Last December, I switched my personal email from Gmail to HEY. It’s been seven months, and I decided I’m due for another move. I want to summarize my decision in three posts: which part of HEY works for me, which part sucks, and what alternative I’m going with. And here’s Part I to get all the negatives out of the way: it’s all about why HEY sucks.

Part I: HEY sucks
Part II: Switching to Fastmail
Part III: My Fastmail workflow

HEY did not pass the Marie Kondo test

HEY did not spark joy. I’m sure it did it (and continues to do it) for many users, but not for me. To start, I’m sick of the cheesy “Imbox” name. HEY is so proud of this name that they bought a domain for it. But I personally find it lame and gross (and so many people would agree with me that there’s a Chrome plug-in). It’s indication of the buttload of ego that the CEO has (I have a separate writing from a while back, before I found HEY to be completely annoying).

App appearance is subjective, but there’s really nothing great about Hey. Their line of apps—Mac, iPhone and iPad—are simply wrapped web apps. It’s gross to look at. HEY’s app design is too loud. So many vibrant colours for an email app. So much use of circles and squares. The wrapped web app jumps between pages without transitions.

That dumb text editor. Anything you type on Hey on the Mac are not converted to smart punctuation. (They started doing smart punctuations sometime in the spring of 2021 on iOS.) Leading a line with an asterisk does not convert it into bullet points. Same with unordered lists. The editor’s shortcuts (if they exist at all) are not exposed to system menu on the Mac and it leaves you guessing. You can do Cmd B and I to make text bold or italic but that is about it. You’d have to do everything else with a few cursor clicks.

Even in their iOS widgets they use straight dumb single quote for empty placeholder—“There's nothing in New For You.”

The App Sucks

You can’t “Go back” from any page.¹ Click on the top left button and you are taken back to Inbox. Maybe you are viewing a list of communications from a certain sender, and you need to pop in and out between a few emails. Good luck doing that.

It takes two clicks to go from Inbox to Paper Trail.² Or to anywhere really. The HEY button is a giant hamburger menu; it just doesn’t look like a burger.

I’m sick of HEY’s sender avatars. Circles and squares in neon colours. You tap on them in different places, and different things happen. Tap it in Inbox and you enter/leave multi-selection mode. Tap it somewhere else you might enter the page listing all emails from this sender.

You cannot delete bundled emails. Like… why not? It’s a feature that I would use on a regular basis (to be rid of all those App Store Connect notifications). It’s a feature that I do not see any technical hurdles to achieve.

HEY claims you are in control but no you are not. You cannot choose which address to send to if there are multiple for one contact. You cannot choose to have notification badges. You don’t get nudged by a red dot that there are new emails in The Feed or Paper Trails. You don’t get subject-based triaging rules.

The Workflow Is Lacking

Hey has only The Feed or Paper Trails. What about “notifications” like a new log-in in your Twitter account? These are things that don’t belong to The Feed (layout suitable for newsletters) or Paper Trails (important emails stored for longevity). They also ideally shouldn’t be residing in Inbox—they arrive on a good-to-know basis. Would be nice to have an “Updates” category in HEY, too.

HEY has very limited auto-filing capabilities. You can only file based on the sender address. While people probably shouldn’t do this, they sometimes use the same address to send marketing emails and order confirmations. You can either file them into The Feed or Paper Trails, or leave them in Inbox. You cannot create a rule and auto-file based on subject keywords.

Set Aside and Reply Later are the actually two good things I like about Hey. But I don’t receive too many emails that need a reply. I also don’t mind using my note-taking app (in place of Set Aside) to store things offline.

There are also a few things I missed from the iOS mail app + a normal email provider:

• Calendar appointments found by Siri
• Auto-forwarding to Parcel App to track my shipments. Hey can either forward everything or nothing at all
• More granulr controls with auto-filing based on complex rules such as subject keywords, etc.

HEY Is Bug Bound

HEY has so many bugs as a product, and a lot of them are related to account access and data availability. Its unacceptable.

When I started using HEY, I kept getting signed out of my account on iPad and iPhone every 14 days (exactly 336 hours—if I signed in again 9am on Sunday, I could expect to get kicked out by 10am on Sunday in two weeks). Re-installing HEY did not help. They fixed it after about two months.

Around the same time, my 2FA method suddenly stopped working (I discovered that after being kicked out of my account on my iPad). I sextuple-checked my input, confirmed system clocks are up to date, used two 2FA apps, and tried on different days even. The two 2FA apps agree, and they work fine generating codes for other websites. But Hey said my code was wrong. Fortunately I was able to use one of the recovery codes to get back in and reset 2FA. It was a scary thing to have happened to an email account.

Emails in Set Aside are supposed to be cached for offline access. Some are not properly cached. Some are cached fine, but the attachments may or may not open. (We had camping confirmation emails cached in May. When we arrived in July, the attachment wouldn’t open. Fortunately the BC Parks staff was kind enough to help us look up by name.) Lesson learned: always save two copies.

Search doesn’t work properly. Searching for “registr” still gave me emails containing the word “registration” but if you type another letter, “registra” shows no results. It’s quirky to say the least. I contacted support, and, without reading carefully what I said, HEY support said that they didn’t have partial search functions yet—exactly the opposite of what I saw. But I couldn’t care less.

iOS widgets stopped taking me to the email I tapped on. They fixed it maybe a month after.

Modification to sender name does not take effect in some cases. I still have "App Store Connect" and "iTunes Store" showing up on some emails (note the straight quotes that won’t go away).

There are a myriad of layout issues. It’s a web app after all.