As a teen growing up in the 90's, I was obsessed with two things: posters of boys and cars on my bedroom walls, and owning an Apple computer. I spent hours modifying my Windows 98 SE desktop to look "like a Mac", hunting down Mac OS 9 desktop wallpapers, system icons, and themes which made my Start Menu look like an Apple logo.

Hooverphonic (Renaissance Affair), Nick Drake (Pink Moon), and J Ralph (One Million Miles Away) played in Volkswagen television ads. The world wide web was in the middle of a paradigm shift, as the first wave of user-generated content hit Tripod, Angelfire, and Geocities. In an era before blogs, personal websites gave users a sense of credibility and legitimacy as digital designers and self-proclaimed hackers. Sites built with Macromedia Flash generated respect among teen audiences for their epileptic seizure-inducing animations and autoplay music. Right-click blocking javascript, which prevented visitors from viewing a site's source code, was considered cool.

Apple found itself caught up in the fashion of the moment, its aqua style buttons and striped design elements mirrored on hundreds of thousands of personal websites alongside colors inspired by its Blueberry, Grape, Tangerine, Lime, and Strawberry iMac G3 computers. At the turn of the century, the iPod became the ultimate public statement of peer-to-peer music file sharing, popularized by Napster, Limewire, and Kazaa. Instead of competing on hardware specs, Apple offered a unique aesthetic and user experience to young tech evolutionaries, and captured a dedicated following.

No one understood this better than late CEO Steve Jobs, who famously prioritized product development, and warned that product companies led by sales and marketing executives were digging their own graves. Today, Apple is led by sales and marketing executives.

1999   PowerMac G4, graphite (Mac OS X 10.2 Jaguar)
2004   iBook G4 12-inch laptop, white (Mac OS X 10.3 Panther)
2004   AirPort Express, gen 1
2004   iPod Photo, gen 1
2006   Macbook 13-inch laptop, white (Mac OS X 10.4 Tiger)
2006   iPod Nano, gen 1
2010   iPhone 4, white (iOS 4)
2010   iPod Touch, gen 4
2011   iPhone 4S, black (iOS 5)
2012   Macbook Pro Retina 13-inch laptop (Mac OS X 10.8 Mountain Lion)
2012   AirPort Express, gen 2
2013   iPhone 5S, space gray (iOS 7)
2014   iPad Mini 3, WiFi + Cellular, black
2015   Retina Macbook 12-inch laptop, gold (Mac OS X 10.11 El Capitan)
2016   Retina Macbook 12-inch laptop, space gray (MacOS 10.12 Sierra)
2016   iPhone 6S Plus, silver (iOS 9)
2017   Retina Macbook 12-inch laptop, space gray (MacOS 10.13 High Sierra)
2017   iPad Air 2, WiFi, black
2017   iPhone 7, black (iOS 10)

Above: A detailed list of product purchases from Apple, spanning almost two decades. Technically the PowerMac G4 was a gift from my Dad. Thanks Dad!

Apple's user experience has taken a back seat to unilateral and arbitrary decisions: useful ports have disappeared from laptops, fingerprint security was eliminated from their latest phone, dark patterns rule the mobile experience, MacOS and iOS suffer from an unending series of bugs and security vulnerabilities, the entire wireless router division was taken out back and shot years ago, and somehow prices are skyrocketing.

For years, Apple's prices were justified. Laptops built with an aluminum chassis, high quality components, an impenetrable unix-based operating system, excellent customer service and warranties. You got what you paid for, the products lasted forever, and so did their resale values. But $1,000 for an iPhone X? You've got to be kidding me. The lackluster iPhone 8, which sells for $700, still uses LCD screen technology and a proprietary lightning connector. Competitors like OnePlus offer a much more efficient AMOLED screen and USB-C charging - for $500.

Don't Confuse Security For Privacy

Starting with the iPhone 5S, Apple set the benchmark for mobile device security. Today's iOS devices offer a suite of security features, including a secure boot chain, secure enclave co-processor, AES 256-bit cryptography, and app code signing. Desktop products are similarly well equipped.

While hardware security will prevent a thief from digging through your personal or corporate secrets, it won't protect you from the No. 1 threat to your privacy: Apple. MacOS and iOS send an enormous amount of telemetry to Apple servers every minute, including during boot, bypassing user-based outbound firewall methods. Some MacOS services even send data over port 80, unencrypted!

Port Hidden App Outbound Connection   80 avconferenced   80 captiveagent   80 identityservicesd   80 itunes   80 systeminformation

Port Hidden App Outbound Connection  443 akd  443 appstore  443 appleidauthagent  443 apsd  443 ckkeyrolld  443 cloudd  443 geod.xpc  443 commerce  443 keyboardservicesd  443 mapspushd  443 nsurlsessiond  443 parsecd  443 passd  443 photolibraryd  443 softwareupdated  443 stocks.appex  443 storeassetd  443 systemmigrationd  443 touristd

Nefarious Laboratories also discovered Apple devices connect to every few seconds, relaying Safari and Spotlight search suggestions to Apple - even when users disable those features. They're essentially keyloggers. Apple devices also connect to for DNS requests, bypassing your local network settings. This means every domain you visit, e.g., is sent unencrypted over the internet to Apple.

Apple recently announced plans to hand control of Chinese customers' data to a state-run firm in China, raising further questions about how it handles private user data at home and abroad. With proposed legislation designed to open data to all levels of law enforcement, privacy advocates are especially concerned.

He's Dead, Jim

Do I regret living in Apple's ecosystem for almost two decades? Not at all. Apple once possessed an intangible magic which reflected their quirky, niche audience (artists, musicians, and software developers) who built their creative legacies by looking at the world sideways. But that magic is gone, leaving behind a rotten apple core. The company now spends its time chasing the Chinese market, building campuses fit for megalomaniacs, sacrificing privacy for convenience, and ignoring the pleas of its once loyal fan base. Die fetten jahre sind vorbei: The good times are over.

Published January 20, 2018

Update June 20, 2018

Quentin Carnicelli, founder of MacOS software development firm Rogue Amoeba, has publicly slammed the "sad state" of Apple's hardware lineup, which has been deteriorating for years.

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