HEY Email: Brilliant Reinvention or Overpriced Experiment?

When HEY launched, I was genuinely excited.

Email has needed a rethink for years, and here was a company saying, “What if the problem isn’t spam — what if the problem is email itself?”

I signed up early. I used it properly. I tried to commit to doing email “the HEY way.”

For a while, it felt refreshing.

But over time, I found myself drifting back to more traditional tools — not because HEY failed at what it set out to do, but because it succeeded in a way that doesn’t work for everyone.

When HEY first launched, it even sparked an App Store dispute with Apple over in-app subscription rules — a public fight that highlighted how different the product’s business model was compared with traditional apps like Gmail or Outlook.

To understand HEY, you have to understand the company behind it.

Why I’m writing this now

This article actually started with a reader comment — and I genuinely love getting messages like this. Hearing how people are using these tools — and questioning my past opinions — is one of the best parts of writing this site.

On my Gmail vs Proton Mail post, a subscriber wrote:

“I was skimming through your blog and apparently missed something. You used to be so enthusiastic about HEY, but that’s no longer the case? Have you switched to Proton since then? What was the reason for that? Perhaps you could dedicate a post to this sometime.”

Fair question.

When HEY first launched, I really liked what they were trying to do. It felt fresh, thoughtful, and brave in a space that usually just copies Gmail. I used it seriously for a while. I paid for it. I recommended it.

But over time, my view changed.

Not because HEY got worse.

But because I realised it wasn’t built for how I actually use email day to day.

This article isn’t a takedown, and it’s not a fan piece either. It’s a reflection on what HEY does brilliantly, where it falls short for some people, and why a bold reinvention of email turns out to be both its biggest strength and its biggest limitation.

If you’ve ever wondered whether HEY is a glimpse of the future — or just an expensive side path — this is for you.

The company behind HEY matters

HEY comes from 37signals, the team best known for Basecamp — a product that built a loyal following by doing things differently and refusing to follow industry trends.

37signals has always designed software around strong opinions:

• Fewer features
• More clarity
• Less customisation
• The belief that most tools are bloated

HEY is email built with that same philosophy.

But 37signals also has a history of building bold products — and sometimes moving on from them when they no longer fit their direction. They are not a company that iterates endlessly to please every edge case. They build what they believe in, and if it stops fitting, they move on.

So when you use HEY, you’re not just trying a new email app.

You’re stepping into a deliberately constrained system, shaped by a company that believes software should guide behaviour, not just accommodate it.

That explains why HEY feels so different — and why that difference can feel either brilliant or frustrating.

HEY doesn’t improve email — it redesigns it

Most email providers try to compete on:

• More storage
• Better spam filters
• Faster search
• More integrations

HEY ignores almost all of that.

Instead, it asks a more radical question:

What if you didn’t have to receive every email people send you?

That idea becomes the foundation of HEY’s most famous feature.

The Screener: a gatekeeper for your inbox

With HEY, the first time someone emails you, their message doesn’t just land in your inbox.

You have to approve the sender first.

It’s like a gatekeeper for your email address.

Once approved, future messages go through normally. If not, they stay out.

It’s a clever system. It gives you a feeling of control that traditional inboxes rarely do. And in the early days especially, it feels almost magical to see your email become quieter by design.

But there’s a trade-off:

You are now responsible for managing that gate.

And email — for all its flaws — was built to be open and frictionless.

For some people, the Screener feels empowering. For others, it feels like one more system to maintain.

Systems that gate new senders aren’t new. Older tools like challenge–response filters and email whitelists tried similar ideas years ago — but they were technical, clunky, and often pushed the burden onto the sender. HEY is different because it turns that old concept into a polished, user-controlled experience built directly into the inbox.

The Imbox, the Feed, and the Paper Trail

HEY doesn’t just filter spam. It reorganises email into new categories:

• The Imbox – for personal, important conversations
• The Feed – for newsletters and updates
• The Paper Trail – for receipts and transactional mail

This structure is thoughtfully designed. It separates “things to read,” “things to skim,” and “things to keep for records.”

