iCloud Gets a Security Upgrade

Today Apple announced some nice updates to the iCloud security features. The following features now have end-to-end encryption on iCloud:

  • Device Backups
  • Messages Backups
  • iCloud Drive
  • Notes
  • Photos
  • Reminders
  • Safari Bookmarks
  • Siri Shortcuts
  • Voice Memos
  • Wallet Passes

End-to-end encryption means your data can’t be viewed on the server in these categories (if you opt in). Put simply, Apple will no longer be able to see the above categories of data. If Apple gets hacked in the future, the bad guys can’t see your data either.

Apple has very publicly stated an interest in protecting user privacy. I believe them. What is impressive about this is how they’ve added the encryption at Apple’s user-base scale. That can’t be easy.

At this point, it’s opt-in. You must go into the iCloud settings and click on Advance Data Protection. I will be opting in. Advanced Data Protection is in the latest iOS 16.2 beta. It will be available to all U.S. customers by the end of the year and rolling out to the world in early 2023.

One note of caution, however, is that this means if you ever lose passwords, the data is gone. Apple can’t help you. So get your password security sorted out before you push the button.

Craig Federighi did an interview with Joanna Stern on these updates. She did a great job explaining end-to-end encryption in the process.

Dropbox vs. iCloud

Now that Apple can share files and folders, I’m sorely tempted to let my Dropbox subscription expire. I’m generally not a fan of apps that embed themselves in the underlying operating system the way that Dropbox does on the Mac. Indeed on my laptop, I didn’t install the Dropbox hacks. When I need to upload a file there, I trigger a Keyboard Maestro script that gets me to the Dropbox website, and I drag and drop into the browser. Also, I don’t want to give another pile of money to Dropbox.

A few reasons are holding me back at the moment:

  1. iCloud Doubt Dropbox has always been rock-solid and fast. I’m not aware of ever losing a file through the Dropbox cloud sync, and I’ve always been impressed with Dropbox’s synchronization speed. Is iCloud up to that? It has been stable for me in terms of file and sync integrity. It’s definitely slower than Dropbox.

  2. Non-Apple People In the day job, I often have people I share files with that don’t own any hardware with a fruit logo. Historically, iCloud sharing has not been useful outside the Apple ecosystem. That is getting better now, but is it good enough yet?.

Apple could make this decision a lot easier for me later this month if they add additional features for iCloud sharing at WWDC. While I’ve got some time left on my annual Dropbox subscription, I’m keeping it as a backup, but I’m also trying not to use it. If I can get by a few months without having to resort to Dropbox, I’m probably good. Ideally, one cloud storage service is enough for me.

The Missing iCloud Storage Bump

In my post yesterday following Apple’s education event, I mentioned that I felt the increase of free iCloud storage for students from 5GB to 200GB was a good idea, and I hoped Apple would be giving us all more storage at WWDC.

Dan Moren feels the same, but more passionately. I think the single best reason for giving us increased storage is Apple Photos. They’ve built a platform that lets us take, save, and share photos, but it requires nearly all of us to make regular monthly payments so we have enough storage. This is annoying. Our Apple devices are expensive, and Apple is hardly cash-strapped. Moreover, a lot of people (perhaps most people?) refuse to pay for extra storage. I hear from readers and listeners all the time that have a problem with it. I expect the refusal to pay is even more common with non-geeks. They don’t pay. Their photos don’t get backed up.

So let’s take the capitalist approach. Taken to its logical conclusion, paltry free storage results in people losing their photos and being understandably pissed at Apple. Google is well aware of this because nearly every advertisement I’ve seen from them that has any relation to photos always points out they have free storage. These disgruntled consumers see that and move platforms.

I’m not even arguing Apple needs to make it free across the board. Just raise the free tier to something rational. 200GB seems about right.

iCloud Text Replacement

There has been a lot of press the last few weeks over iCloud’s lackluster text replacement feature. Brian Stucki wrote an excellent post documenting just how bad the service is.

I have to admit that I forgot iCloud even provided text replacement services. For years I would eagerly test out iCloud text replacement when there was a new version of iOS, but after a while I gave up. I could never get it to work reliably. Indeed, I wasted so much time trying to get it to work that I ultimately gave up and stopped trying.

I left my old job a few years ago, and iCloud text replacement still tries to occasionally drop in that old phone number even though I’ve fixed that entry repeatedly.

