Microsoft Outlook (Desktop)

★★★☆☆

I won’t say I’ve never liked Outlook, because the macOS version has been pretty decent for a while, and the Android version is at least okay.

But the Windows version has been a series of train wrecks since Microsoft grafted email capabilities onto its Schedule+ calendar software back in the late 1990s so they could bundle it as part of Office. Windows’ built-in mail clients, from Outlook Express back in Windows 98 through Windows 10 Mail, have consistently been better at email than Microsoft’s flagship mail client.

Outlook has always been awkward and cluttered, and it was notorious for security problems back in the 2000s. (To be fair, so was Outlook Express.) And it was terribly unstable. It would just stop working without telling you. Or it would keep running after you closed it (again, without telling you). There was an Inbox Repair Tool, which was good because you were pretty much guaranteed to need it at some point, but you’d have to find it first. I worked for a small internet service provider, and I dreaded the calls from Outlook users because there was so much less to go on than there was with other email applications. Even Outlook Express would usually give you a error message when something went wrong. I stuck with Eudora for my own work email, then Thunderbird until everything was consolidated onto Exchange and I had to use Outlook myself. At least I had plenty of experience troubleshooting it by then.

In the mid-2010s I was working at another company when they switched the software development team from Windows to Mac. I started noticing that Outlook seemed to be more stable (if still a bit of a resource hog) than it used to be, and figured after ~15 years Microsoft had finally managed to make it usable! It’s still not my preferred mail program, but I don’t mind using the Mac version for work most of the time, except when I have to work on email itself, or vet something that looks suspicious but might just be misdirected, which has happened. Thunderbird is better for getting at the raw headers or message body if you can get at the relevant messages from it.

But the Windows version has continued to have bizarre quirks, like using Microsoft Word to render HTML-formatted messages instead of IE or Edge. (Why? My best guess is it was a shortcut to make it stop executing JavaScript in email back in 2007 or something.) I discovered this when, in 2023, I had to figure out why a business email template looked great on every modern email app except Outlook on Windows…where the message was completely blank. The “New Outlook” that launched in 2023 finally switched to the system web engine on Windows (like the macOS version had been doing for years), but business software always gets used longer than you’d expect, and I’m sure there are still Outlook 365 and Outlook 2019 installations out there today.

I should also note: Outlook is still strongly geared toward office (and Office) use, and tying into other Microsoft services. You can connect it to other email providers like Gmail or any random IMAP host, but it would rather route that through Microsoft’s own mail sync if possible. Which does have the advantage that you can see the same mail and accounts on the web version as on the desktop version, but also means you’re routing all your mail through Microsoft anyway (and can introduce more complications).

Overall

Mac: 3 stars for personal use, 4 stars for business use.
Web: 3.5 stars for business use, still too cluttered for personal use.
Windows: 2 stars. Maybe 3 if you’re using the latest version. For business.