Apple Dropped Plan for Encrypting iCloud Backups →

January 21, 2020 · 15:11

Joseph Menn, reporting for Reuters:

More than two years ago, Apple told the FBI that it planned to offer users end-to-end encryption when storing their phone data on iCloud, according to one current and three former FBI officials and one current and one former Apple employee.

Under that plan, primarily designed to thwart hackers, Apple would no longer have a key to unlock the encrypted data, meaning it would not be able to turn material over to authorities in a readable form even under court order.

In private talks with Apple soon after, representatives of the FBI’s cyber crime agents and its operational technology division objected to the plan, arguing it would deny them the most effective means for gaining evidence against iPhone-using suspects, the government sources said.

When Apple spoke privately to the FBI about its work on phone security the following year, the end-to-end encryption plan had been dropped, according to the six sources. Reuters could not determine why exactly Apple dropped the plan.

“Legal killed it, for reasons you can imagine,” another former Apple employee said he was told, without any specific mention of why the plan was dropped or if the FBI was a factor in the decision.

That person told Reuters the company did not want to risk being attacked by public officials for protecting criminals, sued for moving previously accessible data out of reach of government agencies or used as an excuse for new legislation against encryption.

If this is true, then Apple’s pro-privacy campaign is only true if you refrain from using iCloud. Unfortunately, iCloud Backup is the only automatic backup system supported by iOS, although you can go back to making local and secure iTunes backups instead. We of course have no real clue whether our particular backups were accessed or not, but I assume nobody is searching people’s data who stay away from legal trouble.

That said, Apple should definitely introduce end-to-end encryption for iCloud backups, or educate its users about the dangers of using iCloud Backup at the very least.

iCloud Drive Still Has Sync Issues in 2018

December 11, 2018 · 11:31

I still rely on Resilio Sync (formerly BitTorrent Sync) to sync my files between Macs, an iPad, and an iPhone. It works perfectly but I have been considering switching to iCloud Drive ever since I upgraded to the 2 TB storage option (please give me a cheaper 500 GB and 1 TB option Apple — I don’t need 2 TB at this point in time).

I was trying to transfer an edited photo from my iPad to my MacBook Pro a few minutes ago. I saved it to iCloud Drive and went to look for it on my Mac. Not there. I checked my iPhone and verified it was synced. So I restarted my Mac. Nope, nothing.

Want to know what triggered the sync process? I created a new folder in Finder.

Seriously, Apple?

iCloud Photo Library Image Count Problems

August 30, 2018 · 11:19

iCloud Photo Library has been stellar since I started using it shortly after it launched. I have suffered no data loss or corruption so far (I have other backups of course) and it’s been a joy to use. Once I upgraded both my Macs to macOS High Sierra, I finally flipped the switch on both my iPhone and iPad, turning on the new High Efficiency formats for both video and stills. Shortly after doing that, Photos for Mac and iOS started showing different counts of all the images in my library — they fluctuate every few days:

  • iMac (Download Originals to this Mac) — 33701 photos, 70 videos
  • MacBook Pro (Optimize Mac Storage) — 33701 photos, 70 videos
  • iPhone X (Optimize Storage) — 33703 photos, 70 videos
  • iPad Pro 10,5″ (Optimize Storage) — 33704 photos, 70 videos
  • — 33771 photos and videos (which I assume means 33701 photos and 70 videos)

This worries me. I still have 5 or 6 gigs of free space on my 200 GB plan so everything should work correctly. New content is added properly and syncing still functions as it should but what the hell are those additional photos on my iPhone and iPad?

I spoke with Apple Support and before they are willing to continue diagnosing the issue, they asked me to first log out and log back in to iCloud on every device. Since that would require at least 1-2 days of syncing (realistically 2-4), I’ll need to wait for a more opportune moment.

March 15, 2018 · 10:43

My iCloud Music Library is f*cked. Apple has been on it since yesterday and so far I’ve been on the phone for about four hours. Should get another call soon. The problem is that changes don’t sync between my devices and my HomePod is unable to play the music I purchased in the iTunes Store.

