Marco Arment laments his perception that Apple’s software quality is in such a rapid decline that the company has “completely lost the functional high ground.” I like this turn of phrase, even if I don’t agree with the extremity of the sentiment. Marco expands:

“It just works” was never completely true, but I don’t think the list of qualifiers and asterisks has ever been longer. We now need to treat Apple’s OS and application releases with the same extreme skepticism and trepidation that conservative Windows IT departments employ.

I myself am particularly paranoid when it comes to Apple’s future. I spent the earliest years of my professional career working for the company, and to this day I consider the education I received at Apple to have been equal parts technical and philosophical. I learned not only how to build quality software, but why it should be done: to not only serve customers, but to delight and surprise them.

For years, my concerns about Apple’s future have been largely to do with my worry that those philosophical values are decreasingly shared by Apple’s engineering staff and management. And yet, over the years, I have been surprised and delighted by the steady stream of new, quality products that Apple releases.

The current state of Apple’s software does not particularly concern me. Are there embarrassing blemishes? Yes. Does the annual schedule for major OS updates seem rushed? Of course. Are there Apple employees in positions of power who do not share Marco’s and my enthusiasm for software that “just works?” I regret to surmise that, indeed, there are.

But I’ve indulged these doubts about Apple since shortly after I was hired … in 1996. The mysterious, seemingly magical nostalgic components of Apple’s past success have always seemed threatened by the rapid waves of change that undo and reconfigure the company’s priorities. After the NeXT acquisition in late 1996, many of my colleagues and I feared the influx of new engineers would spell the end of the Mac as we knew it. In fact it did, but the new priorities of Mac OS X meshed well with the old priorities of Mac OS 9, yielding what I believe is an undisputably better, more Apple-like operating system than Apple was likely to have come up with on its own. There were many fits and starts along the way, including questions about arcane matters such as filename extensions and case sensitivity. These were but a few of many questions that would seem to make or break the legacy of the Mac. Choices were made, hearts were broken, and the Mac lives on.

Since I left Apple in 2002, I have been no stranger to criticizing the company for its flaws. The mistakes they ship in hardware and software are sometimes so glaringly obvious, it’s impossible to imagine how any engineer, manager, or executive could suffer the embarrassments. And yet, sometimes these defects linger for years before being properly addressed.

The problem has also been a focus of popular geek culture at many, many times in history. Way back in 2005, Dan Wood of Karelia was so frustrated by persistent flakiness in Apple’s software that he encouraged developers to report an Apple bug on Fridays. It worked: myself, Brent Simmons, Wolf Rentzsch, Sven-S. Porst, and countless others were moved to file bugs not just that Friday, but for many weeks to follow.

Over the years I have never been at a loss for identifying problems big and small with Apple’s products, or with the way it conducts its business. I’m sure I had plenty of complaints starting in 2002, but I didn’t start blogging in earnest until 2005. Here are some highlights to remind you that things have never been fine with Apple:

2005 – Keychain Inaccessibility. I lamented the poor behavior of Apple’s Keychain Access app, even after improvements that came in Mac OS X 10.4.3. Nearly ten years later, to the delight of the folks who make 1Password, this embarrassment remains largely uncorrected.

2006 – We Need a Hero. I shined a light on the difficulty of implementing AppleScript support in applications. Things have steadily improved, but are still very frustrating and error-prone. At least now we have two automation languages to pull our hair out over.

2006 – All Work and No Play… Apple’s first Intel portable computer was a sight for sore eyes, but a cause of sore ears. The maddening “CPU whine” persisted through several iterations of the hardware design until the machines finally became more or less (to my ears) quiet.

2007 – Leopard Isn’t the Problem. Speaking of annual software release schedules, here’s my nearly 8-year old reaction to Apple’s failure to meet the planned release schedules for both Mac and iOS in parallel. Is Apple suddenly more fixated on marketing than on engineering? Not by my assessment that their statement way back then was “bluntly crafted, sleazy marketing bullshit.”

2008 – NSURLConnection Crashing Epidemic. Wouldn’t it be embarrassing if Apple shipped a bug so pervasive that it could crash any app that uses Cocoa’s standard URL loading mechanism? That’s what they did in Mac OS X 10.4.11, and it took them months to fix it. When they finally did, I ended up receiving a security update credit!

2009 – Is Apple Evil? Speaking of embarrassments, how pathetic is it that nearly 7 years after the iOS App Store debuted, capricious rejections are still a mainstay of iOS tech journalism? In 2009, I reacted: “Alongside the stubbornly perfected refinement of its products, marketing, and public image, the company has always worn blemishes such as these.” Some things truly never change.

2010 – Surviving Success. From the midst of “antennagate,” in which Steve Jobs accidentally coined the famous anti-advice “you’re holding it wrong.” I fretted that Apple was losing its marketing cool, and that Jobs should chill out:

He spins the truth in that barely plausible manner that used to be celebrated as the “reality distortion field,” but now comes off as purposefully dishonest and manipulative. We don’t have Jobs to blame any longer for Apple’s less tasteful distortions of reality.

2011 – Huh. I couldn’t find any particularly cogent complaints in my archives. Maybe I was too busy reacting with panic to Apple’s new Mac Application Sandbox. I did complain in an interview with The Mac Observer about “having to come to terms with the vast amount of stuff that Apple’s doing,” but that “it’s been a persistent, joyous complaint … that Apple is doing too much.”

2012 – Fix the Sandbox. Having fully digested the impact of the Sandbox on shipping apps, I drew attention to the many problems I saw in Apple’s approach to (allegedly) enhancing user security:

Given the current limitations of sandboxing, a significant number of developers will not adopt the technology, so its usefulness to users and to the security of the platform will be diminished.

2013 – Respect the Crowd. Oh, right, Maps. Remember when Apple used to have reliable driving directions, place data, and even public transit directions?

It’s all about the data. It doesn’t matter how beautiful Apple’s maps are, or how quickly they load, if they consistently assign wrong names and locations to the businesses and landmarks that customers search for on a daily basis. Apple has made significant improvements to their mapping data, and there are rumors, based largely in their acquisition of transit-oriented companies, that they may restore transit directions at some point. But to this day, Google Maps remains my go-to app for transit directions, while Google’s other directions app, Waze, gets my business for driving directions.

2014 – Breach of Trust. We’re getting so close to modern times by now that Apple’s tactless imposition of a U2 album on everybody’s iPhone, whether they wanted it or not, could be considered part of Marco’s current diagnosis of what ails Apple. The nut of my take on the incident:

It doesn’t matter much that Apple inserts an unwanted music album into your purchased list. But even a little move in a direction that threatens the primacy of users is a relatively big move for companies like Twitter or Apple, whose track records have inspired us to trust that we retain more authority over the personalization of these products than perhaps we do.

And now it’s 2015, and in the immortal words of Kurt Cobain: “Hey! Wait! I’ve got a new complaint.” Don’t we all. A company like Apple, moving at a breakneck speed, will undoubtedly continue to give us plenty to obsess about, both positively and negatively. I’ve been following the company closely since my hiring in 1996. Since that time, the company has consistently produced nothing short of the best hardware and software in the world, consistently marred by nothing short of the most infuriating, most embarrassing, most “worrisome for the company’s future” defects.

Apple is clearly doomed. I think Apple is going to be okay.