Migrating from HEY Mail to Fastmail: My Guide For a Smooth Transition

Why I decided to leave HEY Mail

I started using HEY Mail in July 2020, right in the COVID-19 pandemic. It was a refreshing albeit controversial take on emails by controversial founders. As I wrote here, my primary motivation for paying for email was to use a converged and unified mailbox for my Google, iCloud and, believe it or not, Yahoo email accounts. HEY Mail had features like Paper Trail and The Feed that made a difference for me. I still love those features, but something else drove me away from HEY Mail: the CEO and founder of 37Signals, the maker of HEY Mail (and Basecamp, another controversial product). As I wrote here, recent articles shared by DHH triggered me to reconsider my HEY Mail usage. This article is not about revisiting past controversies. It is about sharing my experience and details about migrating to a new unified mailbox: Fastmail. My goal with this article is to help others understand that migrating off HEY Mail is not as complicated as it seems by explaining how I did it.

In the coming sections, I explain how I migrated from HEY Mail to Fastmail without losing HEY Mail features: unified inbox, the Feed, the paper trail, and the screened-out mail filtering. I’ll also explain how I overcame a few unexpected challenges and share details about the many benefits of this migration. Let’s dive in, shall we?

The migration strategy

Before migrating, I wanted to buy a new domain name for use with Fastmail. After spending some time with Cloudflare’s domain name search, I finally settled on a simple one. That domain could be used in addition to the one I get by subscribing to Fastmail. I selected fastmail.ca (instead of .com) because it clarifies that I’m a Canadian. Now that I have a brand new domain name for my new email home, it’s time to move to the next step, starting the migration process.

The migration strategy was simple: migrate my less-used email accounts first (Yahoo) to test the entire migration process without affecting my daily email usage. For each migrated email account, email forwarding was disabled both at the source email account and within the HEY Mail configuration. Then, the next email account to migrate was Google’s Gmail. It’s also important to note that the goal was not to close my Google account but to migrate my Gmail account content. Making a difference between an authentication account and the email service that might be tied to it is essential. The “Sign in with Google" and “Sign in with Apple” are still part of my daily digital life. I have always preferred to use “Sign in with Apple” over Google’s offering. However, there are services that I cannot let go of that are tied to my Google account. The other important thing to consider is that I only focus on email migration. I prefer to keep those under Apple’s iCloud umbrella, just like I’m not migrating my notes from Apple Notes to Fastmail’s notes. My calendaring needs are fulfilled with Apple’s Calendar, which is stored in iCloud.

Migrating an email account involves different steps and configuration details. Just like when I migrated to HEY Mail in 2020, the same strategy applies here: I chose not to delete emails from the original mailbox; I’m only forwarding them to the unified mailbox. Also important: being able to send an email under one of my email account is essential too. I rarely used my unified email address when writing emails. Fastmail, just like HEY Mail was, is only used a single place to read and write emails, nothing more, nothing less. You might have another strategy and Fastmail will probably be able to support your use case. For example, you might want to delete the original email and keep everything inside Fastmail. That’s fine too. Fastmail is very flexible.

Importing an email account is relatively simple: you select the service provider, authenticate with the service and then select how to proceed. My migration is based on importing the email, and enabling email composition from the source account (which requires credentials). For iCloud accounts, an app-specific password must be created first. The reason is simple: you don’t need to provide the entire email and password credentials for this to work, only an app-specific password which is a little more secure.

Migrating a custom email domain out of iCloud+

Fastmail offers a simple way to use a custom domain for your email account. Because of this, I decided to migrate my hello@numericcitizen.me email address hosted on iCloud+ to Fastmail. You didn’t you know that you can use iCloud+ with a custom email domain? Yep, that's right, but migrating this email address to Fastmail was a bit challenging because custom email domains with iCloud+ are managed only on the iCloud website. If you happen to use Advanced Data Protection too, this is where it becomes tricky.

Having Apple Advanced Data Protection (ADP) is cool and nice but can make managing iCloud+ Custom domains a pain. As a reminder, to use ADP, you must turn off iCloud web access. As soon as this is turned off, you can no longer manage your iCloud+ custom email domains. To complete my migration to Fastmail, so that I could write and respond from that custom email address from Fastmail, I first had to remove that domain from iCloud+, but it's only possible on the iCloud website. To do that, ADP must be turned off. Once done, I can re-enable iCloud website access, then remove the custom email domain. After some cleaning up of Apple-related DNS records at my DNS registrar, I can re-enable ADP and disable iCloud website. Only then I can go on Fastmail Settings and configure my custom email domain for use within Fastmail.

In summary, here are the required steps

1. Disable Advanced Data Protection
2. Re-enable iCloud web access
3. Login to icloud.com and remove the custom email address.
4. Remove any Apple-related DNS records from your custom domain on your domain name provider (it should be about ive entries)
5. Disable iCloud web access
6. Re-enable Advanced Data Protection
7. On Fastmail, add your custom domain and add the DNS records as required by Fastmail
8. Next, on Fastmail custom domain panel, add an alias for the portion before the “@“ sign.
9. Wait about an hour (depending of the DNS zone TTL value which often defaults to one hour)
10. Your custom mail domain is now operational under Fastmail hosting services!

