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Some Thoughts on Migrating Email

/ 4 min read

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I don’t know all the details but the Fastmail Union posted this yesterday:

Obviously - that isn’t a good look. Any layoffs are sad and disappointing but when its 60% of the bargaining unit and all of the committee - it’s definitely a choice. Because of that, I’ve seen a number of good people migrating or making different choices (I’m including links to Mastodon posts in case Fastmail looks at this and sees the consequences of their choices - if you want your link removed, let me know!).

Email migration tends to be a tricky endeavor; it’s a somewhat dated tech that has gotten significantly more ingrained into daily life then I think it was ever intended to. I’ve done two major migrations:

  1. gmail to Fastmail
  2. fastmail to iCloud+

I thought I’d share my process in brief in case it’s helpful to someone. Note up front though: It’s been awhile since I did these so there might be better options available now. Also to note: I’d recommend doing this on a laptop rather than on a mobile device.

Gmail to Fastmail

This was the more difficult one to transition. It took some planning because gmail has IMAP but doesn’t necessarily function as a traditional IMAP account.

  1. I started with some pre-work: labeling the most important senders with a label denoting such. This was straightforward because I was already doing some filtering on messages.
  2. The next step involved making sure Fastmail was all setup. At this point, I was moving to a new domain and verified it was all working.
  3. I then added both accounts to a local client, Mailmate. It doesn’t look like much but it’s super powerful and has been my main email client for a long time.
  4. In the Fastmail account, I created new mailbox (or folder - language might vary with your client) named something like “backup”.
  5. I then dragged and dropped the messages in the label folders in the Gmail account into this new mailbox in the Fastmail account.
  6. Once this finished (and it could take awhile depending on the size of the label folders) I unattached the gmail account from my client and logged into the web interface to finalize things.
  7. In the Gmail web interface I did two things (that are optional): I set an automatic forward for non-junk mail to go to my new account and I also set an autoresponder which I left on for about 3 months.

Gmail doesn’t seem to be going away so I’ve left the forward on. Very rarely (maybe two or three times in the last 7 years?) I’ve logged in to look for an old message that didn’t make it over. And there was one client for work that would only accept messages from gmail or googleapps so I had to login and send from the web to communicate with them (don’t ask me why, I could never figure that one out). Other than that though it doesn’t get use outside of the occasional oauth app.

Fastmail to iCloud+

In the summer of 2022 I realized that 1) Apple One family made sense for us and 2) iCloud+ that came with it included the ability to use a domain. It then made sense to move off of Fastmail and save that service fee to use what we were paying for anyways.

The process for this move in some ways was easier and in other ways trickier (because a domain was involved). Here’s how I did it:

  1. I backed up the domain zone file and then I got the domain setup in iCloud+.
  2. Once I verified that it was working, I logged it into Mailmate along side Fastmail.
  3. I let these two “work” side by side for about 48 hrs until I stopped receiving messages into Fastmail. It took about that long because of DNS propagation and I wanted to make sure everything was fully switched over to iCloud+ before moving messages.
  4. I made new mailbox(s) in the iCloud+ account to mirror the Fastmail setup and then dragged all the messages from Fastmail into iCloud+.
  5. Once it finished (it took awhile), I removed the Fastmail account from Mailmate and logged into the web interface for it.
  6. Here, I went into my admin settings and downloaded mailbox backups as a precautionary matter. Today, I believe this is under “Migration” -> “Export” -> “Mail Export” but could be wrong on that.
  7. After this, the only thing left was to close the account.

Hopefully that all made sense. And hopefully it’s helpful if you are looking to make an email change anytime soon. Sometimes, it’s nice to even just see or hear others processes to develop your own!

Have a thought? Or comment? Reply on Mastodon!