My Email Game (Update)

I love email. It was one of the first things I used when I got online back in 2000, and it's still here. It just works.

But a lot in email gets me headaches and that is always mail client specific, like:

  • Interrupted threads when someone started a new subject to discuss a previous topic, and the inability of mail clients to add a mail to an existing thread.
  • HTML email is a pain in the rear and even worse is the garbage that every HTML mail editor adds (I'm looking at you Microsoft Office/Outlook however you call yourself these days)
  • Email clients that can't read my mind what's important and what not (classify emails).
  • No native markdown to HTML converter (given if you use basic Markdown formatting in text-only emails, the client might render it bold or italic, but no headlines or anything).
  • Adding notes to email (without sending mails to myself, but I guess that's the way to do)

So far, my journey included the following email clients:

  • Outlook Express did its thin, butt once I tried Eudora, there was no going back unless I had to.
  • With the demise of Eudora I tried BAT! mail, an incredible powerful and ugly mail client and Pegasus Mail - I can't remember it wasn't good.
  • Mozilla Thunderbird entered the scene and everything was possible. Extensions for every use case and active development.
  • I used Thunderbird exclusively and over time I missed some features like the two row mail listing, that was never planned to change and other features were just hacky (thread view)
  • Postbox claimed to solve my problems and it was based on Thunderbird, so it was compatible with Thunderbird formats and it looked fresh. The first time I spend money on a mail client.
  • Sometimes I opened Gmail but never got used to it, until Googles Experiment Mailbox came on the scene. That was fantastic. Especially the classification of mails helped to deal with large amout of mail and promo mails.
  • Webinterfaces never felt right, Mailbox was shut down, Gmail sucks, Postbox was still there, but facing a difficult decision, because Thunderbird was about to be rebuild and only supporting their new webextensions.
  • Postbox closed their interface to use extensions, so a whole world of functionality I got used to disappear. "Send later", "Snooze Email" and the "Markdown Here" extension. Big bummer, but I kept using Postbox because I paid for it and it was still nice.
  • Today Postbox allows extensions again, but there are no compatible Thunderbird extensions anymore and no one cares about making them compatible. Not even Postbox. Markdown-Here got an update by the community, and it barely works. New features appear in Postbox sporadically, but nothing earth-shattering. Instead, they try to sell themes. Who cares?
  • I gave eM Client and Mailbird a shot. Mailbird is some garbage subscription Electron app. No thanks. eM Client impressed me mildly but suddenly I miss some Postbox features (RSS, complex filter, inline reply) I got used to and it wants another 50 to 70 EUR for a license.
  • Update 2023-07-29: I'm using my Office 365 address with Outlook Web. I have to say, it's working well so far. I even setup the native Microsoft Mail (I just wanted to connect my calendar) and it's not too bad either for just email.
  • For Bulk Email I started to use Betterbird, a Thunderbird fork with some fixes and some things that make it better, according to the developer. I can't tell what it is, but it's definitely not the UI/layout of the app.
  • Thunderbird announced to overhaul their ancient mail client and with Thunderbird Supernova they delivered the first version of their modernized email client. It has a multiline message list, and that sold it to me. I'm in the process of finally leaving Postbox and enjoying the integration of LanguageTool, Mailmerge, Markdown-Here.

eM Client as alternative?

eM Client has a working calender and address book. Postbox had Lightning in the past, but they got rid of it. I used the Sunlight calendar for a while but it got bought by Microsoft and then was shut down. The Microsoft calendar is not bad, but it's unreliable with WebDav calendar on Nextcloud.

eM Client impressed me with their thoughtful features, like showing a history of mails from the sender in an active mail, build in calendar and addressbook, notes and even chat (uses some chat protocols that I don't use, so there is that).

Now, the HTML editor in eM Client is just a basic textfield. They didn't even bother to use a monotype font. So it's hard to create html mail in there or signatures. It has wysiwyg tools though, but I don't trust them.

A thing I always ignored in email is encryption. I think the fact that no normal person is able to understand and setup PGP keys left this feature unused by 98% of mail users.

