Apple Mail, Hotmail/Outlook, and an Illogical Standoff between Apple/MS

For the longest time, I’ve been very happy with my email setup on my MBP, Microsoft Outlook for my work email, and for everything else.

When I purchased my first Mac in late 2013, Apple Mail did not officially work with hotmail. At that point in time, it was not an issue for me as Gmail was my main email account. As my trust in Google waned, I gradually found myself shifting to using my hotmail email address as my primary email account.

Fast forward to 2018, Apple Mail still does not work well with hotmail. Mail can still download my emails from the hotmail/outlook servers, but I can’t seem to send anything through the client. I tried a bunch of fixes, and I even tried setting up the account anew, I created an app PW, updated the ImPA and SMTP settings. Nothing worked. I know (and heard) that this is more Microsoft’s fault rather than Apple. That’s when it hit me, I should not be jumping through hoops to try and set up an email account. This was not right.

I decided to move to Spark, and I set up all my personal emails on Spark in less than 5 minutes. I will miss Apple Mail, not a lot. But I’ve come to the conclusion that I was fighting a losing battle. What frustrates me even more is that iOS mail has no issue at all working with hotmail!

At a time where the battle of the platforms has to a large extent been made irrelevant, and where big SW companies are competing on value add services, it still puzzles me that this hotmail/Apple mail issue still exists!

In my experience, Apple Mail is losing it’s grip for a long time already. Their IMAP implementation is prone to errors and very slow. Things I’ve archived already in the web interface would still be in my Inbox on mac, and so on. On my mac, I am using Mail for gmail - not a pleasant experience. On my iPhone, I am using it via exchange for corporate mails - again, it is not up to the task of having a huge account with a lot of folders. Everything feels clumsy and slow. Since email is not a “sexy” technology you can sell I doubt we will see any improvement here soon.

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Hmm I wonder if this is a matter of the server … haven’t had any issues with Fastmail IMAP & Mac Mail for over a decade.

It’s a standoff between Apple and Microsoft that goes back a long time. You can’t get mail or calendar support from on the Mac platform, except if you use the Outlook app.

I’d place the blame fully on the side of MS if other email clients such as Spark and Airmail did not support, both setting it up as IMAP.

Also MS shares the IMAP settings on, screenshot below.

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Are you still having this issue? I’m a Spark user and just wish it showed more emails instead of taking up space with the preview.