Email Clients

I’m a happy Gmail user, but my university email address cannot be accessed from Gmail (I cannot create an application specific password and Gmail does not support OAuth2). I found the browser UI for Outlook frustrating, so I went in search of another email client.

I looked at and tried a wide range of clients. Below are my notes about what I liked / did not like about each one. Of course, these reflect my preferences. The apps have other features and flaws that were not as important to me (but might be to you).

iPhone Apps

Immediate disqualifying factors:

• Did not support an Office365 account with Oauth2: Gmail, Hey, Superhuman
• I had issues connecting to Office365: PolyMail, Unibox, Zoho
• No snoozing: Apple Mail
• Don’t like the approach to email (group by sender or make it look like chat): Spike, Unibox
• Too expensive: Missive, PolyMail

For those that remained, there are tradeoffs. The table below show factors I considered (more significant factors in bold). One common issue was the way conversations were displayed. The screenshots show how each app displays a new conversation with three unread messages when the conversation is opened for the first time.

App	Positive	Negative	Conversation Screenshot
Airmail	- Can show the entire subject of an email in the message list. - 4+ swipe actions. - Remind if no response.	- Does not open all new messages in a conversation. - Opening previous messages in a conversation inline involves tapping a little arrow (tapping elsewhere opens the email on its own in a new view).
Bluemail		- Does not open all new messages in a conversation. - Swipe actions require a tap as well. - No large templates.
Canary Mail	- Great privacy and security. - Minimise a draft message.	- Does not open all new messages in a conversation. - Once a conversation thread is expanded there is no way to contract it again.
Edison Mail	- Four swipe actions. - Template messages with to-be-filled slots.	- Conversations require opening each message separately.. - Reads email to inform trading (opt-out exists, but its unclear how it interacts with the privacy policy). - Didn’t import my email correctly.
Newton	- Four swipe actions. - Remind if no response.	- Adjusting font size only changes the sender, not the subject of the email. - Does not load all of the conversation, even if the whole thing is new, requiring a tap and waiting. - Does not have a sideways view.
Outlook	- Appears to ensure a minimum font size in messages. - Nice availability sharing. - Select a set of messages and delete / archive them all.	- No template messages.
Spark	- Template messages with pre-filled or to-be-filled slots. - Four swipe actions. - Remind if no response. - Minimise a draft message.
TwoBird	- Notes integrated with email. - Select a set of messages and delete / archive them all.	- Only one swipe action. - No template messages. - Does not have a sideways view.
TypeApp		- Does not open all new messages in a conversation. - Swipe actions require a tap as well. - No large templates.

There is also variation in the message list view, but it is less significant (note, these screenshots are all after I modified the settings for each app to suit my preferences):

Desktop App

Common issues:

• Did not support an Office365 account with Oauth2: Airmail (got it to work in April, but not in September), Boxy, Geary, Gmail, Hey, Kiwi, MailPlane, Mailtab, Mimestream, Postbox, Superhuman
• I had issues connecting to Office365: Zoho, Loop
• Don’t like the approach / more for team email management: Mail Pilot, MailMate, Shift, Spike, Unibox, Front, Helpwise
• Too expensive: Loop, Mailspring, Missive, PolyMail
• Does not support any / enough gmail shortcuts: Apple Mail, Bluemail, Hiri, MailTrim, Outlook (desktop app), Thunderbird, TwoBird, TypeApp
• Doesn’t have a way to show the message list with one line per message: Spark, Canary Mail, Airmail (only has it as a legacy theme with font that is too small for me)

Originally, the list above immediately disqualified those options. However, after 5 months of use, I have discovered a feature that is so critical I will give up other requirements: reminding me if a message has not received a reply. There is an extension for Outlook that provides this, but it costs $15 / month (Boomerang).

My notes on the remaining apps are below, with three groups: (1) top contenders, (2) have some sort of irritating property, (3) have a problem that immediately rules them out for me.

