Email Woes and Apps

Here I am writing a blog post, like it’s 2004! And what am I writing about? I moved in to a new email app. This really feels like blogging circa 2004. Partly because blogging, but also 'cause I haven’t felt like I needed to think about email applications in about that long. But – web apps being web apps, and the internet of today being what it is – here we are again.

Over a decade ago, I moved into GMail. It was great. At that point, fully immersed in the life of a junior faculty member and constantly drowning in email, I thought GMail was the best possible solution: keep this horrific mess off my own laptop and on somebody else’s server, and just let me to look at it through a window when I need to, instead of feeling responsible for the whole thing. It didn’t hurt that GMail featured an absolutely best-of-breed UX: it felt seamless to use, had all sorts of keyboard shortcuts, and the search function – well, let’s just say GMail search was first rate. Anyway, I auto-forwarded my institutional email address into GMail and never looked back.

Until a year or so ago, when my institution, like so many others, decided that they were going to move lock-stock-and-barrel into Microsoft’s enterprise systems. The forwarding still worked for a few months, until the IT people sent out a notice that, for security reasons, they would no longer allow it. So early in 2024 I had to bite the bullet and move into outlook.office.com.

My transition to Outlook was predictably bumpy. It took a week or two of getting used to the layout and typography differences (and the mostly useless settings/configuration for these), but I figured: half the world uses this app, so it must be at least usable, once I get used to it.

But it wasn’t, really. I got used to the typography, but the UI is just janky. Clunky. The people who wrote this app spent nowhere near the time that the GMail team spend refining the UX for theirs. The search is only partially usable. Nothing quite works the way you expect (even though I could get it to use GMail’s keyboard shortcuts). Nothing is smooth. The set of actions this UI seemed designed for was somehow not the same set of actions I performed trying to get through my inbox each morning. This did not surprise me, given my experience with other Microsoft apps, like Word.^[1] I still felt no real loyalty to my email and so figured I’d just get used to it.

But then it got worse somehow. Over the course of 2024, the UX has seemingly degraded. I can’t quite account for it, but it’s just shit now. The app loses focus all the time; my cursor disappears or gets locked up. If you copy and paste something, you end up caught in sort of clipboard holding pen, unable to type. If you create a web link in the text of an email, you can’t type past the link; you’re trapped there. Weird stuff would just happen, and you’d find yourself several steps back, starting again. And it keeps trying to put my “attachments” in OneDrive! I don’t know what Microsoft is playing at (actually I do: it’s AI), but this sucker is just useless.

So, what to do, what to do? One option was to install the native Outlook app on my Mac, but I didn’t feel good about that: either it was likely to be just as bad as the web UI, or the web UI was deliberately broken in order to drive me to the desktop app (and why… for better AI/tracking purposes?), so I didn’t feel good about that option. But my institution did say that IMAP clients would be “partially supported,” noting Apple Mail and Thunderbird as options.

This felt like going back in time. I thought I’d left desktop email apps behind in 2013 or so. Here I was looking at going back! And so, I set up Apple Mail (thanks D’Arcy), and synced it, and it appears to work, and the UI looks like it was designed by people who knew what UX is, at least. We’ll see.

What’s weird, though, is that this past week I also installed NetNewsWire, an RSS reader app (from the old days!) as an alternative to the slightly janky, slightly suspect web-based RSS reader I had been using. Again, back to the future. NetNewsWire is great: it’s much as I remember it except a decade more evolved, and smoother than ever.

So I find myself in a strange world where, having championed the web as the universal platform for so many years, I now find myself turning away, because the web as a platform – at least the corporatized part of it – is so… compromised?

Email is and always has been a weird mixed blessing. It works stupidly well: so well that it ate the world, or at least the institutional world, to the point where most institutions are just big masses of email going back and forth. The supposed rise of a second order of messaging apps (Slack and Discord and Mattermost and whatever) was a nice break, and supported some things better (like endless banter), but nothing is likely to unseat good old email any time soon. As a faculty member at a big university, I spend a substantial portion of every single day dealing with email; I both love and hate it. The infrastructure that supports this is actually important! So I’m sad to be flailing with these apps.