At this point, you can use your custom domain name email with Fastmail. Now, when writing an email in Fastmail, I can select to send it from five different email addresses.

Using Fastmail labels

Fastmail offers two ways to organize emails: by using folders or labels. You can switch between the two at any time. I decided to use labels, which Apple Mail doesn’t provide, but HEY Mail did. Labels are essential to Fastmail, especially when creating email rules and automagically doing stuff with each incoming email. I depend on Fastmail labels to replace HEY Mail Screener and Paper Trail. By using labels in combination with Fastmail Contact Groups, it does the trick of replacing one of the most valuable features of HEY Mail. Here is how I did it.

The first label use case is to assign a label on each email to identify their source account. This way, I can quickly see all the emails coming from my Gmail or iCloud. The other use case is for marking all the imported emails from the HEY Mail account when I imported the mbox file. Now, keep reading to learn about my HEY Mail import experience.

Importing email archives from HEY Mail mbox files

Even if my HEY Mail account contained duplicates of all my source email accounts, I exported my data from HEY Mail to import the data into Fastmail. The process is simple but took a while to complete, both on the HEY Mail and Fastmail sides. I had 2.8 GB worth of emails (close to 20K, to be precise). The idea is to have one place to search all my email archives. I wasn’t sure how my emails would end up in my Fastmail account, but thankfully, the import panel lets you select a label to assign for each imported email. The one downside of this migration is that the Imbox, Feed and Paper Trail containers are lost: all emails are tagged with the same label. The problem is not on the Fastmail side: HEY Mail should have provided a way to export those in separate mbox files. Beyond that issue, all my emails were imported flawlessly in about an hour.

Which email service supports exporting data in mbox files?

Several email services and tools support exporting data in MBOX file format. Here are the most notable ones:

• Gmail: Gmail allows users to export emails in MBOX format via Google Takeout. This is a free and straightforward method to download all or selected emails from your Gmail account.
• Apple Mail: If you use macOS, Apple Mail provides a built-in feature to export mailboxes directly to MBOX format. This is ideal for small inboxes and ensures data security.
• Thunderbird: Thunderbird, an open-source email client, supports exporting emails in MBOX format for any email provider. It works on macOS, Windows, and Linux, making it a versatile solution.
• Office 365 (via Thunderbird): While Office 365 doesn’t natively support MBOX exports, users can set up their accounts in Thunderbird and save emails as MBOX files. Alternatively, third-party tools are available for this purpose.
• https://www.systoolsgroup.com/how-to/export-gmail-emails-to-mbox-file-stepwise/
• https://www.goodbyemail.com/how_to_export_any_email_inbox_to_mbox
• https://itsupport.umd.edu/itsupport/?id=kb_article_view&sysparm_article=KB0011940
• https://support.apple.com/en-ca/guide/mail/mlhlp1030/mac
• https://www.migrateemails.com/blog/export-office-365-to-mbox/

Replicating “The Feed” feature

HEY Mail comes with The Feed, where you can read newsletters. The problem with The Feed is that it never improved since the original launch of HEYT Mail. The reading experience is nothing special. You can’t compare The Feed to any read-later service. Instead, I diverted all my newsletter subscriptions to the excellent Inoreader service. Now, I’m reading my newsletter in a genuine feed reader through an RSS feed. Problem solved.

Replicating “The Screener” functionality

For some context, the HEY Mail Screener feature allows for triaging incoming emails. Those I don’t want to keep are rejected now and in the future. Anything else will be accepted. The idea is to mark incoming emails from unknown sources to be screened. I use labels and a contact group to replace the screener functionality in HEY Mail. Let’s say you receive an email from “noreply@apple.com” for the first time. It is labelled as “Screener” using the email rule: assign the Screener label if an email is not part of that contacts group. When reviewing those emails, I add the email source address to a contact group called “Well-known Sources” and remove the “Screener” label.

Replicating the Paper Trail functionality

Replicating the HEY Mail Paper trail feature follows the same principles as the Screener feature. A contact group called “Paper Trail” contains all the email source addresses for which I want to assign a label called “Paper Trail”. A mail rule is then required to process all incoming emails by following this logic: any email from a contact who is a member of the “Paper Trail” contact group is assigned the “Paper Trail” label. This is what the following screenshot shows.

From Bubble Up to Snooze

What appears to be novel features in HEY Mail can easily be replaced by something else in Fastmail. The HEY Mail bubble-up feature might have a fancy name but in fact, it’s the equivalent of Fastmail snooze action. If you want to see an email popup the next day, just hit snooze and select the right configuration options. Simple.

