The Frustration of Apple Reminders: Why Can’t It Just Work?

I’ve got a love-hate relationship with Apple, and today, I’m here to air out some grievances—specifically about Apple Reminders. Now, don’t get me wrong, I’m not an Apple hater. In fact, there’s a lot I genuinely like about their ecosystem. Apple Notes? Pretty good. The operating system? Solid, though I’m not exactly the biggest fan of the whole liquid glass aesthetic in Tahoe. I rely on Apple Calendar and a range of other Apple tools that work pretty well—not mind-blowing, but functional enough.

But Apple Reminders? It feels like the neglected stepchild in the Apple family of apps. No matter how much I’ve tried, I just can’t make it work. It’s trash.

Recently, I’ve had to juggle more responsibilities while managing my business. Naturally, I thought, “Hey, why not double down and see if I can finally get Apple Reminders to fit into my workflow?” Spoiler alert: I couldn’t. Despite my best efforts—forcing myself to adapt, tweaking settings, and reviewing every nook and cranny—Apple Reminders remains a dumpster fire of disappointment.

I even spent days exploring alternatives like Trello, TickTick, ClickUp, Monday.com, and Plaky. I’m a minimalist at heart, fiercely against bloat, and I really wanted to keep things simple by sticking with Apple’s native tools. But with Reminders, simplicity crosses over into the frustrating.

Let me break down the issues:

Lack of Flexibility: Sure, I can create a to-do with a due date. But adding detailed information? Forget it. I can’t add meaningful descriptions or comments. If I need to include extra details, I have to create an Apple Note, generate a link, and awkwardly paste it into the Reminders URL field. It’s a clunky workaround at best.

Subtask Nightmares: When I flag a subtask (my version of a “do-now” list), there’s no easy way to jump to its parent task for additional context. I have to manually dig through lists to find it.

No Real Status Indicators: I’ve tried using tags, but they’re bland and uninspired—just 2000’s style hashtags with no color or standout features.

Collaboration: Adding someone to a list sounds great in theory, but they can’t comment on tasks. They can edit a reminder, sure, but if there’s an Apple Note linked, I have to send them a separate invite just to view it.

In contrast, the tool I ultimately chose: Trello, and it works. I can create a card for an overarching goal, add due dates, start dates, comments, and multiple checklists. The flexibility is seamless. Tasks don’t have to be rigid subtasks tied to dependencies. They’re just… easy to manage.

I  want Apple Reminders to work, but it’s just the worst solutions Apple has ever created.

</rant>

It wouldn’t take much to make Apple Reminders worthwhile:

Parent Task Visibility: If flagged subtasks could display their parent task or provide a quick link, that’d be a game changer.

Section Control: When adding a section, let me choose its position or set a default section for new reminders.

Consistency Across Platforms: On iOS, I can assign tasks to specific sections when creating them. Why can’t I do the same on macOS without extra clicks?

If Apple ever decides to give Reminders the attention it deserves, I’ll be the first in line to give it another shot. Until then, I’ll stick with tools that actually help me get things done.