Anectodically, I tried to get support for something unrelated: I’m trying to use IMAP sync support in Outlook.com, but it refuses to work properly with iCloud-IMAP but doesn’t give any error message either. As a paying M365 subscriber I expect proper support. I tried over five times to get support, and every time it ended in frustration. Every time I got someone who either doesn’t understand to product, says IMAP support is not available and deprecated (it is not! I was able to set-up a different IMAP provider just fine), or I got redirected to the Windows or Office support team, who then couldn’t help me and closed my ticket.

I cannot prove it, but I bet there is an internal number of replies before they can close without penalty.

What’s left?

Some issues are also due to the ecosystem itself. Avoiding POP3 goes a long way for example.

There are too many variants, all only vaguely compatible.

The iOS integration requires enrolling one’s phone in the email provider’s MDM, at least to some extent. This is nice if you’re an admin, but it’s not so nice if you’re a user who uses (in accordance with company policy!) a personal device.

The integration with Mail.app is abysmal. It makes my memories of Eudora seem happy.

Signing in is a real PITA.

The spam classifier is comically poor. I’m honestly surprised that (hundreds of) millions of dollars aren’t lost every year when a (paying, enterprise) customer emails someone at a different business (from the native app!), they reply with an utterly non-spammy reply, and the reply is classified as spam. Seriously, the open source spam classifiers from the early 2000s understand threading — how can Microsoft fail to classify individual replies as not-spam? Google is far better. Fastmail is far better. Everything is far better.

I will give MS some credit: the iOS Outlook app is actually pretty nice.

Outlook debuted Cached Exchange Mode in the early 00s, popularizing "offline first" before it was known as that.

Now: The "new" Outlook can't even show folder unread counts correctly, even when fully online. It seems to only load a small subset of messages locally, only populating folders when you scroll past the point it loaded. (In classic Outlook, this was a setting—I understand loading all mail was not enabled by default—but it could be enabled. No longer.) It sometimes gets stuck where it won't show new mail until restarted. (Gmail has this bug too.) It forgets open mail windows when restarted. It forgets expanded folders in the folder pane when restarted (but only sometimes).

Microsoft removed the ability to show the mail/contacts/calendar navigation bar below the folder pane, and forced it to be shown on its own huge vertical bar, almost all of which is wasted space. For good measure, they did this in classic Outlook as well as "new" Outlook. There was massive backlash to this, and Microsoft plowed forward anyway. On Windows there is/was a registry setting to revert this (but intentionally, no user-facing setting). I have not checked on Mac.

To the sibling comment: Outlook for iOS is indeed great, probably only because it was an acquisition. It is not in Microsoft's DNA to build an app like this themselves anymore.

As an admin: Microsoft seems to redo the Office 365 admin interface every 2-3 years. It is an incomprehensible mess. I am also a Google Workspace admin for the past several years, and theirs is far better, and it's more or less stable over the long term.

Office 365 has been hacked by state actors recently.

I still like the Outlook UI and feature set better than Gmail (despite the "new" Outlook being a major regression), so I begrudgingly stay with Outlook/Exchange because I dislike it less than Google Workspace.

Fastmail does not give signs that they are a relevant company—they created JMAP and basically did nothing with it. Why not make a first-class Windows/Mac client, offline first, with powerful organizational features, like the Outlook of yore? Or at least, contribute to adding first class JMAP support to Thunderbird? This is your sole business.

It really is a tough choice. Microsoft does have the best products for their and mobile platforms (including iOS,iPadOS) with really good Offline Features and so on. But it still is Microsoft and Exchange behind...

A better product is Fastmail. But also US Servers and AUS company and a lot of downsides concerning offline usage and other privacy points.

What else? I try to avoid Google as much as I can.... Well there is Proton with it's Proton Suite getting better and better. There is german mailbox.org (worse 2FA) but overall a good privacy mail provider with own domains. There is migadu.com from Switzerland with EU Servers (rented at OVH Data Centers) and some other players like Tuta and others...

At any point of this century, the response to those support incidents from MS was always to deny a problem, and if it's a known one, to try to gaslight the customer in a direction contrary to solving it.

I have seen organizations lose way too many people-hours trying to satisfy the MS support and apply what it recommended. That when the real solution was often reachable in a hour or two of research on 3rd party knowledge bases.

Sadly the hotfix had its own little bug: installing it took about 20 hours. Office productivity was rather low for the rest of the day. I don’t know everything that goes on under the hood with Microsoft’s installers, but wow they’re slow.

I, blissfully, don’t use Visual Studio on Windows any more :)

I remember being astounded by the technical depth of a particular answer and looking up the the engineer on LinkedIn. He had 20+ years of experience at Apple - and it showed in his answer.

[0]https://mullvad.net/en/blog/bug-in-macos-14-sonoma-prevents-...