App	Positive	Negative
Mailspring	- Remind if no response. - Can show messages as a list with one line per message. - Gmail shortcuts. - Entire interface scales nicely to have bigger text. - Clean UI. - Template messages with to-be-filled slots. - Swipe actions.	-Syncing issues - Expensive ($96 / year).
Newton	- Remind if no response. - Can show messages as a list with one line per message. - Gmail shortcuts. - Entire interface scales nicely to have bigger text. - Clean UI. - Templates.	- When moving up/down in the message list, if you go off the screen it doesn’t scroll.
Missive	- Remind if no response. - Gmail shortcuts. - Swipe actions. - Has an option for larger text.	- Expensive. - Doesn’t have a way to show the message list with one line per message.
Polymail	- Remind if no response. - Gmail shortcuts. - Swipe actions. - Template messages with to-be-filled slots. - Entire interface scales nicely to have bigger text.	- Expensive. - Doesn’t have a way to show the message list with one line per message.
Outlook (web)	- Can show messages as a list with one line per message. - Gmail shortcuts. - Templates. - Create a quick poll, including one for meeting scheduling. - Entire interface scales nicely to have bigger text.	- Does not support ‘x’ to select messages in the inbox. - Can only snooze messages in the inbox.
eM Client	- Remind if no response. - Can show messages as a list with one line per message. - Can customise shortcuts to match gmail. - Nice control of font sizes. - Clean UI.	- Repeats content in conversations rather than cutting off each message.
Spark	- Remind if no response. - Gmail shortcuts. - Template messages with pre-filled or to-be-filled slots. - Swipe actions.	- Cannot increase the font size of the app (help pages simply tells you to rescale your entire desktop). - Doesn’t have a way to show the message list with one line per message.
Edison Mail	- Can show messages as a list with one line per message. - Gmail shortcuts. - Template messages with to-be-filled slots. - Has an option for larger text. - Clean UI.	- No snooze on desktop. - Reads email to inform trading (opt-out exists, but its unclear how it interacts with the privacy policy).

Conclusion

Original (April 2022):

After all this exploration, I plan to use the Outlook phone app and Outlook web app - not the outcome I expected! I still find the Outlook web app frustrating at times (e.g., if you create a folder it cannot be made a favourite without reloading the page), but by carefully going through the settings I was able to resolve many of the things that originally frustrated me.

It’s slightly disappointing as the other apps did have many neat features that I can see myself using. At some point I’ll revisit Airmail, Canary Mail, Edison Mail, Newton, Spark, and TwoBird.

Update (September 2022):

As noted above, the ability to remind me if a message does not receive a response is an extremely valuable feature that Outlook does not have. This has led me to re-evaluate my options. I am now trying Mailspring.

Update (November and December 2022):

After a few experiences of syncing issues with Mailspring, I am back to the Outlook web app. The specific issues were: (1) sending email and finding hours later that it hadn’t sent, (2) having new email not show up, and (3) moving email to a different folder and not having the change sync back to Outlook.

I have also started using SaneBox, which provides a ‘Reminders’ features that covers the ‘remind if there is no response’ need. It works by forwarding an email (or bcc’ing) a special SaneBox address, like “tomorrow@sanebox.com”, which will then remind you if no one has responded to the email by that time. It is not as convenient as a built-in UI element, but it works, and costs $24 / year (less for educational accounts).

Bonus: Calendar Apps

I initially used Google Calendar and was able to add Outlook to it, but I found that syncing was very slow.

This time I did a more limited search for alternatives, looking at advice online and tried out Fantastical, Any.do, and Calendars. I quickly ruled out Any.do as it visualises the calendar as a list, rather than a layout that shows the time length of events and gaps between them. Calendars and Fantastical both looked good and had fairly similar features. The tie breaker for me was that Fantastical on desktop allows you to click and drag in the calendar view to start defining a new event (Calendars does not).