I think that is one of the challenges of iCloud. It covers so many different services that it’s easy to lose one or two in the mix, especially when it’s one that doesn’t work reliably. That has certainly been the case with the text replacement feature.

The good news is that Apple is now moving text replacement onto the CloudKit API, which is much more reliable and should, hopefully, solve the problem once and for all. Indeed, Apple representatives told John Gruber that this rollout would happen “in the next month or so“. I sure hope so.

iCloud Authentication Video

Apple has recently announced that starting June 15, any Mac app needing access to iCloud data is going to need an app-specific password. While this is a bit of a pain, it provides a significant increase in your security and I’m all for it. The gang at Fantastical asked me to make a video explaining exactly how to make an iCloud app-specific password. This video is for Fantastical, which is my calendaring weapon of choice, but you’ll be going through the same steps with any third party app starting June 15.

New iCloud Storage Pricing

At last week’s event, Apple announced new pricing for iCloud storage. You can now get a Terabyte for $9.99/month, which matches Dropbox. They have a lower tier at 200GB for $2.99 and 50GB for $0.99. There still is no method for family sharing, which means I’m currently paying for three people. I like that the pricing is now more in line with Dropbox and other cloud storage providers. I still think the 5GB free storage is not enough when we’re buying expensive iPads and iPhones. You can see the international pricing here.

“Organizational Issues”

MacRumors reports on an article about iCloud suffering from  “Deep Organizational Issues”. I’ve had my own set of problems with iCloud as of late but based on everything I’ve experienced with Apple, including just a tiny bit of the inside, I don’t think the iCloud stumbles have been a result of untamed bureaucracy or anything organizational. Everyone I’ve ever dealt with from Apple is incredibly focussed.

If I had to bet a nickel, I’d say the problem is that cloud stuff between multiple platforms (even platforms you own) is really, really hard. Dropbox and Twitter started small and got big slowly and they had plenty of growing pains along the way. When Apple releases a new cloud service, it immediately has millions of users. Apple still needs to prove they can deliver the goods in the cloud, but I have a hard time believing their cloud-challenges are organizational issues. 


iCloud Drive Syncing Improvements

A few weeks ago I wrote about my problems getting documents to sync with iCloud Drive. In response, I heard from several developer friends telling me that things were about to get better and to install the 8.1.1 developer preview. So I did. After using it for a week, and the beta going out to the wild yesterday, I’m pleased to report iCloud Drive document syncing is loads better with the latest updates. This morning I spent 30 minutes moving between my iPad and Mac on a large numbers spreadsheet and both devices were keeping up. In short, iCloud document syncing is manageable again. Third party apps, like Drafts and Mindnode, are also seeing the benefits of this update. If you’ve been waiting, or had a bad prior experience, update your Mac and iOS devices with yesterday’s updates and give it a try for yourself.

The reason I’ve been so critical of iCloud lately is because I haven’t dismissed it. I see real potential to using Apple’s cloud solution. I like its tight integration with the operating system and since I’m using all Apple hardware, it just makes sense for me. I’m also considering going deeper into tagging and assuming that Apple tags will be better supported with an Apple cloud. I hope the problems of last month are initial stumbles. For now, I’m just happy to see the service working again as expected.

iCloud Drive Stumbles

Over the past few weeks I’ve had a post it in development concerning iCloud Drive and document syncing. Through the beta process for both Yosemite and iOS, I had varying degrees of success with synchronizing documents through the iCloud drive, by which I mean it rarely worked. 

Apple made a lot of changes under the hood with these most recent releases and I understood that this was going to be difficult for awhile and I was going to face the host of evils that come with running beta software. However, I also expected that when these products shipped, everything would be sorted out.

I am under no illusions that Apple can magically become the masters of cloud sync overnight, especially when they’ve been behind competitors like Google for so long. I was prepared for a few rough patches as the software released but I was not prepared for the problems I faced when Yosemite finally hit the streets and iCloud Drive was a real thing and no longer a beta thing.

Originally, my ability to sync through iCloud Drive was crippled. My iPhone, iPad, and Mac all had different versions of documents on them despite numerous attempts to reset the system, including logging out of iCloud entirely, switching my .Mac identity to an “iCloud” identity, and even nuking my iPad entirely and starting again from scratch were all fruitless. The most frustrating part is that these failures were not only with third parties using iCloud drive, they were happening with Pages, Numbers, and Keynote as well. How are people at Apple not seeing these problems with their own apps?