I've never received an encrypted email.

eM Client seems to make the setup easy, but I believe if nobody is using, why bother.

The filter capabilities in eM Client seem to be inferior to Postbox/Thunderbird. No time based filter (delete messages older than x days).

Another downside and a show stopper is the absence of an update of the "unread Mails" count on IMAP subfolders, according to this forum post: No updates or notifications from subfolders? - #55 by curious - Mail - eM Client. That's bad and I guess won't make me using it.

Other alternatives?

I can think of two: Hey Mail from the creators of Basecamp. It's a paid browser based client that seems to become very popular and I guess you have to use their mail address.

And there is Plum Mail which looks like a web client with some nice helpers, to pin mails and make notes and keep a conversation together. Subscription based and in beta right now. So I'll pass again.

Email tools I use or wish that existed

1. Classification of mails

Every mail client has a trainable spam filter. You would think that this technology could be implemented to train the algo to classify other topics? Nope. Nowhere to find in offline mail clients. That's only offered by cloud based mail systems like Gmail, Hey etc.

But there is Popfile - it's an ancient piece of software, last updated 2015 that sits between your mail client and the mailserver and analyzes mails and sort it into folders. It comes with a webinterface to train your mail and just works fine. Only thing to criticize is it works with only one IMAP connection. That's a bummer, but for my main mailbox it kind of works well to differenciate between notification mail, spam and important stuff.

2. Merging loose mail threads

There was a Thunderbird extension that aimed to do that, but as far as I know, mail threads are identified by a message-id and I think it's up to the mail client to be lax and group by subject line or whatever. Oh well.

3. Markdown

It seems like such a niche feature that probably is easy to implement (especially for Postbox, since there is an existing extension they just need to fix), but so far there is only one MacOS client that offers Markdown out of the box, so I won't hold my breath that eM Client or any other client will see that feature ever. (There is Markdown-Here Revival which works nicely)

4. Procmail filter editor in client

If I setup a local email filter I would love to see that reflected optionally as procmail filter on the server. But I guess that's too special and works only if your provider gives you access or an interface to that (as does) combined with a Bayes filter like Popfile - that would be perfect.

5. Exchange support

I have to use at least one Exchange mail account and I don't want to know too much about this weird Microsoft product, just so much, it is not easy to setup if you don't use Outlook or some other MS software, especially if an ancient version of Exchange is used. I have to run a little proxy called DavMail that sits between Postbox or eM Client and deals with Exchange server. Works alright, but y tho?

Update: with Office 365 it's better integrated, until they changed something with their IMAP/SMTP connections. Either I use Outlook Web or in Thunderbid I now have to use this Owl extension because Thunderbird or MS messes up Unicode characters and umlauts when sending via SMTP. (Ä turns to ?). Y tho?

Encrypted chat via email

A well setup mail client is one thing, but what if you could use email as chat app? There is the Delta Chat messenger app, that connects to your email account, and offers you a nice chat interface as you know it from Signal or WhatsApp or Skype. Messages are simple emails that your chat partner can read in their email client. And if they use Delta Chat as well, it's even better. And if both partys youse Delta Chat, then they can use the Autoencrypt feature so messages are only readable by the client and nowhere else.

This is a really privacy friendly way to use a proven, robust and decentral infrastructure to communicate.

As far as I understand, this is not as secure messaging as Signal, because email metadata is not encrypted and therefore you leave traces. But I'm no expert here, I just think Delta Chat is a good thing to have.

tl;tr or conclusion

There isn't one. I guess I keep working around the pain I have with Postbox and won't inflict pain in buying eM Client at this point and work around other issues there switch back to Thunderbird, now that they have multiline message list (or cards as they call it).

As Chris Coyier states:

In fact, you come to love [email], because of how effective of a communication method it is: it’s public, it’s async, it can hold files, it can be of any length, it’s threaded.

Tooling isn’t needed to “fix” email. Email clients these days, for the most part, are interchangeably good.

Not a Big Deal – Email is Good