Why I'm Leaving Hey and Returning to Fastmail

Pros and cons of Hey.com and why I'm switching back to Fastmail.

June 11, 2024

I was an avid Gmail user for almost a decade. But, just like DHH is starting to object against Apple, I've had similar disagreements with Google. So, I went looking for alternatives.

In January, I signed up for Hey. I was excited to try it out and impressed by the team behind it. But, after a year of using it, I'm switching back to Fastmail. Here's why.

One Size Doesn't Fit All

Undoubtedly, the team behind Hey includes some highly talented engineers. The platform has much to offer and is probably perfect for some people. My opinions are my own and don't necessarily mean Hey won't be a good solution for you.

My Experience with Hey

I love the "screened out by default" concept. The idea is that only the emails you want get through to your inbox, or "Imbox," as Hey calls it. This sounds fantastic in theory, but in practice, it meant that I had to check three separate inboxes: the Imbox (including emails that have been "screened in"), the Paper Trail (which includes receipts but also important time-sensitive emails), and the First-Time Senders list, which might have essential emails as well.

In a perfect world, the Paper Trail would only include receipts or receipt-like emails. Understandably, it can't determine if an email from your bank is a receipt, unwanted marketing, or a security alert. To me, that's a deal-breaker. Filtering based on the sender's email address is a good idea, but it could be better.

Down the road, I would love to see a privacy-focused AI approach rather than simply using the email address. This would also help with spam, as spammers regularly cycle email addresses and end up filling the First-Time Senders list, which, again, you have to check regularly to avoid missing an important email.

The Somewhat Clunky Interface

In the end, I spent more time checking my email because I had to transition between these lists with what is, in my opinion, a clunky interface. On the desktop, the keyboard shortcuts help immensely, but that doesn't help on iPhone. On iPhone, you need to tap the "Hand" icon, then tap the category you want to view. This gets annoying quickly.

In my opinion, the worst part was categorizing First-Time Senders in one of the categories. You have to tap this tiny down-arrow icon and then select the category for every sender. On the iPhone, this was tedious and error-prone. Hey should take a cue from Apple and have swipe gestures on this screen (like they do on other screens) on the iPhone. And maybe dedicated buttons on the desktop.

A screenshot of the tiny 'Deliver to This Category' button
Clicking 'Yes' sends future messages from this sender to your Imbox. Clicking the tiny down arrow lets you choose a different category.

Apple Stepping Up

Apple introduced many features on iOS 18 that cover all of the benefits of using Hey, such as categorizing emails and filtering by "important senders."

In fact, the three headlines from Hey.com are all covered with Apple's updates to Mail in iOS 18:

  • Screen emails like you screen your calls: Apple introduced on-device email categorization, which seems to have all the benefits of the split-inbox approach Hey uses.
  • The Imbox is for your important mail: Apple's new Primary category should handle this.
  • A paper trail for receipts and transactions and "The feed is for your casual, whenever reads": Apple introduced Transaction and Updates categories.

Of course, iOS 18 won't launch until this fall, so time will tell if Apple's implementation is up to par.

The Hey Calendar

The Hey Calendar was absolutely bonkers to me. Why on earth would I ever want my calendar events to appear with their text rotated, like in the "timeline-based day view" that looks like a filmstrip? From what I could tell, there wasn't a way to disable this and go to something more standard.

A screenshot of the strange (to me) Hey Calendar day view

Unnecessary Features

Some built-in features, like time tracking and calendar pictures, felt really out of place. Some people may want this, but it didn't appeal to me.


In conclusion, I'm switching back to Fastmail for my provider and Apple Mail for my client. It's privacy-focused, simple, and blazing fast with swipe gestures. And I can read my day calendar without tilting my head.