Getting your music off the old Mac

Get the files off the old Mac

Three ways, in the order I would try them.

Option A: Take the drive out and put it in a case (about $15 to $25)

This is what I would do. An enclosure is a plastic case with a USB cable that turns a bare laptop drive into an external drive. Unscrew the old drive, slide it in, plug it into your current computer, and it appears like a flash drive.

It is the most reliable route because the old machine's aging battery, power supply and logic board are all out of the picture. The drive is the only old part still involved.

One detail to get right before ordering. A 2004 Mac uses an older connector called IDE (also written PATA). Drives made after about 2006 use SATA. They look similar and they are not compatible.

Search for a 2.5 inch IDE USB enclosure. Buy a SATA one and the drive physically will not plug in. That is the most common wasted purchase in this whole job.

If opening a laptop is not something you want to do, any repair shop will pull the drive in a few minutes, and plenty will copy the files for you.

Option B: Turn the old Mac into an external drive (free, if you have the cables)

Hold the T key while the old Mac powers on. It acts as a plain external drive instead of starting up, and appears on another Mac's desktop. Safe, because nothing on it is actually running.

The catch is the cable. That era uses FireWire, which current Macs do not have. Bridging the gap usually takes two or three chained adapters, which cost more than the enclosure in Option A. Only worth it if you already own them.

Option C: Over your home network (free, and slow)

Share the folder and copy it across. It works, but that generation has slow networking and its file sharing does not get along with modern macOS. Expect a long transfer you have to babysit. Use this only if the other two are not possible.

What to copy once you can see the drive

The music. Look for:

Some versions call it iTunes Media, with a Music folder inside. Either way, that folder is the collection.

And this one file, which almost everyone skips:

It is the only record of your playlists, star ratings and play counts. The music files contain none of that. It is tiny, so copy it even if you are not sure you will use it.

One practical note. Copy the music folder specifically rather than dragging your whole old home folder across. Old user folders tend to hold documents you had forgotten were there.

Doing the copy: use tool 1 rather than dragging

You could just drag the folder across, and on a healthy drive that is fine. On a twenty year old drive the usual result is that the copy runs for two hours, hits one damaged file, stops dead, and leaves you unsure what made it across.

1 - Copy My Music.command does the same copy and handles that. It continues past files it cannot read, records which ones those were, and can be re-run to pick up where it stopped instead of starting over.

Double-click it. It asks for the folder on the old drive, then a folder on your computer to put it in. Drag each one in and press Return.

If it reports files it could not read, run it again. A second pass often gets files that failed the first time, since it only goes after what is missing. If the same handful fails every time, those files are damaged on the old drive, and it hands you the list.

Then unplug the old drive and put it away. Everything from here happens on the copy.

See what you actually have

A rescued library is almost never as big as it looks, and the reasons are specific and findable.

Double-click 2 - Check My Music.command and drag your music folder in. It reads every file once and writes a plain English report. A large collection takes a while, and it shows its progress so you can tell it is still working.

It only reads. It does not move, rename, convert or delete anything, so you can run it as often as you like.

When it finishes it opens a folder next to your music called <your folder>-report. The file to read is report.txt.

What the report is telling you

Five sections, in the order they appear.

1. What is in here

File types and how much of each. Mostly context, but a large pile of .wma files came from a Windows machine and some players will not play them.

2. Protected files (the important one)

This is the big one for a 2004 library, because there is no software fix for it.

Apple opened the iTunes Store in 2003, and everything bought from it until 2009 was sold with copy protection built in. Those files end in .m4p rather than the usual .m4a.

In practice they will only play in Apple's Music app, signed in to the Apple ID that bought them. Not a different Apple ID, not VLC, not Spotify, not a music server.

They are not broken and they are not corrupt. There is also no converter that fixes them, and any site claiming otherwise is either dead or not something you want to install. I am being blunt about that so you do not lose an evening looking for a tool that does not exist.

Your options, in order:

1. Sign in to that old Apple ID in the Music app. If you still have the account, the songs simply play again.
2. Re-download what you can. Some old purchases can be downloaded again in their modern unprotected form at no cost.
3. Leave them. If the count is twelve, this is not worth an evening. If it is four hundred, option 1 is worth chasing.

