Email provider notes and comparison

Overview

This is a pretty cluttered collection of notes and observations I made while testing various email providers as potential replacements for our Google Workspace family account. See my main article on Google Workspace alternatives for families for more context.

The analysis is not really complete, as we decided to go with Fastmail and are pretty happy with it. Still, I wanted to share my notes for anyone interested. So, seeing a lot of “?” in the table below means: I did not test this feature or aspect in detail.

I tried to keep this as objective as possible, but of course, some subjective opinions will sneak in here and there.

Calendar

• Fastmail invites cannot be displayed in Proton
• Tutanota RSVPs are not understood by Google

Email

Deliverability

My first Zoho mails landed directly in Spam. There was one message from ProtonMail that Gmail marked as “might be fishing” (but still delivered it into the inbox). Both issues were resolved, by manually marking those mails as not spam/not scary.

Folder handling

• Fastmail allows switching between labels and folders at any time (for each user individually)
• Tutanota does not support previewing email attachments
• ProtonMail uses folders AND labels.

UI

Overall appeal

Ok, this is going to be very subjective. I try to express how much I like the design and UX of a certain user interface. My rating here changed during the test adn generally speaking you can say: The more refined an interface looks and feels, the more stars it get, the more cluttered or buggy it is, the more stars will taken away again.

Keyboard support

Some providers (… Tutanota) will have minimal support for navigating the interface with the cursor keys. If there’s no support for basic email management functionality, this will not count as keyboard support.

“One-click triaging”

Being able to archive or delete individual mail in list view with one key or a single button.

“Walkthrough mode”

Being able to walk through the conversions/mails in the inbox without going back to detail mode or manually finding and selecting the next mail. This usually comes naturally with a three-pane layout and is typically implemented with keyboard commands and/or specific links on top of the mail (“next/previous conversation”).

	Google Workspace	Fastmail	ProtonMail	Mailbox.org	Zoho Mail	Tutanota
Webmail User Interface
Overall appeal	★★☆☆☆	★★★★★	★★★★☆	★★☆☆☆	★★☆☆☆	★☆☆☆☆
Folders or labels	labels	users can switch any time	both	folders (+ colors)	both	folders
Layout	2/3-pane	2/3-pane	3/2-pane	3-pane	2&3-pane	3-pane
Mailbox view	threaded/list	threaded/list	threaded/list	threaded/list	threaded/list	list
Keyboard support	✔️	✔️	✔️	—	✔️	—
One-click triaging	✔️	✔️	✔️	✔️	✔️	—
Walkthrough mode	✔️*	✔️*	✔️*	✔️	✔️	✔️
Message flagging	✔️ (“star”)	✔️* (“pin“)	✔️ (“star”)	—* (“star”)	✔️ (“flag”)	—
Snooze mode	✔️	✔️	—	—	✔️	✔️
Composing in detached/overlay window?	✔️	—	?	?	?	?
Allows attaching files via DnD	✔️	?	✔️	✔️	?	?
Allows attaching images via DnD	—	?	✔️	✔️	?	?
Allows adding images inline via DnD	✔️	?	✔️	✔️	?	?
Security
Session management	✔️	✔️	✔️	✔️	✔️	✔️
Encryption at rest	✔️(src)	✔️(src)	?(src)	—(src)	✔️(src)	?
Per-user encryption of message content at rest	—	—(src)	✔️(src)	—(src)*	—	✔️(src)
Client-side encryption	—	—	✔️(src)	—	—	TBD: ✔️(src)
Zero-knowledge encryption	—	—	✔️(src)	—	—	?
Transparency
Open protocols	—/✔️	✔️	?	?	✔️	?
Open Source client(s)	—	—	✔️(src)	—(src)	—	✔️(src)
Public Roadmap	?	?	—(src)	—(src)	?	✔️(src)
Transparency reports	?	?	✔️(src)	✔️(src)	?	✔️(src)

Bugs & random observations

• Layout: The default layout of ProtonMail is a pretty nice, keyboard-walkable 3-pane layout. Alas, sometimes the keyboard seems to be stuck or the focus is lost and the user has to resort to click a message in the list to get it working again.

  Zoho Mail has no traditional 2-pane or 3-pane mode, but a view that starts in 2-pane mode and switches to a 3-pane layout as soon as a mail is opened. While there are many options how to show a messages details (separate tab, separate window, horizontal or vertical split), there’s no way to configure a 2-pane mode where the list is hidden, while a message is being looked at.

• One-click triaging: Gmail has a set of action buttons (archive, delete, mark read, snooze) that show up when hovering a message in the list: Cool. Sometimes, when deleting mails, the next mail will show up at the same spot, but the hover buttons will not, so by clicking again to delete this message, you’re acually opening it. Makes me livid.

• Walkthrough mode: For Google, Fastmail, and ProtonMail walkthrough mode will not really work for managing lots of mails, as triggering an action for a specific mail will close the detail view instead of opening the next mail in the list. For Google and Fastmail this can be circumvented by switching to the 3-pane layout, for ProtonMail it will happen in 2-pane and 3-pane layout.

• Message flagging: Why is there no default filter for showing all “pinned” messages in Fastmail? It can easily be set up, though. In Mailbox.org, you cannot search for or filter starred messages. Tutanota does not support flagging messages at all.

• Per-user encryption of stored message content: For Mailbox.org, there’s a optional feature called “The Encrypted Mailbox” which supposedly allows manually encrypting your message contents using a server-stored PGP key. I did not try this.

• I came to like the contextual sidebar in Fastmail.

• I cannot stress enough, how ridiculous the way Zoho Mail is scattered across different domains names is. Every time I tried logging into the web interface I needed multiple attempts. If you’d ask me now, what the offical URL for checking your email as a Zoho customer is, I still could not answer this. (Ok, I tried again, and the best possible URL for my account seems to be https://accounts.zoho.eu/signin?serviceurl=https://mail.zoho.eu – no kidding)

Fastmail-specific migration notes

• Disable holiday and birthday calendars in Gmail before attempting to copy them over.
• Fastmail configuration settings: https://www.fastmail.help/hc/en-us/articles/1500000278342-Server-names-and-ports
• Fastmail forces you to use App Passwords. AWESOME.
• Fastmail: ~5 minutes for 1000 contacts and ~1000 events, 37 minutes for ~42k mails
• Fastmail: Correct handling of walk-through mode can be enabled in extended settings, YAY.
• Fastmail: Handling of calendar events (auto add to calendar and archive) can be enabled in settings