ALL THE GOOD EMAIL CLIENTS GO TO HELL

Something's been compelling me lately. Admittedly, I may have a tendency to obsess, but this is really a special case of rubythinking - It all started a few months back, when for some reason, my phone suddenly refused to communicate with my mailserver. My mailserver - vulpecula.uberspace.de - is one of the many that Uberspace hosts. I've talked about them before, and not only are they my hosting provider of choice, they are also the place I trust the most with server maintenance.

The great thing about Uberspace is that they do everything just like you would yourself. Their servers are literally just bog standard linux boxes. They run sendmail, nginx, and a little bespoke utility that lets you configure those without having to delve into config text files. It's quite powerful, and more importantly, this means that everything they do is completely by the books and predictable. Hosting at Uberspace is pretty close to actually hosting yourself. It also means that their mailserver config is more or less exactly as RFC 9051 and its obsolescences want them to be. Ports are what they should be. TLS and SSL is supported, at the correct ports. It's a joy to use.

So imagine my surprise when suddenly, out of nowhere, Apple Mail on iOS refused to communicate with the SMTP server. It could read email fine, most of the time - but sending it was out of the question. It just plopped my emails in the outbox, which I didn't even know the Apple Mail app supported displaying.

I put in a solid afternoon troubleshooting this, but I couldn't figure out what was causing the issue. Uberspace staff, consider this my bug report - and no, I don't have any further information on what happened or why it happens only on iOS and iPadOS. I'm in the dark here. Regardless, this appears to be a client issue anyways; I tried other clients and they all - with some exceptions - worked perfectly. Or, well, not perfectly, but that's not the server's fault.

I went through at least 15 email clients. All of them suck. I'm being completely genuine - I've not found a single email client that works as you'd expect. I've found ones that I can tolerate, but that's about all I can do here really.

Let's run through a few - Outlook, the golden boy. Sure. It's not free, despite what Microsoft wants you to believe, and I use it at my job because we're suffering from the disease known as Exchange there, so I was familiar. The "New Outlook", the one that comes with Windows (someone call the branding police), is just straight up garbage. I connected my accounts, all three, and immediately it informed me that my credentials and emails would be also stored on Microsoft's servers. I don't even know how I'd begin to rationalise that, but cautiously, I pressed on. I was presented by a new email. Great, that works - but wait, that's not an email. It's an ad, made to look like an email in your inbox. Unacceptable. Next.

Outlook 2019, the paid one, was... okay. Nothing special. Way too bloated, took forever to load, and to this day I don't understand why Microsoft insists on essentially having two seperate Outlooks for when connecting to an Exchange server or anything else. I can use Outlook, it's okay, but it's infested with Microsoft's business nonsense. For instance, the "Forward to manager" QuickStep shortcut is baked in to the UI, even though it knows that I'm running the Home and Student version. That's annoying, and to me is just another symptom of Microsoft seemingly being unaware there is life outside an office. I won't go into it here, but Microsoft's concept of reality is almost creepily corporate.

Just for shits and giggles, I also tried Outlook 2010. Quite frankly, I prefer that style of UI, it's charmingly dated. It's also gold, instead of blue. Why they ever changed that is beyond me.

Outlook 2010 needs some convincing to connect to IMAP servers. It can do it, but it defaults to port 143, and doesn't understand that SMTP servers also require authentication these days. You can make it work, but you have to be dedicated. Once inside though, aside from the wallpaper and the furniture, it's just Outlook. Exactly the same. One wonders what Microsoft has been doing in the years between Office 2010 and 2019, but it clearly wasn't improving the email experience. Forward to Manager makes a reappearance here.

Some more grievances about this outdated app nobody should use - it doesn't do IMAP keywords, even if you try and force it to, it doesn't understand threads, doesn't auto-read emails you click on by default, and of course there's the vestigial tail of "Send/Receive All Folders" that evokes HotSync feelings of yesterdecade. But other than that - and to its credit, it does at least try to autosync - it's just Outlook. Don't close it though, it can't run in the background.

Admittedly, that's not where my journey started. I started with Thunderbird, which is more or less what everyone uses. Thunderbitd is... fine? It has a lot of the same issues that Outlook has, and I personally think the interface isn't suited to power users that use IMAP keywords and folders a lot, and even though it offers extensions, they haven't been touched in years. Most of them don't have screenshots and when they do, they're usually with the Windows 2000 UI. Shout out to Eudora, by the way.

There is a certain dichotomy in email clients. As far as I can tell, there's two general design styles - pretentious (this is your Spark, Superhuman, Airmail and so on) and crusty (which is your classic Outlook, Apple Mail, basically every native app). The Bat! for Windows is a special case because it marries those two styles. Yes, it's native. I think. I refuse to check. Yes, it also shows Email like Spark, and in true terrible app fashion, the Reply/All/Forward buttons are round and at the top of the message where they overlap the bounding box - but we won't hold that against The Bat!. Don't be confused by the name, by the way. The name is really the one thing about The Bat! that I can excuse. Because good lord, is this app poorly designed. Every email in the email list has three buttons to the side. Every. Single. One. This clutters up the interface, as does the weirdly centre-aligned toolbar which does not at all gel with the classic three-pane UI of folders, emails, and current message. Add to that that they want you to pay for this software Fiat Multipla, and you see why Outlook and Thunderbird are popular.

