Moving from HEY to Fastmail

A few weeks ago, I decided to migrate my mails from HEY to Fastmail. The reasons were not in any way related to the quality of HEY service, in fact I was a very happy HEY user, I liked the overall flow and design, all rather simple but fitting my needs well. I had even written a series of blog posts about the cool HEY technology earlier and, as a Rails developer, I was really happy about this blow of fresh air in the front-end dev area.

But after the Basecamp affair blew up unexpected, I watched in horror all the weird moves and ”explanations“ that the Basecamp / HEY leaders committed to. I saw tragically oversized egos, willing to sacrifice almost half of their employees and a lot of their reputation for reasons that were just not worth it, to say the least. I gave it a few weeks and after I still saw no attempts of deeper reflection on their side, I decided I just did not want to support these guys for now, not even by paying for a service that I otherwise liked so much. I needed my time and money off from this.

Anyway, this post is not meant to be about ”politics“. This is an attempt to help you replicate some of the HEY mail patterns in Fastmail, regardless of the particular reasons you may have for the switch. Also, this is definitely not the only way to configure a HEY-aligned Fastmail. Some approaches have already been documented, before. This post tries to do a few things differently and is more focused on the migration process itself.

Why Fastmail? Frankly, there was no big particular reason for me. I saw it recommended often on Twitter, briefly compared its features to a few alternatives, and decided to go with it. After using HEY for a year, all other mail services just look somewhat similar to me.

The losses and gains

Be prepared that in some ways the transition will probably hurt. You’ll be moving from a mail client that deviates largely from the standards back to a more traditional setup. While Fastmail is a highly configurable service, it is not possible to mirror the HEY patterns fully and your satisfaction mileage may vary.

Some of the losses:

• The easiness of the HEY workflow: most HEY patterns can be done in Fastmail but configuring and using them is more cumbersome and usually requires a bit more thinking and mouse clicks.
• Your nice email address, if you managed to grab one in HEY (I was lucky enough to get the same local part in both services).

Some of the gains:

• Great mail filtering and rules capabilities (with HEY you only get what the authors think is good for you – or them).
• Good support for undoing things, including sending mails.
• Custom domains in the Standard plan.
• Money: Fastmail is only about half the price of HEY, or even less. (BTW, want 10% off? Use this referral link to subscribe.)
• No more cognitive dissonance if you are concerned with the recent HEY leadership affairs.
• Your Inbox will again be called ”Inbox“, just like you’d expect 🙂.

Other stuff that is important to me is about the same: both services have good security measures, good mobile apps, nice key bindings and their interfaces are fast. And, finally, there is a way back if you change your mind (see below).

Trialing Fastmail

A good time to start planning the migration more seriously is about one month before your HEY account gets renewed. Fastmail has a month-long trial, so you’ll have just enough time to test whether it suits your needs before having to pay.

To find out the renewal date in HEY, go to the ”Me“ menu ⟶ Account Setup ⟶ Billing & Invoices:

I recommend to actually try to organize your real mail in Fastmail during the trial. For this, you need to switch on mail forwarding from HEY to your Fastmail account. To do that, go to the ”Me“ menu ⟶ Account Setup ⟶ Forwarding & SMTP Setup ⟶ Forward mail out of HEY:

You’ll need to confirm this, see the instructions that HEY sent you. From now on, you’ll get your incoming mail in both services. If the traffic of your incoming mails is too low, you can also copy your older mails via a procedure described below.

Mimicking the HEY workflow

Some of the HEY features that I want my Fastmail account to mimic the most are:

• Screening, i.e. routing new senders’ mail to a folder separate from Inbox, so that it’s me who decides when to deal with them,
• The Feed as a place to occasionally read newsletters,
• The Paper Trail, a place to store mail receipts and other stuff that I need at hand but don’t want to process each time they arrive,
• and the Reply Later / Set Aside buckets with mail to return to later.

These features can be configured in Fastmail e.g. using a combination of Folders, Contact groups and Filtering / Routing rules.

Folders

I first configured three new folders to route mails into, the Screener, The Feed and The Paper Trail:

Notes on folders configuration:

• The Screener folder is automatically hidden unless there is any mail unread or unprocessed.
• The Feed folder is set to be auto-purged, I don’t need to permanently store newsletters.
• The folders have different colors to be more easily discernible.

