Gmail to ProtonMail to iCloud Mail

My email account journey: Free to Freemium to Premium

I went from using a free product with no data privacy (Gmail) to a freemium product with full privacy/security (ProtonMail) to a premium product with full privacy/security/ecosystem (Custom Email Domain on iCloud Mail) Like many others, I am one of the initial Google Mail (Gmail) users, who signed up on Gmail through invite-only access around the year of 2004. As a Gmail user, I was happy with Gmail which gave me a lot of free perks until I realized that free Gmail comes with the toll of privacy & security (Google has access to all my private to confidential or important data).

In December 2015, I purchased a separate domain to privately host and manage my personal communications (email, calendar, etc.) with complete data protection and privacy. After a few days of online research, I decided to purchase the Proton's Mail Plus plan and migrated my emails from Gmail to ProtonMail. I liked using ProtonMail due to data privacy and security, except a few quirks (as of Nov-2022) such as calendar file attachments not working well in Mac/iPhone, and my work network keeps blocking ProtonMail’s Web app from sending emails. Moreover, Proton’s products (Mail, Calendar, etc.) have not been well integrated with the Apple iCloud ecosystem, which I would like to stay within.

In November 2022, I decided to move from ProtonMail to iCloud Mail (Custom Email Domain), which is part of the iCloud+ subscription with no additional cost. Adding an existing domain in Custom Email Domain on iCloud+ including DNS values setup with the domain registrar (mine is Cloudflare) was easy and straightforward. However, migrating existing emails from ProtonMail to iCloud Mail was not easy as there was no option to import emails automatically. I had to create a ticket with Apple support (phone call with them for around 96 minutes) to troubleshoot the issue. Finally, with the guidance of Apple support (a big thanks), I followed the below (manual!!) steps on Mac and successfully migrated (or copied) all my emails from ProtonMail to iCloud Mail:

• Download and install ProtonMail Bridge app for Mac in your Mac, and create a user profile on that Bridge app by sign-in using your ProtonMail user account reference. Outcome: You signed in successfully onto the ProtonMail Bridge app and shows as “Connected” along with the size of the total emails
• Open Mail app on your Mac, go to Accounts page and add ProtonMail Bridge account that you have created in step #1. Outcome: ProtonMail Bridge account shows up in Mac’s Mail app with all emails (including Labels if any created) from ProtonMail
• From your Mac’s Mail app, you will have to manually copy or move all emails separately from each ProtonMail Bridge folder (Inbox, Sent, Draft, Labels, etc.) to corresponding iCloud’s folders (Inbox, Sent, Draft, etc.). Few notes…

  I chose to “copy” (Command-C buttons) and paste (Command-V buttons) emails instead of “move” emails because if something goes wrong during this process I will still have all my emails in ProtonMail account If you have emails under Labels/Folders in ProtonMail and you want to keep the same as organized way in iCloud, you will have to create folder(s) manually first within Labels under iCloud and copy/paste emails manually onto those folders separately from ProtonMail Bridge’s to iCloud’s. This can be very time consuming based on number of Labels/Folders and emails within those that you have

• Just as a clean up, in your domain registrar’s page review the DNS setup and remove any info that related to ProtonMail if you notice

That’s all! You should be all set to send/receive emails from your iCloud Mail within Apple iCloud ecosystem.