On iOS, the offerings are hardly any better. Airmail is DOA, Spark does the NuOutlook thing of having to proxy your emails through their servers (presumably for notifications), Superhuman is 20 quid a month, and of course, every single one of these apps insists on grafting AI junk on top that you need to pay for, but you also need to pay for every other sensible feature like multiple accounts. It's a mess.

There's always an insane option, of course. An option so obviously designed for and by giant nerds that have no idea how to design an app. You know the ones. Your GIMP, your Blender, your VLC. They all suck. Nobody enjoys using them, but they do anyways, because they're free and can do everything, somehow. Preside Mail on iPhone is no different.

First, it's not native. It feels off. Not like an iPhone app should. There's tiny delays everywhere and th visual effects are in the UX equivalent of the uncanny valley. It also refuses to ever let go of a feature - a digital hoarder's home. You can still - admittedly, to my immense delight - turn on the iOS 6-style skeuomorph UI. That's lovely. Everything else isn't though - Preside does email, contacts, calendars, tasks, and it kind of sucks at all of them. It also exposes every single setting you could want. For this, it actually has a "settings level" menu that lets you choose how many settings you want it to show to you. It hands you control over things you should never have control over. It lets you choose what method it uses to update in the background, for Pete's sake. And despite all this, it's not a very good email client. Composing an email is clunky, as is attaching items. Filing and organising is a mess specifically because it brings all the intricacies of IMAP management to the small screen, and that's a labyrinth. I lost my dog in the menus of Preside, and I'm probably not doing to see him ever again. I barely know how to mark an email as read, and by the way, swipe to go back is not supported.

The Mac version of the insane email app is MailMate, by the way. I love it to death - it's also the closest you can get to direct IMAP control, and unlike Preside, it is actually native. It has ridiculous features like "Scramble Mode" which shifts all letters on the screen over randomly in a Caesar cipher so you can take screenshots without exposing your details, it integrates with four dozen different task management apps - including yours - it has a brilliant Thread Arcs feature that visualises email like a Git tree and all of this doesn't matter because it only supports IMAP. Like I said, I love it. But it's not good.

And that doesn't leave very much! I chose to stay with Preside, Outlook 2010 and MailMate because I clearly can't be trusted, but as I hope you've come to realise, dear reader, all of these suck! There are no good Email clients! Not one! Not even by accident! Where did they all go?

I think this has something to do with - of course - the way society has changed. When email was formalised, it was literally that - electronic mail. You sent letters. They had a letterhead and a context, a signature, and sometimes a photo was attached. Not so nowadays. Email is a complex thing now, it can even run JavaScript if you're reckless enough, it can report back through tracking pixels and if you send a marketing email that's not a modern HTML nightmare, you're not going to be taken seriously.

Naturally, this also changed how we perceive our messages. Much like the iPhone changed text messages into bubbles and our perception of the medium to instant messages, email changed as well, but in the other direction. Email is - despite being as fast as IM these days - the slow comms. The snail mail. Esnail email, if you will. Most of your emails don't even get a second thought, because they're advertising. Newsletters. Spam. Nigerian princes in desperate need of an account to transfer all those dollars into. You get so many of them you need to speed through them.

Emails are the only form of modern comms you're likely to batch process. You select a lot of them, mark them as read, then archive them. They're not messages, they're entries. Files. Quantity over quality, in most cases. Which leads to Email clients being designed with this in mind. Most notably: Email clients provide a list of messages, and not a list of people, unlike iMessage or WhatsApp.

The early clients understood this intuitively. Outlook and Eudora, rest in power, were exactly made for this. You didn't even have to leave the email list to look at the message. You filed it away, maybe you replied, and only then was a new window opened. Most modern clients don't do this. Instead, they put the sender front and centre, with a big round picture (something tacked onto the email standard by techbros, by the way) and most modern clients even read and answer emails for you. The whole thing is backwards.

I'm wondering when we'll be at the point where machines will just talk to each other and not notice. If someone sends me a copilot written email, and my Spark AI+ then summarises it, and forwards it to someone who has Superhuman distill the core points, are we even still sending letters? Is that what email is coming to?

Maybe. Some might even welcome this, and trust me, I get it. Email is first and foremost an annoyance we have to deal with. I get that, and many see it as not an art form but the necessary turn based combat of the office. And, for that, sure. Outlook is fine.

But I digress. I simply can't believe there's not a single good email client out there. Not a single one. MailMate comes damn close, but IMAP only and Markdown only for composing is probably a step too esoteric for mainstream adoption.

So, what do I want? Honestly, I want Eudora back. But failing that, my demands are as follows: a native app, with support for all IMAP features like keywords, expunge and redirect, but also Gmail, Exchange, and whatever Apple is doing. Customisable UI, auto-detection of mailservers, Thread Arcs, my dog back safely, and a promise to not enshittify it with core baked-in load-bearing AI features.

Course, no one's making that. But can't a girl dream?