Hotmail / Mac Mail -spotty and now totally unable to login

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Level 1

16 points

Hotmail / Mac Mail -spotty and now totally unable to login

Ok I;m on Mojave / Mac Mail, multiple Macs, one Iphone.

Hotmail works no issue on phone. Able to login via the web to outlook no issues. Problem is only with the Macs. Followed every troubleshooting page I can find on the net -no success.

In one of those it asked for delete account and re enter. I did that and Keychain pulled it off all my macs and now can not re-login at all. The error message is consistent "unable to verify account name and password". Same message was showing over the last few months off and on as it petered out. When it didn't want to work it would ask for the password relentlessly. Put it in and sometimes would work and sometimes not. Eventually it stopped taking it. There were times when the mail would download to the macs but you could not send out. It was just moody until it quit entirely.

I've created new passwords, deleted plist files and everything else that was suggested on the net.

Here's the thing, I have another hotmail account which I don't really use anymore but it still works. For kicks I set it up using the exchange option in mac mail and works like a dream. Keychain populated it to other macs, all bueno. Works great so to me this eliminates hardware and software as issues being too old or not able to function, or MS changed something that now doesn't jive with older mac mail.

I don't have outlook software so mac mail is my only option.

So I'm lost now. Any last ideas for something to try?

Posted on Sep 10, 2024 5:13 PM

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Answer 1

Top-ranking reply

mxracer700 Author

Level 1

16 points

Sep 11, 2024 3:06 PM in response to BDAqua

Hi BDA,

Non working account is IMAP. I've tried many many times to establish the account again using both the Exchange and "Other" email account options on my Mac's to no avail. However YOUR SOLUTION WORKED!!

To be clear for others reading this, once you have two factor enabled for your hotmail -done by being logged into account.live.com not your regular hotmail page. Make sure to use another computer you've never logged into your hotmail or outlook before via the browser and then create an "app password". This is under Security > Manage how I sign in > App Passwords > "Create new app password".

Now go back to your Mac -delete the old hotmail account then create it again not using "Exchange" choose "other" Then enter your emaill address and the new app password you created. App pwds are one time use password. If you need another log back in and create a new one.

Thanks BD Aqua for this solution!! This was driving me nuts!

Cheers MXR.

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Answer 2

MartinR

Level 7

24,137 points

Sep 10, 2024 7:28 PM in response to mxracer700

More specifics will help. You first said that you were using Mojave/MacMail then said you had multiple Macs. If you have multiple Macs, please identify each one (specific model, as in iMac, i5, 4k mid-2017) & the version of macOS on each.

You may need to start using an app-specific password in Mac Mail on your old system(s). You can do this by signing into your MS account, navigate to Advanced Security Options to create an app-specific password that you will then need to use in your Mac Mail account setup for your hotmail account.

It's also possible that Mac Mail on your Mojave Macs doesn't support current email security protocols required by MS. If the app-specific password doesn't fix the problem, let us know and we'll explore further.

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Answer 3

BDAqua

Level 10

250,253 points

Sep 11, 2024 11:54 AM in response to mxracer700

If the non working account is IMAP then delete that account & start over by ading it using other, then using a Browser that has never logged in to tat accouunts WebMail to get the App PW...

Most likely biggest factor is using Other in Mail setup, then using a Browser that doesn’t have Hotmail PW stored init to get the App PW.

Changed Yahoo password, yahoo stopped sen… - Apple Community

Using app passwords with apps that don't support two-step verification (microsoft.com)

What about application passwords? Will that keep working?

If application passwords are being used for MFA (Multi Factor Authentication) along with basic auth as another auth mechanism, then when basic authentication is disabled, app passwords used for MFA will stop working too.

Where can I find more information?

There are several resources that we wanted to provide here as additional reading:

Basic Authentication Deprecation in Exchange Online – September 2022 Update – this is a comprehensive post containing more information about this effort.
Deprecation of Basic authentication in Exchange Online – our official documentation related to this effort, with links to much more information and guidance.

https://techcommunity.microsoft.com/t5/exchange-team-blog/exchange-online-email-applications-stopped-signing-in-or-keep/ba-p/3641943

Exchange Online email applications stopped signing in, or keep asking for passwords? Start here. - Microsoft Community Hub

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Answer 4

mxracer700 Author

Level 1

16 points

Sep 11, 2024 8:50 AM in response to MartinR

HI Martin,

You're a saint for taking the time to help me.

So I tried the app specific pwd and no go. Generated two different pwds and no luck, same message -unable to verify.

So I have two mac minis late 2012 running 10.14.6 and an Air -early 2014 running same OS. That said in my small brain I'm thinking because I have another hotmail account which signs in and runs on all devices with no problem that negates any worry about compatibility, protocols etc. It's just one particular hotmail that won't authenticate. Given that it works for one account and not another Apple is going to say it's not us and Microsoft (if there was any way to get ahold of someone) is going to say it's an Apple issue.

My expertise is just enough to be dangerous as they say but I am thinking it has something to do with keychain.

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Answer 5

BDAqua

Level 10

250,253 points

Sep 11, 2024 4:08 PM in response to mxracer700

Good work my friend.:)

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Hotmail / Mac Mail -spotty and now totally unable to login

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