Contact groups

Next, I created two new contact groups. These serve as ”pools“ of contacts / email addresses and mail incoming from them will be handled by the filtering rules. Contact groups allow specifying the destination folder based on the sender’s address, in the same way as it is done in HEY.

Notes on the Contact groups:

• Paper Trailers are peers (usually bots, actually) that send various receipts or other stuff that I want to get stored to the Paper Trail folder.
• The Feeders is a group of contacts that send newsletters and that I want to read in The Feed folder, occasionally.

Routing rules

Finally, so far I’ve come to the following set of rules to support a HEY-like flow in Fastmail:

Let’s dig through them:

1. This is actually an exception from later rules and I’ll explain it below.

2. – 3. These rules route emails with some generic keywords (rule #3) or belonging to the ”Paper Trailers“ contacts group (rule #2), to the Paper Trails folder. The mails are marked as read.

4. – 6. These rules handle newsletters. Typically, a newsletter will contain the list-id header and the ”unsubscribe“ word somewhere (rule #6) or the list-unsubscribe header (rule #5). If these rules fail to match a newsletter, I can put the sender to the Feeders contact group and rule #4 will route their mail directly to the Feed folder. I also want these mails to be marked as read as I don’t want to get notified about each new newsletter.

7. Finally, new mail from unknown senders will get routed to the Screener folder.

Now, back to rule #1: if some of the rules directs a message to one of the special folders but I want it to go to Inbox instead, I can create an exception like this. In particular, this rule stores my mail notifications from GitHub to the Inbox, as opposed to saving it to the Feed folder.

Migrating data

Now it might be a good time to actually migrate your data between the services. We’ll migrate the contacts and – of course – the mails.

Migrating contacts

This one is easy. In HEY, go to the ”Me“ menu ⟶ Account & Setup ⟶ Export your data and click Export my contacts.

The downloaded VCARDs file can be re-imported in Fastmail, here: Settings ⟶ Import & Setup ⟶ click Upload Address Book File. And voilà, you have your contacts ready.

You might also want to assign some of the contacts to their corresponding Contact groups introduced above.

Migrating mails

Update as of September 2022: this section describes a rather cumbersome process of migrating HEY mails using a local Thunderbird mail client. Luckily, none of that is necessary any more as Fastmail now directly supports importing MBOX files! To migrate HEY mails, export them to an mbox file (see step 1. below) and then just go to Settings ⟶ Import in Fastmail and upload the file and you should be good!

I’m leaving the original section text for reference but note that only step 1 is needed now.

Original section text follows:

Unfortunately, migrating mails is not as straightforward as contacts, because Fastmail allows importing mails via the IMAP protocol and HEY does not support IMAP.

However, there is a three-step migration path available:

1. Export your HEY mail to a local file in the mbox format: go to the ”Me“ menu ⟶ Account & Setup ⟶ Export your data ⟶ click Export my emails. Give it several minutes to process and download the file.

2. Now, import the backup file to a Local Folder in the Thunderbird application:

   • Install Thunderbird on your computer.
   • In Thunderbird, you need to install the ImportExportTools NG add-on: go to the main menu ⟶ Add-ons ⟶ search for "importexport" ⟶ click Add to Thunderbird on the add-on page.
   • Now, right-click the Local Folders ⟶ ImportExportTools NG ⟶ import mbox file ⟶ import directly one or more mbox file ⟶ OK:
   • It shouldn’t take long before you’ll see all your HEY mails in the Local Folders:

3. Finally, move the local mails to your Fastmail account via the IMAP protocol:

   • Create a new app password in Fastmail for the Thunderbird IMAP access: Settings ⟶ Password & Security ⟶ Manage App passwords ⟶ New app password ⟶ choose Custom and fill-in something like "Thunderbird" ⟶ choose "IMAP" for the access type and finally click on Generate Password.
   • Set up a new IMAP account in Thunderbird: go to Set Up Another Account ⟶ Email ⟶ fill in your name, your Fastmail mail address and copy the app password generated in the previous step to the Password field. In the next step, the server settings will be hopefully auto-guessed (if not, follow the settings shown here) and you’ll have your Fastmail account available in Thunderbird.
   • OK, now, in the Local Folders, select all mails and drag-and-drop them to the Fastmail account. This operation will take time, a lot of time, depending on the size of your mails and network speed. In my case it took around an hour to move all mails.

