Hello Email Gripes With HEY and Fastmail

Tasos Sangiotis
Nov 29, 2020 · 5 min read

It all started with HEY. There was so much buzz around it. It is made from the company behind Basecamp 3. I use Basecamp and it is great so I decided to try it.

It offers a two week trial which is more than enough to judge if an email service for $100/year is worth the trouble.

Warning: This will be very boring for most. My personal email setup is a dull matter. It might however be useful for some as it solved some problems for me.

I also include a mini review of Basecamp’s HEY mail service. It wasn’t for me in it’s whole but it made me think how I use email and triggered a change. This is powerful and I recommend you try it for your self.

My initial impressions were great.

I loved The Feed and The Paper Trail sections. This distinction seems to solve the multiple folders and elaborate rules that dictated my inbox. Just enough delegation.

Amazing interface. It is fast and easy to use. No hidden stuff and not many options.

The screener is very original. Great idea and I don’t understand why anyone hasn’t thought of it. You greenlight only the people or services you want in your inbox.

Merging and renaming email threads is awesome! I can see the potential there. Multiple threads for the same thing become one package.

Focus & Reply would be great if I could use it with my work address. Since HEY doesn’t support using your work address with it I haven’t tried.

HEY is an opinionated service. It is part of its charm but sometimes it causes some problems.


The problem is that it is based on the email sender without the email context. You select what happens with all the emails from that sender. Myself, I need the receipt to go to the Paper Trail but the “Your password has been changed act if this was not you” notification to my Inbox. Sometimes this information comes from the same email address and I can’t blame the sender for that.

You can through all the Paper trail emails in your Imbox and triage them later but depending on the situation this might defeat the purpose.

This system made me anxious that I was missing email. This is the opposite than advertised calm effect where I should now check three Inboxes instead of one.

Yellow pages

One is you can avoid dealing with contacts on HEY. This makes core features like the contacts page loose value. This happens because some people have more than one email address they use be it personal, professional and now a HEY trial. If you don’t cater to organize those, every email goes to a different contact for the same person so at the end you don’t have all of their emails organized.

Your other option is to maintain multiple contact systems. One that is the main one and syncs with your phone and another one for HEY. This is too much work for a service that costs $100/year.

Identity crisis

This is scheduled to change but it will cost more and I cannot buy software with promise of support in the future.

What now?

The thing is I liked HEY’s approach. It is basically a framework for email. And this can be replicated.

At the same time I am always looking to avoid Gmail’s apps on anything but the web. They make advertisements look like normal emails on mobile. In a rush you open one of those and all of a sudden you look at a grocery store website instead of your emails.

I tried to setup Apple mail to work with Gmail but it is a nightmare because of their custom IMAP implementation.

I should be able to find something that both works and can fit my very basic in my opinion requirements.

Gotta go Fast

For that price it supports importing of my work email and sending emails from it.

I don’t fancy the iOS app but Fastmail supports open standards perfectly. It syncs with Apple mail via IMAP and it supports sending from my work address. Contacts and calendars also sync with iOS devices perfectly and setting this up was a breeze.

On the Windows desktop I use the web interface which is awesome and fast.

Already the experience is much better than Gmail for me.

Saying HEY inside Fastmail

First The Feed. I need all newsletters to go to a specific IMAP folder.

Fastmail has support for very powerful filters. More powerful than Gmail.

HEY uses a list of senders that go to The Feed. As I mentioned this causes some problems and without the screener it would require a lot of work to make that list.

A smarter way is to filters for emails with the Unsubsribe Header and move those messages on the Feed folder on arrival. As a bonus, I set a 60 day purge policy for that folder to keep things neat. After two months. The News in Newsletter has expired.

We need to set exceptions though. Basecamp, Github and other services have an Unsubscribe header for notifications but I need them to go to my Inbox.

To combat that I add them to my contacts and to a Notify group. Then I exempt their emails from the filter and as a result they meet my Inbox.

For the Paper trail I created another folder. All receipts, travel and transactional emails I manually drop there.

Also I created a Later folder to put emails that I may take some time to respond to.

Now the inbox has the important emails I deal with at the present time. Any new emails come there and when I have time I triage them. This is very easy with all the newsletters out of the way.

After a week I can say I like my workflow better.

Before dismissing HEY, keep in mind that it is a new product and many people love it. Expect it to grow into a practical alternative. I urge you to try HEY if you can. I believe its new take on email is worth exploring. It helped me reconsider how I deal with email.

If though you like open standards and traditional powerful email use try Fastmail.

Update: Despite all of the above, myself I paid for it. I believe this new take should be supported and I want to watch it’s story evolve.


Find out what others have already figured out. Follow our publication to join our community.

Sign up for Curious Hits

By Curious

Find out what others have already figured out. Subscribe to receive top 10 most read stories of Curious — delivered straight into your inbox, once a week. Take a look.

By signing up, you will create a Medium account if you don’t already have one. Review our Privacy Policy for more information about our privacy practices.

Check your inbox
Medium sent you an email at to complete your subscription.

Tasos Sangiotis

Written by

Technology @arpedon , photography and writing



A community of people who are curious to find out what others have already figured out // Curious is a new personal growth publication by The Startup (https://medium.com/swlh).

Tasos Sangiotis

Written by

Technology @arpedon , photography and writing



A community of people who are curious to find out what others have already figured out // Curious is a new personal growth publication by The Startup (https://medium.com/swlh).

Medium is an open platform where 170 million readers come to find insightful and dynamic thinking. Here, expert and undiscovered voices alike dive into the heart of any topic and bring new ideas to the surface. Learn more

Follow the writers, publications, and topics that matter to you, and you’ll see them on your homepage and in your inbox. Explore

If you have a story to tell, knowledge to share, or a perspective to offer — welcome home. It’s easy and free to post your thinking on any topic. Write on Medium

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store