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In hindsight, the trouble began in 2012. That’s when Apple moved OS X to the same yearly release cycle as iOS. Since OS X has always been the Peter that Apple robbed to pay Paul (the iOS release cycle), I was concerned Apple would be writing checks it couldn’t cash.

Later that year, iOS 6 was released with the whole Maps debacle. That fiasco, however, was easy to write off because Maps was so new, and any new mapping service was going to pale in comparison to Google. Given strained relations between Apple and Google, Apple had no choice but to divorce itself from Google Maps, as painful as that was for users.

2013 wasn’t any better for Apple. iOS 7 had massive battery drain and Wi-Fi connection issues, and Mavericks, released a month later, had some well-documented issues with Gmail.

So far 2014 is like the Keith McCready line in Color of Money: “It’s like a nightmare, isn’t it? It just keeps getting worse and worse.” It started with a September 9th livestream that barely worked, and when it did, gave viewers a chance to brush up on their Chinese.

iOS 8 problems

Apple launched iOS 8 on September 17 and for about an hour HealthKit-enabled apps could be downloaded. Then due to last-minute bugs in HealthKit, they were pulled. A week later, Apple released iOS 8.0.1, but, again, pulled it within an hour. While it did fix the HealthKit bugs, it introduced minor bugs like killing cellular connectivity and TouchID. Lastly, there are also reports of an issue where resetting your iOS device also deletes your iCloud Drive data. For the record, I recently reset my iPhone 6 Plus, and did not lose any data.

All of these show systemic failure in Apple’s beta testing. It’s inexcusable for a major new feature like HealthKit to be pulled right after launch due to missed bugs. It’s even worse when an update makes your phone unable to make calls. Clearly, Apple needs a little help in regression testing.

Even though Apple claims HealthKit is working, there are still issues. All week I’ve been tracking my steps and viewing the dashboard in Health.app. Today, it lost all the data and my dashboard was empty. If I try and view the data points, I just get a spinning wheel. It took three reboots and a ritual sacrifice to get the data back. It is very hard to have any faith in an app that arbitrarily loses its data.

iCloud Drive

Also part of iOS 8, but deserving of special mention, is iCloud Drive. iCloud Drive finally frees documents from an app’s sandbox and uses a Document Picker, where an app can open any compatible file from a folder in iCloud Drive. As an aside, the app will need to updated with the new document picker. While iCloud Drive for OS X is waiting for OS X Yosemite’s release, it was released for iOS 8 and Windows.

The problem I’m having is that it only sort of works. The biggest problem is folders. My iWork folders and documents sync between iOS devices, non-Apple application folders are a problem. For example, my GoodReader iCloud Drive folder only shows up when I open GoodReader on an iOS; it’s not on the web page, my Yosemite GM install, or my Windows 7 machine.

As a test, I created a folder named PDFs on the web. It’s not syncing to iCloud drive on either desktop OS. I tried uploading a file to the folder to see if that would force a sync, but it didn’t. Files put in the Apple-created Preview folder seem to sync fine. Clearly, something is weird with folder syncing. I haven’t been this worried about my data in iCloud since 2011.

I admit that running a beta release of OS X could yield problems. That said, since the version I’m running is allegedly the version the general public will be downloading soon, I’d hope it would all work. Also, I’ve always considered the iCloud.com website as the canonical truth for my iCloud data. The GoodReader folder not showing up there is disturbing. I reached out to GoodReader to see if they had any guidance and it seems like the issue is sporadic. Some user see the folder; some don’t.

So, what can Apple do?

Apple is famous for saying that there are “a thousand no’s for every yes”. Ironically, at the start at the video Apple asks: if everyone is busy making everything, how can we perfect anything?

This is a question Apple needs to ask itself. Also, it needs to ask “Is tying a major iOS update to new iPhone’s a good strategy?” I agree with Daring Fireball’s John Gruber and don’t think this is possible. At this point, Apple has gotten into the cycle of new iPhones and iOS in September, and new iPads and OS X release in October.

The problem is, Apple’s bad September could become a bad October, and a bad start to 2015. Next month we will likely see new iPads and Yosemite. iCloud drive will be usable by all devices. Next year, we have the Apple Watch. Each of these will need a dot update to iOS.

WWDC is a great place to introduce the new OSs. Maybe, though, a longer beta cycle and moving WWDC up to late April would help. Maybe, it’s time for Apple to accept that not everything they want to release can be tested accurately in three months. iOS 8 is a big, welcome, update, but maybe in this case, less would have more.

I will say that given Apple’s quality issues this month, I will be staying far, far away from the Apple Watch at launch.