In practice, though, it requires you to trust HEY’s model of your digital life. You don’t get the same flexibility or deep custom rules you might expect elsewhere. You either adopt their system, or you constantly feel like you’re working against it.

That’s very 37signals. It’s opinionated on purpose.

More than an inbox: HEY’s extra features

Over time, HEY has added more than just inbox filtering:

• Reply Later and Set Aside for lightweight task-style email management
• Bubble Up reminders to bring emails back when you’re ready
• Clips and Sticky Notes for saving key parts of messages
• A built-in calendar and journal, extending HEY beyond email
• Tracker blocking by default to limit hidden email surveillance

None of these are designed to compete feature-for-feature with Gmail or Outlook. They’re designed to support HEY’s central idea: email should feel calmer and more intentional.

Some people love that. Others find it limiting.

HEY World is a genuinely great idea

One part of HEY that really stood out to me was HEY World.

The idea that you can send an email and have it published as a simple, clean web post is brilliant. It lowers the barrier to sharing thoughts online and makes writing feel more casual and direct.

It’s one of the few email-adjacent features I wish more platforms would copy.

It shows that HEY isn’t just trying to fix inboxes — it’s trying to rethink how email fits into communication more broadly.

The design is confident — and divisive

HEY doesn’t just rethink how email works. It makes bold design choices everywhere.

The colours are loud. The layout is distinctive. The language inside the app is playful and opinionated.

Even the logo makes a statement — and I’ll be honest, I’ve never liked it. It feels more like a brand for a kids’ app than a service managing important parts of my digital life.

That doesn’t make it bad. It just reinforces something important:

HEY is not a neutral tool trying to fade into the background.

It’s a product with a strong personality.

A closed system by design

One of the hardest adjustments for me was how self-contained HEY is.

• Limited IMAP/SMTP support
• No broad ecosystem of third-party clients
• Workflows built around HEY’s own interface

This isn’t an accident. It’s a deliberate choice to control the experience end to end.

Upside: Consistency. Simplicity. Cohesion.

Downside: Less flexibility. Fewer ways to connect with other tools. More lock-in.

If you live inside HEY, it works. If your email life touches lots of other tools and systems, it can feel restrictive.

The price question

HEY is not cheap.

Compared to other email services that offer custom domains, large storage, advanced security features, and broad compatibility, HEY’s pricing feels steep.

For context, services like Fastmail start at around $5 per month, and Proton Mail plans start at roughly $3.99 per month. Both focus heavily on flexibility, traditional email workflows, and (in Proton’s case) stronger privacy architecture.

HEY isn’t really competing on storage size, protocol support, or deep security tooling.

You’re paying for a philosophy, a controlled environment, and a reimagined workflow.

For some people, that experience-first approach is worth the premium. For others, especially those who just want powerful, secure, and flexible email, it can feel like an expensive experiment.

Here’s how that trade-off looks at a glance:

HEY Email at a glance

Who HEY Is For

HEY is a great fit if you:

• Feel overwhelmed by traditional inboxes
You like the idea of email being permission-based, where you decide who gets through.

• Appreciate opinionated software
You don’t want endless settings — you want a system that’s designed on purpose and pushes you into better habits.

• Mostly use email through a single interface
You’re happy living inside one app and don’t rely heavily on third-party clients, complex rules, or external integrations.

• Value calm over control
You prefer a quieter, curated experience even if it means giving up some flexibility.

• Enjoy thoughtfully crafted tools
You notice (and care about) writing tone, interface personality, and product philosophy.

Who HEY Is Not For

HEY will likely frustrate you if you:

• Use email across many apps and systems
If your email is tied into other apps, custom workflows, or multiple clients, HEY can feel restrictive fast.

• Want granular control
Power users who rely on filters, folders, rules, and technical setup options may find HEY limiting.

• Prioritise advanced privacy architecture
If your definition of “secure email” includes end-to-end or zero-access encryption, HEY isn’t designed around that model.

• Prefer tools that adapt to you
HEY expects you to adapt to it. If that sounds annoying rather than refreshing, it’s probably not your fit.

• Are price-sensitive
You can get highly capable email elsewhere for less money if HEY’s philosophy doesn’t strongly appeal.

