Why I’m Migrating from Google Workspace and Outlook to iCloud+

Google Workspace

My Google Workspace subscription is becoming increasingly more expensive 💰. The current price is £8.28 for the Business Standard plan, and next month this will be increasing to £9.20. This has become too expensive for me, and I’ve been looking for a cheaper alternative.

Outlook Mail

I have an Outlook account which has been lying dormant for a long time now.

Come on, don’t judge me! We all have that one email account that we don’t use anymore… right?! 😅 🥵

Anyways… This account has lots of old emails that I’d like to keep for archival purposes. Whilst migrating my Google Workspace account to iCloud+, I’d like to migrate these old emails too.

iCloud+

I’m already in the Apple ecosystem, and I recently purchased iCloud+ for £0.99 per month. This provides 50GB of storage which is more than enough for my needs. I also noticed you can use your own domain for email (which was the main reason I was using Google Workspace), and you can add up to 5 custom domains with 3 email addresses each! So I’ve decided to migrate my emails to iCloud+ to save money and simplify my setup.

I’d like to begin by thanking Myles Gray for his excellent blog post on his experience migrating from Google Workspace to iCloud+. I used this as a guide for my migration.

Migrating Emails

Similar to Myles, I used imapsync to migrate my emails to iCloud+. imapsync is a well established and battle tested tool for migrating emails using the IMAP protocol. Being actively maintained, free and open-source, with lots of documentation and examples, it seemed like the perfect tool for the job. I used the imapsync container image to migrate my emails. I’m now sponsoring the maintainer on GitHub too! :slight_smile:

Before getting started you must have done the following:

The app specific passwords are needed if your account has two-factor authentication enabled (It’s 2023 people! You should have this enabled! 😅)

Migrating Google Workspace Emails to iCloud Mail

Initially, I used the command below to migrate my emails from Google Workspace to iCloud Mail:

docker run gilleslamiral/imapsync imapsync --errorsmax 200 --user1 <Gmail Address> --password1 "<Gmail App Password>" --host2 imap.mail.me.com --ssl2 --user2 <iCloud Address> --password2 "<iCloud+ App Password>" --gmail1

However, once the sync finished I noticed that some of the emails were not in the right folders 😕 What I didn’t realise was that as well as my custom labels (which are just IMAP folders), Gmail also applies an INBOX label to all emails 🙄. The default behaviour of imapsync is:

The first label synced by imapsync goes to its corresponding folder but other labels are then ignored. By default imapsync syncs folders (Gmail labels) using the classical alphanumeric order.

imapsync Gmail FAQ 1

This is why some of my emails were not in the right folders!

Since I now had emails in the wrong folders, I had to delete them from iCloud Mail and start again 🫠:

docker run gilleslamiral/imapsync imapsync --errorsmax 200 --user1 <iCloud Address> --password1 "<iCloud+ App Password>" --host1 imap.mail.me.com -ssl1 --host2 imap.mail.me.com --ssl2 --user2 <iCloud Address> --password2 "<iCloud+ App Password>" --delete1 --noexpungeaftereach

Now, I ran the sync again but this time using the --folderlast option to sync the INBOX label last:

docker run gilleslamiral/imapsync imapsync --errorsmax 200 --user1 <Gmail Address> --password1 "<Gmail App Password>" --host2 imap.mail.me.com --ssl2 --user2 <iCloud Address> --password2 "<iCloud+ App Password>" --gmail1 --folderlast "INBOX" --folderlast "[Gmail]/All Mail"

In the end, I synced 1109 emails (390.7 MiB) which took 23 minutes and 51 seconds. This was the amount once imapsync skipped cross duplicates (emails labelled multiple times). I relied heavily on the --dry option to test the sync before running it for real.

Migrating Outlook Emails to iCloud Mail

Next, I migrated my Outlook emails to iCloud Mail. As the emails in this account were very old, I wanted to put them all into a single folder called Other/Outlook|Personal. I used the following command to do this:

docker run gilleslamiral/imapsync imapsync --errorsmax 200 --user1 <Outlook Address> --office1 --password1 "<Outlook App Password>" --host2 imap.mail.me.com --ssl2 --user2 <iCloud Address> --password2 "<iCloud+ App Password>" --regextrans2 "s/(.*)/Other\/Outlook|Personal/" --folder "Inbox"

This synced 422 emails which took only a couple of minutes to complete. This sync went a lot smoother than the last one! 😆 😅

Correcting DNS Records

Now that I’d migrated my emails, I needed to update my DNS MX and TXT records to point to iCloud Mail. Returning to iCloud+ and on the Custom Email Domain setup, I completed step 3. I use Cloudflare for DNS and I was pleasantly surprised to find Apple provides integration with Cloudflare to automatically amend my DNS records for me! 😃 I just had to confirm the changes and wait for the changes to propagate.

Conclusion

In the end, I’d successfully migrated 1531 emails from Google Workspace and Outlook to iCloud+, and I’m saving money! 💸 🎉

References

  1. https://imapsync.lamiral.info/FAQ.d/FAQ.Gmail.txt ↩︎