For a company that values simplicity, particularly when it comes to product branding, Apple (NASDAQ:AAPL) continues to dig deeper into a well of overly complicated iPhone names. Just ask former Apple ad man Ken Segall, who came up with the original iMac's name, a brand that has stuck around for over two decades and still exemplifies the all-in-one computer form factor. Segall argued last year that 2017 was an opportunity to reset, hoping that Apple would streamline iPhone names and ditch the "S" once and for all. Instead, Apple went with iPhone 8 and iPhone X.

You can probably guess how Segall feels about iPhone XS Max.

Gold iPhone XS and XS Max next to each other

iPhone XS and XS Max. Image source: Apple.

Dreading new iPhone names

In a new blog post, Segall says he feels "a sense of dread" every September when he wonders what Apple is going to name its latest and greatest handsets. The Mac maker is now waging "a war against common sense," in Segall's view, as iPhone names are becoming increasingly -- and needlessly -- complex over time. Here's how Segall felt about the 2017 lineup:

Last year's models set new standards for complexity. We had an 8, 8 Plus, X and SE. That's two numbers, one Roman numeral, one paring of letters, plus an odd numerical gap between 8 and 10. Or, in Apple lingo, between 8 and X.

On the bright side, Apple has unified the 2018 lineup under the common identifier of X (pronounced "ten"). But that's where the positives end and the negatives begin. Segall lays out four ways that Apple is botching the new iPhone names.

That pesky "S"

Segall has long been a critic of the "S" naming convention, as it signals to consumers that the upgrades that year are incremental, implying that those iterations are less worth upgrading to. In reality, "S" years have brought about some of the most important product innovations, including Siri, Touch ID, and 64-bit processors. On top of that, Apple isn't even consistent with the "S."

Apple has used the same iPhone form factor for four product cycles now: iPhone 6, iPhone 6s, iPhone 7, and iPhone 8. What happened to 7S or 9? It makes no sense.

People still say "iPhone ex"

Over the past year, consumers have casually used "iPhone ten" and "iPhone ex" interchangeably. It gets worse when you append another letter behind a roman numeral, which just adds even more confusion. Undoubtedly, people will get "iPhone ten ess" and "iPhone ex ess" confused, as well as "iPhone ten arr" and "iPhone ex arr."

Speaking of the "R"

What does it even stand for? Segall notes that the SE in iPhone SE was ambiguous, perhaps unaware that marketing chief Phil Schiller had subsequently and quietly confirmed that it stood for "Special Edition." We didn't get any indication this time around about what the "R" even stands for.

The mystery has sparked all sorts of speculation, which is not a good thing.

Inconsistent "S" styling

Segall admits his last point could be nitpicky, but he notes that the "S" in "XS" is inconsistently stylized as a capital S and a lowercase s. (This has also befuddled your local friendly neighborhood editors.) That includes third-party ads, but we all know how controlling Apple is with its partners.

"Inconsistencies drive me crazy," Segall writes. The difference may seem insignificant to average consumers, but for marketing professionals like Segall, details matter.

Does it just get worse from here?

Only Apple and Schiller know where iPhone names go from here. Segall suspects that Apple will consolidate all future iPhone brands under the X moniker, much like it had originally done with Mac OS X (since renamed macOS). With the branding path that Apple is now on, Segall predicts the worst:

Next year, I imagine we'll see an iPhone X2.

Then, one year later, the Holy Grail of bad product naming will be within Apple's grasp. An iPhone X2S will feature a Roman numeral, a number and a letter, all in one name. Now that's a breakthrough.

This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.