For a few weeks, it just didn’t work for me. Sometimes I could get one device to sync with the other temporarily but then a few hours later it would stop. I spent way too much time trying to troubleshoot it and ultimately concluded the problem was probably something server-based or software-based and entirely out of my control. I was like a tribesmen trying to forestall a solar eclipse by looking at chicken bones. I knew at some level that all of my attempts to sort things out was pointless yet I couldn’t stop myself because I needed these documents to synchronize for my work. That whole thing I’ve always felt about my Apple products just working for me and letting me get on with my work went out the window and it drove me nuts.

The version of this post that I wrote a week ago, was a lot less generous than the one I am now posting. The reason for that is about a week ago things started to sort out for the iWork apps. At first, things would start syncing but just take a long time to do so. I’ve got a 20 MB numbers file. It took about 10 minutes to synchronize between my iPad and my Mac. They didn’t allow for simultaneous work but at least I knew I had the data available to me when I needed it. Since then the speed has increased even more. We’ve had a few updates to the iWork apps that have significantly improved iCloud synchronizing speeds as well. It still takes longer than it should to synchronize documents and I expect this is largely server-based. Also, it still is not perfect. I updated a Numbers spreadsheet last night on my Mac and then started working on it this morning on my iPad but realized, about 5 minutes in, that I didn’t have the changes synced from the Mac so I now had two inconsistent versions of the same document. Ugh.

On third party apps, things are still a mess. There was apparently a problem with 8.1 that makes iCloud Drive document sync cause apps using the service to hang up and, generally, break. Several of my favorite third party apps that use iCloud Drive are practically unusable at this point. I’m told the impending 8.1.1 update fixes this but I have to wonder how it got this far. 

I don’t know what to think about Apple and the cloud at this point. I think this is really important to Apple’s success (and my ability to get the most out of their products). Nevertheless, they keep stumbling. I know what they are doing at this massive scale is hard. However, Apple’s secretive nature combined with these obvious problems makes it appear they just don’t care, which I don’t think is true but nonetheless frustrating when it interrupts my flow. I suspect the truth is that the iCloud team is pedaling like mad and don’t want to publicly acknowledge these problems but instead just fix them. I sure hope they do. I’ll be reporting back on iCloud Drive and hope things get better. For now, you can hold on to your Dropbox account.

Can Apple Deliver on the Promised New iCloud Services?

Now that WWDC is over and we’ve all had a chance to digest Apple’s announcements, I’ve been thinking about Apple and the cloud. Right up until WWDC, there were several questions in my mind.

1. Does Apple realize how important cloud data is to the future of iOS and the Mac?

This question seems silly in hindsight but right up until a few weeks ago, I wasn’t even sure this was on their radar. It seemed as if every few years Apple announced some new semi-cloudy initiative but things never really changed. It felt as if this were an issue that received lip service but no actual attention. That changed this year with Apple not only announcing some very aggressive cloud tools but also committing to use these very cloud tools for their own software tools (including picture management).

2. Is Apple working on catching up with cloud services?

I use the term “catching up” intentionally. While there are many areas for which Apple remains an industry leader, providing fast, reliable cloud services is not one of them. Moreover, because they are so secretive, we had no idea whether they were taking steps to improve the situation or sitting around convincing each other this isn’t a big deal. (See point one above.) 2014 WWDC’s announcements including iCloud Drive, CloudKit, and the initiative to store all of our photo libraries on their servers answers this question. They have been working on it and they’ve got some pretty big aspirations, which leads to the last question.

3. Can Apple deliver worry-free cloud services?

All of the promise of WWDC will be forgotten if these new services are slow, unreliable, or otherwise not up to snuff. This is the part we are waiting on. While the narrative that Apple can’t do the cloud is fun enough, it’s not really true. They serve a lot of data every day through their app stores. Pieces of iCloud, like contact and calendar sync, have always reliably worked and they include millions of users. Apple’s cloud problem, in my mind at least, has always involved pushing big blocks of data. Does anybody remember how bad iDrive was at moving anything bigger than a Pages file?  

In fairness, this question will not get a definitive answer on day one when all of this goes live. You can’t reliably load test these types of services for hundreds of millions of users. You do your best, stock up on duct tape, and then you push the green button and stand by. I’m certain there will be some hiccups. However, at some point in the not too distant future, we all will make a decision whether services like iCloud Drive are just as reliable as Dropbox or not. Only in that final judgment will we be able to answer this last question.