Apple’s Should Pull Out of China →

February 20, 2018 · 08:36

John Gruber, on Daring Fireball:

I wish that Apple would provide a definitive list of all types of data that goes through iCloud, showing what is end-to-end encrypted (iMessage and FaceTime?) and what is not. This whole situations reeks to high hell, but I don’t know what Apple could do other than pull out of the Chinese market entirely.

That’s exactly what they should do — pull out of China entirely. End-to-end encryption doesn’t guarantee complete security, since a lot can be obtained from analysing just the metadata.

Fixing Text Shortcuts Sync in iOS and macOS

September 27, 2017 · 07:15

One day, a few years ago, I got the runaround from Apple once again — my text shortcuts stopped syncing and they told me to wait for the next version of iOS. This was right after iOS 8.0 came out. Another year? No thanks. I found my own solution. I had to go through this again, after updating to iOS 10 last year. So that’s twice since the feature was added — not bad, not perfect.

Continue reading →

Jason Snell on the New iCloud Features →

September 21, 2016 · 11:16

Jason Snell:

Now, I may not be the perfect user for this feature, but I wanted to give it to try. And I definitely saw it in action, but I can’t call it a success. It was, in fact, the single most frustrating moment I spent with macOS Sierra.

Here’s what happened: I was editing a podcast in Apple’s Logic Pro X, and my project was stored on the Desktop. All of a sudden, the voice of one of my podcast panelists simply vanished from the mix. I quit and re-launched Logic, only to be told that the file in question was missing. Sure enough, a visit to Finder revealed that Sierra had “optimized” my storage and removed that file from my local drive. I’ll grant you, the file was a couple of weeks old, and very large as most audio files are. But I was also actively using it within a Logic project. Apparently that didn’t count for anything?

So that’s bad. That’s enough for me to turn off that feature and never use it again—or at the very least, never keep my project files on the Desktop or in the Documents folder.

To add insult to injury, at the time my files were deleted, my hard drive had approximately 80GB of free space. Why were the files deleted? I have no idea, but I suspect a bug in how Sierra was viewing the stock internal SSD of my iMac, because it’s also warned me that it didn’t have enough space to back up a 64GB iPhone with more than 100GB free, and gave me a “you’re about to run out of disk space” warning with 60GB free. So not only did Sierra remove files that I was using, it did so without any necessity.

At this point I downloaded all my files from iCloud, copied them to a file server just in case, and turned off both the Manage Storage feature and iCloud syncing of my Documents and Desktop folder. It’s a nice idea, but I’m not willing to have the place on my Mac where I keep key projects and documents to be a place I can’t count on. Think twice before enabling this feature.

I use BitTorrent Sync Pro to synchronise my Desktop and Downloads folders between my Macs. I can’t see myself moving away from this solution in the near future and switching to iCloud.

Apple to Hand iCloud Encryption Keys to Users →

March 18, 2016 · 19:12

Wayne Rash:

According to a number of press reports, Apple is in the process of revamping its iCloud storage service to increase security by divesting itself of the task of keeping users’ encryption keys.

Currently Apple keeps the keys to access iCloud accounts, which means, among other things, that Apple can provide information to authorities when presented with a warrant. The company provided such information from the iCloud account of Sayed Farook, the terrorist who killed 14 county employees late last year in in San Bernardino, Calif. Apparently that’s now about to change. If the reports are correct, Apple is planning to offload the storage of encryption keys so that users control their keys, and they’re accessible only through a password.

This way, even Apple cannot gain access to your encrypted data, no matter how much it may want to and no matter how many government subpoenas it receives. It can’t honor court orders to provide the data because the company has no way to decrypt it.

This is to be expected. I’d like to think that Apple would have gone down this route without the current FBI fiasco taking place, but perhaps the latest events have just accelerated their plans.