From Outlook to ProtonMail 🟪

Recently, our family made the switch from using Microsoft Outlook to ProtonMail for our email needs, and so far, it’s been a positive experience. Here’s a look at why we made the change, how the transition went, and what we think of ProtonMail compared to Outlook.

Why We Left Outlook

For years, Microsoft allowed custom domain names with Outlook if you had an Office 365 Family subscription. Since everyone in our family uses Office, it was a natural choice to unify our email under Outlook and take advantage of the Office suite. It worked well for a long time, even though integrating custom domains with some third party email clients could be a bit tricky at first. Over time, those issues smoothed out, and we rarely had problems.

However things changed when Microsoft announced they would discontinue support for custom domains on family plans. The real tipping point came when my sister noticed her emails were landing in spam folders. After a quick check, I realized our DKIM records weren’t set up properly, which meant our email configuration wasn’t optimal. When I tried to fix it, I discovered Microsoft had also disabled the ability to update custom domain settings, essentially forcing us to look for alternatives.

Exploring Alternatives

My dad and I, being the more tech-savvy members of the family, started researching privacy-focused email providers. We considered several options:

• ProtonMail: Well-known for its strong privacy and security features. Based (currently) in Switzerland which seemed like a pro.
• Tuta: Similar to ProtonMail, but less familiar to us.
• HushMail: Didn’t quite fit our needs.
• Fastmail: I’ve used it for other domains and found it reliable, especially after they acquired PO Box, a service I liked for email forwarding.

After weighing the pros and cons, we chose ProtonMail. It felt like the best long-term solution for privacy, as their encryption means even ProtonMail can’t read our emails once they’re encrypted. While there are some technical asterisks (like that email is not actually received encrypted, but rather encrypted before stored), for our family’s needs, ProtonMail’s privacy is more than sufficient.

The Transition Process

We signed up for the Proton Family plan, which comes with a lot of features—maybe even too many! Besides email, you get:

• Proton Calendar: A solid replacement for our previous calendar setup in Outlook. Although not shareable to e.g. Google Calendar, which I am using right now to manage multiple calendars.
• Proton Drive: Could eventually replace OneDrive for us, though we’re still using Microsoft Office for now, no we'll have access to both.
• Proton VPN: A good introduction to VPNs for my parents, who only have used VPNs before mainly for streaming while abroad.
• Proton Pass: A password manager that my dad has started using (I think/hope).
• Proton Wallet: A crypto wallet, which I don't really see the point of them including.

As a developer, I found the DNS setup straightforward, and ProtonMail handled the email migration smoothly. Importing emails from Outlook took a while for my mom and sister, who had a lot of messages, but everything worked out in the end.

Life with ProtonMail

We’re now paying a bit more than before, but it feels worth it to me. The ProtonMail client is smooth and user-friendly on both iOS and Mac, and I haven’t heard any complaints from the rest of the family. It has all the features we need, and the interface is clean and organized. I especially appreciate the cleanliness of folders and labels in the desktop/web client.

ProtonMail even offers an AI writing assistant, which I tried once with decent results (though it struggled a bit with Swedish). Overall, the interface feels cleaner than Outlook, even if it has a few quirks.

Why We Chose Microsoft Outlook in the First Place

Originally, we picked Outlook because we wanted to unify our digital lives: one place for files (OneDrive), email with our custom domain (Outlook), and access to the Office suite. It made sense at the time, but as Microsoft’s policies changed, we needed a new solution. Also privacy concerns are increasing as AI trains on content hosted by these big cloud providers, making it questionable as to how private our files really are.

Final Thoughts

Switching to ProtonMail has been a smooth experience for our family. We (or at least I) feel more secure knowing our emails are private, and the extra features are a nice bonus. While we’re still using some Microsoft services, and probably will continue to for a while, the migration to ProtonMail should be considered a success!