A Financial Times investigation reveals that OpenAI's ambitious wearable AI project, created in partnership with renowned designer Jony Ive, whose work defined Apple's aesthetic for decades, is encountering substantial roadblocks as it attempts to bring the concept to market. Making dystopian AI wearables is harder than it looks.

The device takes an unconventional approach by eliminating screens entirely, instead packaging cameras, microphones, and speakers into a pocket-sized format comparable to contemporary smartphones. Conceived as a creepy ever-present digital partner, it would passively collect information from its surroundings to facilitate ongoing dialogue with users, echoing the design philosophy behind Humane's AI Pin, which, if you recall, didn't exactly set the world on fire.

Beyond keeping details under wraps, OpenAI is wrestling with fundamental technical and design dilemmas. Despite securing massive funding rounds that would make a small nation jealous, the company faces computational constraints that limit the device's capabilities. More unexpectedly, internal debates over the assistant's behavioral characteristics have become a major sticking point. Engineers are caught in a delicate balancing act: the device must offer meaningful input for daily decisions without becoming that insufferably chipper friend who won't stop offering unsolicited advice.

This personality calibration problem isn't new territory for OpenAI. Earlier iterations of its AI models developed reputations for being excessively agreeable. The AI giant also worries about scenarios where the assistant enters repetitive loops during routine activities, which would be about as useful as a GPS that keeps recalculating the same route.

To make matters worse, legal complications further cloud the project's prospects. In June, iyO, an audio technology startup backed by Google, filed a trademark lawsuit challenging OpenAI's use of the "io" branding after the company's $6.5 billion acquisition of Ive's startup in May 2025. The plaintiff argues that "io"—shorthand for "input/output"—creates consumer confusion with its own "audio computer" earpiece product, particularly given that OpenAI leadership, including Sam Altman, had previously examined iyO's technology firsthand.

Awkward.

A federal judge has since issued a temporary restraining order compelling OpenAI to scrub all "io" references from public-facing platforms and marketing content. OpenAI dismisses the lawsuit as baseless and insists the legal dispute won't derail either the acquisition or ongoing product development.

We'll see about that.