Tidying up

After the migration finishes, chances are that some of your mail got into your Inbox instead of the Feed or Paper Trail. This is a nice opportunity to cultivate your filtering rules.

To make sure that a rule applies to all migrated mail, just edit the rule: Settings ⟶ Filters & Rules ⟶ Edit a rule ⟶ optionally amend the definition ⟶ click Preview ⟶ review that the proper mails are selected ⟶ click Update Rule ⟶ select the Apply to all XXXX matching conversations now and hit Save. The rule will be reapplied to all the relevant mails:

You might also want to mark all your migrated mail as read — after all, you’ve already read it in HEY, haven’t you?

Finally, you can now safely delete the imported Local Folder as well as the IMAP account in Thunderbird (and even uninstall the program) if you like. Ideally, don’t forget to also delete the app password for Thunderbird access in Fastmail generated above.

The workflow

Screening

New mails from unknown senders arrive to the Screener folder. This folder is normally empty and hidden so when you do see it, it means there is something waiting patiently for your attention. You basically have two options now:

1. Add the sender to your contacts so that future mails from them will arrive directly to Inbox: click Add to Contacts in the Sidebar. Optionally you may want to set the proper contact group if you wish this sender’s mail to go to the Feed or Paper Trail.

2. Or permanently block mails from the sender: click More ⟶ Block ”the sender“.

Now that you have the future all set with this sender, you still need to move this first message to the proper folder or delete it. I really recommend learning the Fastmail keyboard shortcuts as they speed things up tremendously.

Reading the Feed and the Paper Trail

Not much to say here, new mail just arrives to these special folders. It is automatically marked as read so that you are not notified about each new message in them.

Time to time, however, you may find a mail here that belongs somewhere else. That’s most probably because it matched one of the generic rules via a keyword or a mail header. That’s not a big deal in Fastmail, you just have to create an exception rule, similar to the rule #1 above. You can conveniently use the Add rule from Message option in the message menu for this:

Setting mails aside

The Set Aside / Reply later function in HEY makes the selected messages permanently visible in your inbox. There are a few approaches available to mimic this in Fastmail:

• One of them is message pinning. You can pin any message to set it aside from the normal flow. To be able to find it again later, you can save a custom advanced search (called e.g. Set Aside) that will filter only pinned messages by searching for "is:pinned".

  

• If viewing custom search feels too cumbersome, you can have your Inbox sorted in a way that keeps the pinned messages above the rest: click the Sort menu ⟶ Keep pinned on top. Fastmail remembers this setting separately for each folder.

  

• Or, if you’re like me, you can give up on pinning messages completely and resort to archiving all other messages instead. As a bonus, you’ll have a clean Inbox with only the messages that you currently deal with visible. This is a pattern somewhat similar to using the Cover Art feature in HEY, only cleaner and less personal, of course. The keystroke for archiving mail is "H". I like this option the best.

Canceling HEY and the loophole option

OK, are you comfortable enough with Fastmail? Don’t forget to actually cancel your HEY account! To do this, click the ”Me“ menu ⟶ Account & Setup ⟶ Billing & Invoices ⟶ click Cancel your subscription and confirm. Bye, HEY! 👋

Oh and if you’re in a bit of an activist mood, don’t forget to tell HEY why you’re leaving, they have a nice little feature just for this:

Should you ever want to switch back to HEY after your (paid) account expired, you will be able to get your previous HEY address that you’ve paid for. I have this fact confirmed by the HEY support. You’ll probably need to write them from the forwarded mail address to prove ownership.

However, as HEY does not support importing mail in any way, you’ll have to keep all the mail from your Fastmail era somewhere else…

Also note that, unfortunately, Fastmail does not keep your email address and is OK with reselling it after you cancel your account so you may have to pay an extra year there to make sure you notify all your senders properly about your new / restored address.

Final words

After using the patterns described here for a few weeks in Fastmail, I can confidently say that it is a very livable option for me. I loose some of the elegance and personal touches typical for HEY but in the end it works about the same and I actually feel somewhat more — free — than before. I think I don’t necessarily have to adore my email service, after all, I can just, you know, use it again. 😄

Good luck with your own attempts to make the switch! I’ll love to hear about your experience in the comments. And follow me on Twitter if you like reading stuff like this. 🤞