Category: non-technical

black and gray vinyl record player

How To Always Sync Your Purchased Music Between Devices Into Apple Music

  

If you’ve purchased music outside of Apple Music (for example, you’re a DJ and bought your music from Beatport, or maybe you’re supporting your favorite indie artist on Bandcamp) and want it to sync across all your devices, you might have noticed that Apple Music doesn’t always reliably upload your files to iCloud. Here’s the reliable method I’ve found that actually works.

The Problem

Simply dragging music files into Apple Music often results in them sitting locally on one device without ever syncing to the cloud. The app needs a specific nudge to recognize new files and begin the upload process.

The Solution

Follow these steps exactly, and your music will upload every time.

Step 1: Convert to AIFF

Before importing, convert your music files to AIFF format. While Apple Music supports various formats, AIFF consistently works best for cloud uploads. I don’t know why this is, I just know that anecdotally, this is where I’ve had the best luck.

If you have ffmpeg installed, you can convert files with this command (which will preserve any metadata and album art):

ffmpeg -i input.mp3 -write_id3v2 1 output.aiff

For batch conversion of multiple files in a folder:

for file in *.mp3; do ffmpeg -i "$file" -write_id3v2 1 "${file%.mp3}.aiff"; done

Step 2: Create a Fresh Temporary Playlist

Open Apple Music and create a brand new, completely empty playlist. This step is crucial and must be repeated each time you want to import new music. Don’t reuse an old playlist.

Step 3: Drag and Wait

Drag your AIFF files from Finder directly into your new temporary playlist. Once the files appear in the playlist, wait about 10 seconds. Don’t rush to the next step.

Step 4: Close and Reopen (The Critical Step)

Here’s the trick that makes everything work: completely quit Apple Music and reopen it. For whatever reason, Apple Music won’t analyze and upload your files until the app has been restarted. This seems to be what triggers the cloud sync process.

Step 5: Monitor the Upload

After reopening Apple Music, give it about a minute to begin processing. You can check the upload status in two places:

  • Bottom left corner: Look for upload progress indicators
  • Songs view: Open the Songs panel to see individual tracks as they’re being uploaded

Once the uploads complete, your music will be available across all your devices through iCloud Music Library.

Step 6: Move to Your Real Playlists

Now that your tracks have been uploaded to the cloud, you can add them to any of your regular cloud-enabled playlists. The temporary playlist served its purpose, and you’re free to organize your newly imported music however you like. These tracks will now sync properly across all your devices.

Why This Works

Apple Music’s cloud sync mechanism apparently doesn’t continuously scan for new files. The app restart forces it to re-index your library and discover the newly added tracks, triggering the upload process. Using the temporary playlist seems to tell Apple that these are external files that you would like to sync up to the cloud.

This workaround has proven reliable when the standard drag-and-drop method fails, ensuring your purchased music from other sources integrates seamlessly with your Apple Music library.

Stone wall

The XY Problem and how to avoid it

 

What is the XY Problem?

The XY Problem is asking about your attempted solution rather than your actual problem. This leads to enormous amounts of wasted time and energy, both on the part of people asking for help, and on the part of those providing help.

http://xyproblem.info/

Or to put it concisely, it’s when someone asks about their attempted solution, rather than about their problem.

I’m going to exaggerate to illustrate an example here, because I want to make it crystal clear what’s going on here.

Let’s say you work at a carving factory, and you’re in charge of all of the tools that the carvers need to do their job. When a tool breaks, a carver comes to you for a replacement. And let’s also say that each carver is tasked with taking a 10′ x 10′ x 10′ block of stone and reducing it down to a 1.5′ x 1.5′ x 1.5′ smooth cube.

A carver comes up to you and says “I need a new chisel, mine broke”. So you happily provide her a new chisel, satisfied that you’ve done your job and that she’s doing hers. Except, the next day, the same carver comes back and says “I need a new chisel, mine broke” again, so with a bit of a puzzled look on your face you go get her another chisel. The next day, same carver, same request again. And the day after. And the day after that.

You also notice that some carvers have completed two full 10′-cubed-to-1.5′-cube stones this week, while the one who has burned through 5 chisels has barely made any progress. The other carvers have been using diamond-tipped saws and jack hammers and other heavy duty tools in addition to the chisels, depending on how much material they were trying to remove at a particular time.

This is the XY Problem. The carver has spent so much time focusing on what she thought was the solution (“just keep getting a new chisel every time mine breaks”), instead of asking what the actual problem was (“how do I remove a lot of material in the most efficient way possible?”) and in doing so wasted her time and the company’s resources.

In a support-based industry like IT, this can be a depressingly common thing to deal with. Many times, the people you are tasked with supporting learned to do a particular task one way, and so just kept on doing that same task over and over without ever questioning why it was done that way, or if it was ever even necessary in the first place.

It’s completely understandable too – change is hard, and maybe they even got really efficient at doing that task that way, but that doesn’t mean there isn’t a better way to do it, or that it’s even necessary to do at all.

One of the most valuable skills I’ve learned is to pick up on when someone’s presenting me with an XY Problem; where they’ve started describing how they want me to solve a problem, rather than telling me what the end goal they’re trying to accomplish is and what they’ve tried in the process. I don’t call the person out because that does nothing but put the requestor in a defensive posture (completely unhelpful) and put me in a frustrated here-just-let-me-do-it state; I just try to get at the desired end state by probing and then re-framing their thinking in terms of what I would do if I were in their shoes. And by doing so, you align yourself with the other person making them much more likely to take your advice.

What is this place?

 

I am constantly both impressed with myself at how I solve complicated problems and disgusted at myself at how I manage to forget how I solved those same problems at some point in the future.

This blog will primarily be used as a more permanent home for the various solutions that I come up with as well as random thoughts I have about how best to utilize various cloud resources. Sometimes they may be specifically related to the industry I work in (airline / travel), and sometimes they may be more general.

If not a single person on the internet so much as visits this site, let alone finds its content interesting, that’s fine. I just wanted to put together a digital notebook that didn’t look like any of the other note-taking apps out there.