A few things left behind

I didn’t migrate everything during this migration process. As I said earlier, I didn’t migrate my calendar. My HEY Mail Contacts were migrated a bit by accident. They were first exported from HEY Mail into an 18 MB file; when I tried to import them into Fastmail, I was expecting a screen to confirm the process and maybe get a chance to set up a contact group for them, which I didn’t get. As a reminder, that contact list was automatically built by HEY Mail over time using the screener feature each time I accepted or rejected an email source. The nice thing about this import, though, is when I select a contact, I get a list of all the related emails from my imported archive. That’s super handy.

HEY Mail Clips weren’t migrated. Those clips were created while reading newsletters. They are lovely in theory, but they serve little purpose once made. They can’t be exported in Markdown, for example. These information tidbits now live in Inoreader, where I spend most of my reading time. This feature has never been updated since its inception, which I find deplorable. Companies quickly add stuff, but improving on them later is often another matter.

Another thing that is left behind is HEY Mail Collections. These were created to group related emails together. I rarely used that functionality; it won’t be missed, but I liked how they were presented, as shown below.

The last thing left behind is HEY Mail workflows. I experimented with this feature for a while to process subscription notification emails coming off Gumroad. A workflow allows for assigning a state to an email. That state can change to reflect a status. Think of this as a Kanban board, but for emails. Workflows was a good start but lacked some essential capabilities that are really useful for my needs. Leaving this behind won’t cause any significant issues.

Some extra Fastmail goodies

Beyond using Fastmail as a unified mailbox, some other goodies come with the service. File-sharing is one of them. A Fastmail subscription comes with a 10 GB storage quota to start. When sharing photos, I can share them as a simple but cute mini website. I can create mini websites tied to a specific folder in your Fastmail files storage. Try visiting an example I put together here. This could become handy and even replace Dropshare, which uses a different backend storage service. Fastmail even provides visitor logs. This is something to think about.

Unexpected but positive consequences

Just like moving from one password manager to another, moving from one email provider to another is the right time to do some cleanup and revisit some strategies. During this migration process, I closed many unused services. I chose to delete my Yahoo account, too. That one was a special use case. My Yahoo account was used to authenticate to my Flickr account, which I decided to close, too. It didn’t have content anyway. This digital cleanup is very satisfying.

The migration was the occasion to remember that an email account is often closely tied to an authentication account. One such example is my Google account or my iCloud account. Both are tied to an email. Unsurprisingly, if you open an account on a web service that offers to sign in with Google or Apple, the associated email will be used to communicate with you by email. My Google account is an authentication account, but I need to link it to my Fastmail account to receive things like YouTube notifications for my YouTube channel. Because I’m a YouTube subscriber, I cannot close my Google account. But again, this was not the main goal for moving to Fastmail.

Some online services I’m using were configured to use my HEY Mail address, which made my migration a bit more challenging for a few services. Some of those accounts were no longer used, so I decided to close them. However, I replaced my account with Fastmail for services like Synology alerting. Not all services use the same workflow for changing the primary email used for authenticating. Some services even make it especially hard. The worst cases are Slack and Bloomberg, which gave me another reason to hate these services as if I didn’t have enough.

Searching for emails is fast and flexible. It’s so much better than anything HEY Mail ever provided. The web interface is clean, adaptable and quick to interact with.

One last thing: Fastmail doesn’t provide a native Mac client. I’m still considering my options. The web client is so good that I can use it instead of a native Mac app. For now, I’m using the web app, which works great. Time will tell.

Am I going to miss HEY Mail?

The short answer is no. While HEY Mail offers a client for all platforms, they are built on the Electron framework and lack basic OS features support like iOS rich notifications. After five years, HEY Mail developers never bothered adding support for these, which allows a user to hit reply right from the notification, which Fastmail supports. HEY Calendar came out last year, and it never really clicked with me. If you think HEY Mail is opinionated, wait until you use HEY Calendar. Again, my primary use case for HEY Mail was for the unified mailbox, so I prefer to keep my calendaring stuff on iCloud. HEY World was a unique HEY Mail proposition: to be able to blog effortlessly. I did use it for a while but eventually decided to move to something more powerful, as I wrote back in 2021. Finally, the one thing that I will really miss is the widgets on the iPhone: they were useful and well-designed for the iPhone as well as for the iPad and the Mac. Fastmail doesn’t support this iOS feature, which is sad. 😔

Concluding remarks

My journey with HEY Mail lasted nearly five years. My subscription will end this coming October. Until then, I'll monitor my HEY mail account to ensure everything is fine. HEY Mail was great when it first started, but it was becoming too hard for me to support the guys behind the service with my hard-earned money. It's called “voting with your money.” I'm done with them; they probably don’t care, and anyone working at 37Signals will never read this article. That's fine. But if anyone ever reads this, please tell your bosses to f∗ off. Thank you. One last thing: Fastmail is cheaper, faster and much more capable.

Finally, I wasn’t paid by Fastmail for writing and sharing this article, but if you are considering joining Fastmail, please do it using this referral link. I'll earn a few dollars. Thank you. If you find this helpful article, please consider supporting me and show your appreciation via my Ko-fi page!