no longer appear in the ITunes app on Mac and there's a separate app for podcasts. You say to choose sync on the Mac app but then it gives a message it will delete everything from the ipod and sync with the current list on the app.. I don't want everything deleted, just want to add podcasts.

Having trouble syncing with M1 MBA without iTunes! Any suggestions?

Thank you so much for your video,I still use my iPod shuffle for exercise and workouts,I realize it's old and out dated but who wants a clunky iPhone when the shuffle is so stinkin' lightweight and just perfect for workouts?? I was happy that it is possible to still sync with my shuffle from watching you...I am able to see my entire list of songs that were previously downloaded on my shuffle(in My Music-under these categories...artist, title, album, time or genre) but I cannot see all those songs in my 6 organized playlists with this new Catalina update. I just haven't figured that out yet. I want to continue to be able to add/delete songs on the playlists that I made for my shuffle...right now, like I said, in Music it's just one long list of all the songs on the shuffle. It's VERY frustrating because it used to be sooooooo EASY!!! And I can't seem to find a video to show me that yet....so I did experiment a little already, just not sure what the right way is and I don't want to push the wrong thing. I connected my iPod shuffle to my computer and I see it In Finder, as you mentioned. And at the top there are 4 tabs, General, Music, Podcasts, Audiobooks. I clicked on General and it says my iPod is up to date. I also see at the bottom the sync button. I clicked on it and nothing happened. Then back at the top, I clicked on the tab music, and i have the option to sync to my iPod shuffle, but when I click in the little box a new box pops up and says: Are you sure you want to remove existing music from this iPod and sync with this library? then it says: music synced to my iPod from other libraries will be removed and items will be synced from this library. In my Music library, there's a tab that says sync settings. I clicked on the tab, and that same box with the same information/directions from Finder appears again. In Finder or In Music, is this what I should click in order to get all my iPod shuffle songs/music synced and maybe able to see them organized into my 6 playlists, or do I have to start all over? Kinda scary when it says remove existing music, ya know? How can I recover or see the music by the playlists that I organized on the shuffle and not just one long list as it is now? I would certainly appreciate your thoughts or advice but I also understand if you don't want to waste your time on such an old gadget..I mean I still can listen to all of my playlists, which I can keep playing everyday for workouts but it's no fun when you can't manipulate or change the songs(add/delete) anymore when you want to.

My MacBook pro, using Catalina, will not copy songs to my iPod Classic. Tried everything you say in this vid, but it still won't cooperate. When I use Finder to look inside and check 'Manage Storage', it only shows the individual songs, not as albums or artists. It lets me delete songs, which is a pretty tedious procedure trying to find each individual song, but it won't let me put any files on to the device. Grrr.

I'm thinking about getting an iPod Classic, 7th generation maybe, will it still sync to my computer if it has Cortilina ?