As the new year dawned, expectations were high for a new calendar app from Hey. However, Apple threw a curveball just 72 hours after Hey announced its latest feature—a built-in calendar. Co-founder David Heinemeier Hansson received disappointing news: Apple rejected the standalone iOS app for Hey Calendar due to restrictions on non-paying users.

Hey, the premium email service, requires users to sign up through a browser, a practice that clashes with Apple’s App Store rules demanding paid services to offer in-app sign-ups, guaranteeing Apple a 30 percent cut. This rule has sparked antitrust debates globally, with exceptions made for reader apps like Spotify and Kindle. Interestingly, this rejection echoes a four-year-old incident when Apple blocked Hey’s original iOS app for similar reasons.

In 2020, Hey successfully navigated a similar dispute with Apple. Following a back-and-forth with the App Store Review Board, Hey agreed to a unique solution proposed by Apple executive Phil Schiller. The iOS app would have a free option, allowing direct sign-ups, but with a twist—users received a free, temporary randomized email address for 14 days, after which they had to pay to continue. Apple subsequently amended its rules to exempt free companion apps for certain paid web services from in-app payment mechanisms.

Despite this past resolution, Apple’s recent rejection of Hey’s standalone calendar app has reignited tensions. Apple contends the app “doesn’t do anything” because users must log in with an existing account to access functionality. Hey claims this rejection caused a 19-day delay, causing them to miss the planned January 2nd launch.

Heinemeier Hansson vows that Hey will challenge Apple’s decision, although the specific strategy remains undisclosed. The clash raises questions about the consistency of Apple’s App Store policies and whether they adequately address the evolving landscape of app development.