Mail on MacBook constantly unable to recognise Hotmail account name & password (and app-specific password)

You have to update to Sequoia

Does that still work for you?

I had the issue and thought I should try enabling 2-factor with app specific password which worked up until I close the mail program. Upon reopen, immediately asked for password and won't connect.

I disabled 2-factor and deleted app passwords and it won't log in at all still.

This happens with Apple Mail app and my Outlook for Mac app.

Very frustrating...

I can log in using a browser via Outlook.com and my iPhone mail works like the OP stated but I can't use my computer apps at all.

It is shocking to see the lack of interest on the part of Apple to support Outlook accounts. Very disappointing. I too will be migrating to Outlook and not looking back to Apple Mail which I have been using for more than 15 years.

I have tried to follow that original poster's steps but Mail still won't work. The additional information I can provide is that:

1. Mail (hotmail in Apple Mail) has worked for several days since I upgraded to MacOS Sequoia;
2. Deleting and recreating the account seems to work for some time;

Hi! Thanks for the tip but I have already tried this -- no success. I have, temporarily, "migrated" all my Apple Mail accounts to MS Outlook but do intend to return when/if Apple fixes this issue for good.

Hi Marielle. Well, same here: using MS Outlook (part of Office 365) and getting used to it. I still think Apple Mail is better (because I'm really used to it ater so many years) and would like to go back to it; I'll wait for MacOS Sequoia 18.0.1 or later to fix this but from what I have read in this thread they aren't likely to fix this.

Thank you for replying!

-Fernando

Hello there,

It seems that I am in a bigger mess :)

I am using two very old vintage devices ... a MacBook Pro mid 2012 running Mojave and an iPhone 6s running IOS 13.

For a couple of months I started having this problem to the point that on my Phone there were times when I had no mail :) everything disappeared, even older mails. Interestingly, when I went abroad (I am based in an European country and went to another European country), the Mail on my phone would sync.

On my Mac, it worked on and off. I have not upgrade to Catalina (which seems to be the most advanced OS I might get, because I have an Adobe Acrobat Pro that works. I do not want a monthly / year subscription. I am thinking of getting Adobe Pro 2020, but I will see.

So, on my Mac, the Mail worked on an off. It would ask for the password when I was changing the WIFI, ie taking the laptop with me and connecting to a dffferent network. Or sometimes after the screen was locked.

Anyway, since yesterday it stopped connecting completely.

I moved to Outlook 2019. I have worked with Outlook before so there is no big problem.

I have two questions:

1. Why do I have more drafts on Mail Mac then on Outlook desktop or on my Hotmail account on the web? The difference is around 30 draft. As if I have some on my Mail Mac even if they are supposed to be synced
2. If I upgrade to Catalina, does my hotmail account on Mail Mac, which is installed as an Exchange, would be working? It seems it would not from what you write.
3. If I get a paid account on hotmail (I have very little space since last year when they change the size), would it work on Mail Mojave?

You may be wondering why I am not charing my Mac :) Beside money matter, I LOVE mine, because I have two hdd on it. It is the old fashioned one, with a CD. So I have a 500 SD on which I am running th system and the apps and a 2 TB hard drive for files etc. AND 16 gb MEMORY, as I could upgrade it.

Newer Macs go up to 1TB from what I know and I want local storage = not clouds and not external hdd as it is annoying to always have cables connected.

One more thing - yesterday I put on the two factors on a different hotmail account (I have not used on Mail) and try to install it on Mac Mail as Exchange account, but it did not work.

I have a newer iPhone 14, I am not yet using it as I hate the luminosity of the display (no. matter how hard I try to make it have the same one as my iPhone 6s does not work) and I installed my main hotmail account in its Mail app and it worked immediately, just with the normal password as it allowed me to install the mail as Outlook.

But from what I read here, even in the latest OS for the newest Macs the Mail app of Apple does not allow adding hotmail as Outlook? Is this what you are saying? And if this is the case, can we know why? I mean, if it allows this on iPhones, why not on Macs?

Fix this please, or else i will switch to outlook app too! It was constantly taking down my account to offline and i have to relogined.

I got tired and changed my password, then it no longer starts to recognize new password, and i don't remember the old password, because you updated the password in your Password app for me!

Well, looks like I spoke up too quickly. I have just opened my Mac to see the "Enter Exchange password" request. However, it's now back to the pre-Sequoia behavior: I just click "Continue", it opens up System Settings but does NOT ask for the password and, of course, does NOT fail to authenticate. It's annoying, but it's working.

-Fernando

I have just tried this and I got a message saying that the certificate for the browser was invalid and I ran the risk of connecting to a server that could put my data and information at risk! Really struggling to get my mail app working again.

I had logged out of my account on the mac mail app but now it wont let me log back in even though I can log in through a browser so my password is correct as well as my iphone. I am frightened to try to change my password in case I get logged out of these other places. The mail app is only showing emails up until July 2021!?!?

I need help!

Are you still able to get mail with the macOS Apple Mail app since you removed the two-step authentication?

Thank you. This solved the disconnecting issue.

[Edited by Moderator]

It’s incredible that these unacceptable issues with Outlook/Hotmail have not been fixed even in Sequoia. Is Apple really trying to push users to MS Outlook???

Yeah. Still not fixed on Sequoia.

[Edited by Moderator]