iCloud problems: my email to Tim Cook

Dear Mr. Cook,
Greetings. I am a long-time Mac user (since the early 90’s) and have been with iCloud since the early days when it was .mac (and I still use my .mac email address).
After many issues with iCloud, I have grown very disappointed and frustrated with the service, for which me and my wife each pay every month. Here are some of the problems I’ve found and have also been reported by many others:
  • The Photos app will initially show only empty thumbnail placeholders on my iOS devices and my MacBook Pro when iCloud is turned off then back on. Rather than download the thumbnails automatically, I have to painstakingly scroll through every thumbnail (I have over 18,000 photos) on every device in order to have them displayed. Without the thumbnails, it’s pretty useless as a photo library.
  • I’ve been on .mac/iCloud email since 2002. Two months ago, I just happened to notice that all of my iCloud emails were gone from iCloud. I could even date, based on my backups, when the even occurred, and I was on a plane that day (and as you could imagine, it’s not easy to accidentally delete over 17,000 emails manually). I contacted Apple support, and they were not helpful; after the call got lost by the first support person, I contacted a second who had no idea how to reinstall the backup I had and kept accusing me of manually deleting thousands of emails. It was clearly a server issue, and after researching it online myself, I was able to restore all but a few weeks of emails from a Time Machine backup. But this was clearly not good. I never even got a survey about the support team, which is odd since every interaction I’ve ever had with Apple support led to at least one email asking how they did. That suggests to me that the reps involved knew they blew it.
  • And today, for reasons I suspect are within the iCloud backend, I was locked out of my iCloud account and had to reset my password. Ever since, I have been plagued with frequent requests to log back into iCloud on all my devices, which as you can understand is pretty painful during the work day.
I still love my Apple devices, but admittedly have had to switch to alternative software at times (Airmail rather than Mail, Fantastical rather than Calendar and Reminders) because it’s become apparent even to a die-hard Apple supporter like me that Apple’s software has become less reliable and lacks many useful features. And this extends to paid services like iCloud. I do not understand why iCloud has such poor reliability of late, despite the status page always showing green, as if there are no problems. The iCloud issues today occupied a good deal of time, and I’m still dealing with persistent requests to log in. I wanted you to know, as that is perhaps the only way to help make things better. I’m not the only person with lackluster iCloud performance and reliability; my experience probably has been even better than what I’ve seen reported by others. But it is disturbing nonetheless. I would be happy to follow up with you or a delegate about this. Thank you for your attention to this matter.


Best regards,

David Toub, MD, MBA 

Sent with Airmail