• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
TechApple

This is Apple Music’s worst nightmare – updated

By
Philip Elmer-DeWitt
Philip Elmer-DeWitt
Down Arrow Button Icon
By
Philip Elmer-DeWitt
Philip Elmer-DeWitt
Down Arrow Button Icon
July 23, 2015, 7:33 AM ET
Courtesy of Jim Dalrymple

The most remarkable thing about Jim Dalrymple—besides, you know, his facial hair—is his access to people in the know at Apple HQ. A simple “Yep” or “Nope” from the former news editor of Macworld is enough to make or break an Apple rumor. (See, for example, here.)

Jim Dalrymple is also a serious musician with a serious collection of digital music. You would think that if he ran into problems moving his library from iTunes to Apple Music, someone in Cupertino would see to it. [See UPDATE below.]

Dalrymple did run into problems. Not every problem I’ve read about on Apple’s support pages, but plenty. Mismatched songs. Duplicated songs. Songs from greatest hits albums excised from their original homes.

“I went through about 15 albums one night and manually added all of the missing songs,” Dalrymple wrote yesterday on in a 1,100-word post on The Loop that’s being widely recirculated today. “It was frustrating, to say the least, but I did it. I nearly lost my mind the next morning when I checked my iPhone and Apple Music and taken out all of the songs I added the night before. I was right back where I started…

“At some point, enough is enough. That time has come for me—Apple Music is just too much of a hassle to be bothered with. Nobody I’ve spoken at Apple or outside the company has any idea how to fix it, so the chances of a positive outcome seem slim to none.”

Nobody he’s spoken to at Apple? That’s not good.

This is worse:

“As if all of that wasn’t enough, Apple Music gave me one more kick in the head. Over the weekend, I turned off Apple Music and it took large chunks of my purchased music with it. Sadly, many of the songs were added from CDs years ago that I no longer have access to. Looking at my old iTunes Match library, before Apple Music, I’m missing about 4,700 songs. At this point, I just don’t care anymore, I just want Apple Music off my devices.”

“Apple music is a nightmare, and I’m done with it,” Dalrymple tweeted Wednesday to his 35,000 Twitter followers. Then he recorded a two-hour podcast with John Gruber for The Dalrymple Report.

I can’t wait to hear this.

UPDATE: Someone in Cupertino seems to have woken up to the fact that Dalrymple’s problem was a PR disaster for the new music service in which Apple has invested so much (starting with $3 billion for Beats). What followed the next day sounds like a high-level intervention. Dalrymple posted an update Friday afternoon that starts like this:

“It’s been an interesting and confusing day. I arrived at Apple this morning to talk to them about my issues with Apple Music and to hopefully fix my problems. The good news is that I have about 99 percent of my music back.”

That, as Merlin Mann might say, is nice for Dalrymple.

Meanwhile, the promised two-hour podcast with Daring Fireball‘s John Gruber in which Dalrymple’s missing music was discussed is not yet live. According to Dalrymple, it’s scheduled to air on Saturday with a disclaimer at the beginning that the problem has been fixed.

UPDATE 2: The podcast aired Saturday with an added intro by Dalrymple. The section about his Apple Music problem was edited out.

Follow Philip Elmer-DeWitt on Twitter at @philiped. Read his Apple (AAPL) coverage at fortune.com/ped or subscribe via his RSS feed.

About the Author
By Philip Elmer-DeWitt
See full bioRight Arrow Button Icon

Latest in Tech

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Tech

jason corso
Commentarydisruption
AI models are choking on junk data
By Jason CorsoMay 3, 2026
29 minutes ago
Sam Altman speaks into a microphone
AILabor
Sam Altman says the quiet part out loud, confirming some companies are ‘AI washing’ by blaming unrelated layoffs on the technology
By Sasha RogelbergMay 3, 2026
2 hours ago
Zoom is giving away $150K to ‘solopreneurs’ with no strings attached—as 33 million workers ditch corporate to become their own boss
SuccessCareers
Zoom is giving away $150K to ‘solopreneurs’ with no strings attached—as 33 million workers ditch corporate to become their own boss
By Orianna Rosa RoyleMay 3, 2026
7 hours ago
Disney’s new CEO is exploring a ‘super app’ for theme park tickets, movies and more
Big TechMedia
Disney’s new CEO is exploring a ‘super app’ for theme park tickets, movies and more
By Thomas Buckley, Lucas Shaw and BloombergMay 2, 2026
15 hours ago
Apple raises Mac Mini’s starting price to $799 after AI frenzy drains supply
AIChips
Apple raises Mac Mini’s starting price to $799 after AI frenzy drains supply
By Chris Welch, Mark Gurman and BloombergMay 2, 2026
16 hours ago
Unionized workers form alliance with rich tech giants on AI data centers, pushing back on local opposition and redrawing political lines
AIData centers
Unionized workers form alliance with rich tech giants on AI data centers, pushing back on local opposition and redrawing political lines
By Marc Levy and The Associated PressMay 2, 2026
16 hours ago

Most Popular

Scott Bessent on financial literacy: 'it drives me crazy' to see young men in blue-collar construction jobs playing the lottery
Personal Finance
Scott Bessent on financial literacy: 'it drives me crazy' to see young men in blue-collar construction jobs playing the lottery
By Fatima Hussein and The Associated PressMay 1, 2026
2 days ago
Gen Z is rebelling against the economy with ‘disillusionomics,’ tackling near 6-figure debt by turning life into a giant list of income streams
Economy
Gen Z is rebelling against the economy with ‘disillusionomics,’ tackling near 6-figure debt by turning life into a giant list of income streams
By Jacqueline MunisMay 2, 2026
23 hours ago
The American household just took an 81% margin cut. Wall Street hasn’t priced it in
Commentary
The American household just took an 81% margin cut. Wall Street hasn’t priced it in
By Katica RoyMay 2, 2026
1 day ago
Stop donating to Harvard and the Ivy League. There's a better option that MacKenzie Scott already figured out
Commentary
Stop donating to Harvard and the Ivy League. There's a better option that MacKenzie Scott already figured out
By Ed Smith-LewisMay 2, 2026
1 day ago
China dominates the world's lithium supply. The U.S. just found 328 years' worth in its own backyard
North America
China dominates the world's lithium supply. The U.S. just found 328 years' worth in its own backyard
By Jake AngeloApril 30, 2026
3 days ago
A Chick-fil-A worker got fired and then showed up behind the register to allegedly refund himself over $80,000 in mac and cheese
Law
A Chick-fil-A worker got fired and then showed up behind the register to allegedly refund himself over $80,000 in mac and cheese
By Catherina GioinoMay 1, 2026
2 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.