I’ve complained about Microsoft on this blog many times, and it’s no secret I’m not a fan of Outlook. If you’ve been reading my blog for more than a few weeks, you’d know by now that I must use Outlook for work, and that my workplace blocked third-party integration for Outlook. So, today I explored the more specific annoyances I have with Outlook, and if it’s possible at all to get my email integrated into Emacs somehow, even with a workaround.

The specific annoyances I wrote down are:

  1. Most of my tasks today come from emails, and it’s annoying to copy-paste from Outlook into org-mode. Further, Outlook has a way of messing up copy-paste sometimes, and I end up pasting double spaces or text from other lines I didn’t highlight.

  2. Outlook’s UI (as well as most Microsoft products) is somewhere between unintuitive and a problem that stops me in my tracks and prevents me from working. There are plenty of examples, but here are a few:

    • I can’t find an attachment I need in an email conversation that consists of multiple emails. Even if I’m on the specific message with the attachment (as indicated with the clip icon), it’s sometimes simply not.
    • Replying to an email in a chain doesn’t always work. I can stand on a message, and there’s no reply or reply all option. I need to be on the main conversation to reply. This is a problem because sometimes I forward an email to different people (or they forward an email to me) and the conversation splits while still in the same chain, creating a situation where I logically have two conversations bundled into one “conversation” per the subject.
    • The “focused” inbox is just good enough to trust, so I don’t check what’s in my “other” inbox, and I can end up missing important emails and automated reports.

Learning how services are blocked from integrating with Outlook 365

Since I work for a health center, the big concern is HIPAA and PII. Microsoft is one of the companies that supplies a blanket solution for the requirements of my organization, and that’s why Office is the way to go.

However, there are a few exceptions that I’ve been aware of. For example, Apple Mail on iOS is permitted, and I believe the same applies to some email clients on Android. This makes sense since many people use their own phones for work, and they would not see emails otherwise. Another example used to be Thunderbird, which up to a few years ago was generally allowed. This made me think there’s some sort of selection going on rather than just a big “off” switch for all integrations.

Digging further into admin documents from Microsoft and some meeting notes I was a part of, I was able to piece together that there’s something Microsoft considers “modern authentication capable” apps, which of course includes their various programs. But there’s more to it. Modern authentication ties into 2FA, which we use at work, and we do need. I had a strong feeling that mbsync, which is needed for email integration with Emacs, would not support 2FA, at least not out of the box. That gave me a hard stop: 2FA is needed and necessary, and if I can’t get it to work with Emacs, then I won’t.

Out of curiosity, I wanted to know if it’s the same case for email clients that support 2FA. The new Thunderbird, for example, is supported according to Microsoft’s own documentation. I tried it on Linux, and I was able to log in with 2FA sure enough - but I was prompted with a message telling me that Thunderbird needs admin approval. Ah ha. So some “modern authentication capable” applications are indeed simply turned off by our admins. Thunderbird might be a bit better than Outlook, but the point is email in Emacs.

What can I do with Outlook?

For now, it seems getting emails with anything other than Outlook on my Mac is not going to work. Alright, is there a way we can at least make Outlook less horrible?

It’s possible to turn off conversations in Outlook, an option I don’t remember I’ve seen before (maybe there was a recent update for Office 365 for the Mac recently?). This would show me all the emails in order they were received, and might be a bit confusing at first, but I believe I will adjust and eventually this might be for the better.

Likewise, I saw I was also able to turn off the “Focused” view and have all emails show in one place. This means I will see a lot more emails, and I will need to configure what I want to be out of the way with Outlook rules, which will take a while. However, it would be better to have my own rules for sorting emails into folders that make sense to me. I don’t want Outlook to think for me. My organizational logic works anywhere close to what the Microsoft geniuses think it should be like.

So I will see what next week brings and what improvements I can bring with it. At least I learned a few things about Outlook, and sometimes it’s good to learn more about what doesn’t work for you so you know how to deal with it, I guess.