HEY isn’t trying to be the universal email solution. It’s trying to be the right solution for a specific kind of user — and that clarity is both its strength and its limitation.

You don’t lose your address if you leave

One detail that often gets overlooked:

If you cancel your paid subscription, you can usually keep your @hey.com address and forward it elsewhere for free.

That’s rare — and genuinely generous. Most paid email services tie your address to your subscription. Stop paying, and the address often disappears with it.

With HEY, you’re paying for the experience and tools, not permanent ownership of the address itself. In practice, that lowers the risk of trying it.

I still occasionally receive email to my old @hey.com address, quietly forwarding on in the background. It’s a small thing, but it reinforces the idea that HEY isn’t trying to trap your identity — just rent you a particular way of doing email.

Security: solid, but not revolutionary

HEY positions itself as privacy-respecting, but security isn’t the core lens through which the product is built.

That doesn’t mean HEY is careless. It uses modern protections: encrypted connections, strong account security practices, and a company culture that clearly values user trust. Your data isn’t being mined for ads, and the business model is straightforward — you pay for the product, not with your attention.

But HEY’s architecture is very different from providers that design themselves around minimising what the provider can see.

With HEY, email is processed server-side in order to power features like:

• The Screener
• The Imbox/Feed/Paper Trail sorting
• Search and organisational tools

That means HEY, like most traditional providers, technically has the ability to access stored message content if required for operations, troubleshooting, or legal compliance.

Compare that with services built around end-to-end or zero-access models, where:

• Message content is encrypted in a way the provider cannot decrypt
• The system is intentionally designed to limit what the service itself can see

Providers in that category focus on cryptographic boundaries as a core feature. HEY focuses on experience boundaries — controlling who gets into your inbox, how messages are categorised, and how email feels to use.

Those are different philosophies.

HEY tries to make email feel better. Some competitors try to make email mathematically harder to access.

If your top priority is:

“I want the provider to be technically unable to read my stored email,”

HEY isn’t built around that goal.

If your priority is:

“I want fewer unwanted messages and a calmer inbox experience,”

HEY’s approach to control and filtering may feel more impactful day to day than deeper encryption models.

In short, HEY treats privacy as a matter of business model and product integrity, while some competitors treat it as a matter of cryptographic design constraints.

Neither approach is inherently wrong — but they solve different problems.

So… brilliant reinvention or overpriced experiment?

Honestly, it’s both.

HEY is one of the few serious attempts to rethink email, not just optimise it. It questions assumptions most providers take for granted and turns inbox management into something more intentional.

But that reinvention comes with constraints:

• A closed ecosystem
• A workflow you must adapt to
• A price that’s hard to ignore
• Security that’s good, but not leading-edge

I’m glad I used HEY. It changed how I think about email.

But I realised something important:

I didn’t just want email to be different.

I wanted it to be different without cutting me off from the rest of the email world.

Would I give HEY another shot?

Honestly… maybe.

Even though HEY didn’t stick for me long term, I still respect what they tried to do. It takes guts to look at decades of email habits and say, “Nope — we’re redesigning the whole thing.” Most providers just add features. HEY rebuilt the experience from the ground up.

Some parts genuinely worked well for me:
• The focused, calmer interface
• The way HEY forces you to decide who’s allowed into your inbox
• The thoughtful touches like The Feed and Paper Trail
• And yes — the support, which felt human and fast when I needed it.

But the same things that make HEY special are also what make it hard to live with:

• It’s a closed ecosystem with strong opinions about how email should work
• You can’t easily bend it to your habits — you have to adapt to theirs
• The pricing feels high when you compare it with more flexible providers
• And if you rely on traditional email workflows, HEY can feel like friction rather than freedom

So would I try it again?

I’d never say never. If HEY softened some edges, worked better with other email tools, or adjusted pricing, I’d be curious. I still think it’s one of the most interesting experiments in email in the last decade.

But right now, security and control over how my email is structured matter more to me than a beautifully opinionated environment.

HEY is bold. It’s different. It’s memorable.

It’s just not the email home I ended up choosing.