The report lists the affected songs so you can see them before deciding.

3. Files that are probably not real songs

When music lives in the cloud and was never downloaded, Apple often leaves a tiny file in its place. Right name, looks exactly like a song in Finder, contains no music.

The report flags anything too small to be real audio. On the collection I did recently, about a quarter of what looked like rescued songs turned out to be these.

Why it matters: it changes your real total. If the report says 6,000 songs and 900 are placeholders, you have 5,100. Better to know now than in a year.

What to do: try playing two or three of the flagged files. If they are silent or will not open, the rest are the same and they can go.

4. Identical copies

Files that are identical to each other, usually because the collection got copied between computers and both copies survived. Safe to reduce to one each, since the copies are the same object. Step 4 does this for you.

5. Files that could not be read

A handful means nothing. A large number clustered in one place can mean a failing drive, which is another reason to get everything off in one pass.

Clear out the spare copies

Once the report looks right, double-click 3 - Tidy My Music.command and drag in the same music folder.

This is the only tool that changes anything, so it is deliberately cautious. It sets aside two kinds of file and nothing else:

• spare copies of a song stored more than once identically, keeping one of each
• the placeholder files that are too small to contain music

It shows you the full list first, with how many songs you have now and how many you would be left with, and moves nothing until you type YES.

What it will not touch, on purpose: copy-protected songs, and anything that merely looks like a duplicate. That second one is the Step 5 problem below, and it is your call rather than a script's.

Nothing is ever deleted. Files move into a folder next to your music called <your folder> - Set aside <date>, keeping their original structure so you can see where each came from.

It also writes its own undo button. Inside that folder is Put It All Back.command. Double-click it and every file returns exactly where it was. You do not have to trust the tidy-up, because you can reverse it.

Leave the set-aside folder alone for a month or two. If nothing has gone missing, drag it to the Trash then.

The duplicates the report cannot find

This is where automatic tools do damage, so it is worth understanding.

The problem in one sentence: the same song can sit on your computer three times, in three files that do not look identical to a computer, even though they sound identical to you.

Along with the music, every file carries a little card of information: artist, album, year, artwork. Every time a library moves computers, or gets tidied, or has album art added, that card gets rewritten. The music inside does not change, but the file does. So anything comparing whole files sees two different things.

Catching those means comparing only the music and ignoring the card. It is usually the bigger share: on the collection I worked through, these plus the exact duplicates came to about 44% of the library, roughly 41 gigabytes out of 92.

And then there is the tier where duplicate-finder apps destroy things. Sometimes two files really are the same song and really are different audio:

• the live version and the studio version
• the radio edit and the full album version
• a 2010 remaster and the original CD
• a low quality rip and a high quality purchase

Only the last is genuinely a duplicate. You cannot tell these apart from the artist and title, which is exactly what those apps compare. That is how people delete a live recording they can never get back and do not notice for years.

So: when in doubt, keep both. A duplicate you kept costs a few megabytes. A recording you deleted is gone.

If this pile turns out to be big enough to be annoying, there are tools that compare the actual sound rather than the labels, and can tell a re-encoded copy from a different performance. Happy to point you at one if you get there.

If you use any other cleanup app

Tool 3 already follows these, so this is only for the moment you reach for something else. Most apps in this category follow none of them.

• It should move things, not delete them, somewhere you can reverse out of.
• It should show you the list first and wait for an answer.
• It should leave your original folder intact.
• The numbers should add up. Songs you started with equals songs kept plus copies set aside.

If an app cannot tell you where your files went and cannot put them back, close it.

Somewhere to actually play it

The simple answer is to point the Music app at your clean folder and be done.

The more durable answer is a small music server running on a computer at home, which indexes the folder and gives you a web player and a phone app for your own collection. Navidrome is the one I set up recently and it was straightforward.

Why I would bother: my aunt's and my parents' phones had started showing greyed out songs that would not play. The files were fine. A cloud music service had matched their songs to its own catalogue copies rather than storing theirs, and when those catalogue entries were pulled or restricted, their libraries quietly went dark in places.

The music was never gone. The pointers to it were. Owning the actual files is the only thing that fixes that permanently.