Trying to recover my old iTunes contents

Years and several computers ago, I won an iPod nano at work, and in order to make use of it, I burned a whole bunch of CDs on iTunes, over 3700 songs, which I then copied onto the nano and used it for several years. It’s been plugged in all this time, and it still works, so I was trying to figure ways to play the music through my windows PC, but from what I can find out, that seems quite difficult (correct me if I’m wrong, please).

So I thought I would try to get into my iTunes account and just play stuff directly through iTunes, and skip the nano. I recovered my account successfully, and I’m trying to install the current app from the Microsoft store, and I seem to be hitting a wall (or maybe I just need to exercise patience). I downloaded the installation app, but when I click to run it I get this little square box that says “Retrieving information from the Microsoft store…” and nothing seems to happen. Surely it’s not trying to download all those song files onto my PC, is it? And how long would that take? The storage on my iPod says that it fills about 11 gigabytes.

General or specific advice is welcome. I hope I am remembering correctly that I can play songs directly on my PC from those files.

This may or may not help you, but I’m just going to offer it up. A few years ago my iTunes became wonky, often only recognizing a subset of the songs I had bought or downloaded, sometimes not showing my library at all. I tried multiple times to update the software through Microsoft, and that did not fix it. At some point, however, I read online a recommendation that you not use the Microsoft store version, instead you find the executable version directly from Apple’s website.

That made no sense to me, but I was desperate, and I tried it and it worked. Since then, I have refused any updates, and it has worked fine.

As I said, something that may or may not work. Good luck, it’s a fragile ecosystem.

If the songs are still on the Nano and it’s just iTunes that isn’t working, try using the program CopyTrans instead to get the songs onto your computer. I’ve recommended that before, it’s a great simple little program that allows you to move songs onto or off of Apple devices.

I managed to get the program loaded and working (thanks, @Maserschmidt, I fiddled around with that, even though it just sent me back to the Microsoft store; apparently it works if you use the MS browser).

I guess I thought that all my songs were stored in the cloud somewhere (even though the events described in my OP were pre-Cloud, I think), but clearly not so. Apparently I have to load 11 gigs of songs from my iPod to the PC. So I will try @Eyebrows_0f_Doom’s suggestion of CopyTrans. I presume I will need some direct cable connection between the iPod and my PC, probably through USB, but I will have to investigate that further.

Thanks both for the help.

One thing I did was move all the file from where Apple and Microsoft put them to another folder, which I labelled in code. I haven’t had a problem losing songs since.

Losing songs? Is that a thing? I see where iTunes gets a lot of bad reviews, with an amalgamated score of 2.6 out of 5 stars. Is that one of the reasons? And thanks for the tip.

p.s. What does “labeled in code” mean? Just a name you made up, or a secret cipher, or something else?

My problem is that a lot of the things I copied from CDs back in the day are now getting flagged by iTunes as things I don’t have the right to play in this country, even though they’re my %#^@& CDs and of course I do. So they “disappear” them from my library.

I just labelled the folder “my music,” but as one word in a mix of languages with a spelling error, so that neither iTunes nor Windows discovers it (as they did once with a folder I’d labelled “fonts” in another language, which folder and files I STILL can’t find following a Windows update).

Of course, guilty without any chance of proving innocence. I’m sure it’s all there in the 90,000-page user agreement.

Sounds like you may have turned on iTunes Match, which essentially takes your ripped library of music and syncs it with the cloud so you can stream the music on any other device. It doesn’t actually copy any of your files, it just compiles a list of songs and then points to the cloud version on Apple’s servers instead. It’s more like an Apple Music streaming playlist that’s based on your original library. I can see how there could be rights issues there, because they’re not “your” songs. I never enabled iTunes Match, nor did I ever purchase any DRM’d music from the store, so I haven’t seen that problem. You might check into that.

As for the OP, for similar DRM-related reasons, music is not meant to be downloaded from an iPod, only uploaded to an iPod. However, I think you can just plug the iPod into the computer and then play the songs in iTunes. At least that was true back in the day, it may not be possible anymore.

No (just checked); nor do I have Apple Music. I think my specific problem is that I burned the CDs in the US and then moved to Canada, and Apple knows where I am: people aren’t supposed to stream music across a border. I now just have spotify pull from my library: they have their own problems, but none letting me play my own music.

Is the computer/hard drive onto which you ripped those 3,700 songs gone?

Yes, as I mentioned in the OP, it was several (probably 3) computers ago, and since I had the songs on the iPod, which I assumed at the time would be their ultimate destination, I felt no need to keep another copy.

As for general progress on my question, I went to Best Buy to see if they had a 30-pin to USB converter cable, but they didn’t. The nearest Apple store was too far away for convenience, so I ordered a non-Apple clone cable off of Amazon (risky, but it was only $6, probably less than the cost of driving around to look for one). The cable will be delivered tomorrow, probably late afternoon or early evening.

On the subject of just using the iPod as a Windows-compatible device from which to play the songs, rather than uploading onto my hard drive – various comments I have read online make me less than sanguine about the success of such a venture. However, I will try it and let folks know what happens.

That’s not the worst thing in the world, if you can accomplish it. That iPod isn’t going to last forever, and you really need your music files in more than one place.

Once you get the music to your Windows PC, you can use any one of a number of apps to play it. I’ve not tried it, but I’ve heard good things about MediaMonkey.

Did you rip these songs to mp3, m4a or some other format?

Update: the cable arrived today, and it seems to work, the iPod is recognized as a storage device. But my PC does not, at present, recognize any of the music files. From what I’m reading, it’s because they were ripped by iTunes into an Apple-only format. Copy/Trans can see them, but can’t play them on Windows 10. Apparently I need to load a Codec to translate the files into MP3 format. I loaded a Codec, but so far I haven’t figured out how to make it work. For one thing, I couldn’t find a way to specify a folder for the translated files to live, either in Copy/Trans or in the Codec settings. It’s going to take me a while to work all that out.

If any kind (and experienced) soul wants to hold my hand through this, which would really be above and beyond, maybe we could work through PMs or something.

Some are .mp3 and some .m4a; I don’t know what the difference is, or why—I assume ripped at different times on different machines.

What file format are they on the PC?

mp3 and mp4 are both unprotected formats, meaning no DRM, so there really isn’t any way for iTunes to determine they shouldn’t be playable, let alone what country you were in when you ripped them. Plus, just changing the name of the file or the folder as you’ve said you’ve done shouldn’t be able to make them playable in iTunes again. So whatever is going wrong for you, it’s something else.

Huh. Thank you: I was getting a specific error from iTunes about that, and I assumed it was because the files didn’t have whatever code they were looking for, but now it’s a mystery again. Anyway, the weird renaming thing seems to have worked.

They are not on the PC, they are only on the iPod. And I can’t see the file format using Copy/Paste (or anyway I don’t know how). But they were ripped on a PC, which I no longer have, using iTunes.