How to set up Hotmail/Outlook account with two factor authentication in Apple Mail app?

Den B. wrote:

I have my old Hotmail and a new Outlook email accounts set up with two factor authentication. Both require a Google Authenticator app to generate time based code that I will have to enter if I'm logging in from an unknown device. (On my desktop computer I set them up to remember that web browser so they don't ask for the time based code. It works really nice.)

The way I had these accounts set up on my iPad in the Apple Mail app is by using device passwords that Hotmail allowed me to generate. This worked until maybe 3 weeks ago. When all of a sudden I would be interrupted by this popup:

It would pop up right in the middle of whatever I would be doing at the time and won't let me continue until I manually dismiss it. First off, VERY BAD UI choice, Apple!!!!

So I went into settings and tried to set up my previous device passwords that I was using before. But it kept saying that the password is incorrect. So I had no choice but to use my actual login password for the Hotmail account and then provide a time based TFA code. This had worked for a few weeks until today, when I got interrupted by the same annoying popup! Argh!!!!!!!!!

So how do you set it up to remember that device and not ask for password every 3 weeks?

Per Microsoft:

https://support.microsoft.com/en-us/help/12409/microsoft-account-app-passwords-t wo-step-verification

First off, VERY BAD UI choice, Apple!!!!

Following the Microsoft link given you, I don't see that Microsoft even supports the iOS Mail app. They do not consider it a common app at the very least.

This article clearly states that not all apps will ask for Microsoft's app password the same way. The UI issue you blame on Apple seems to be driven by Microsoft's code for app passwords. Microsoft's code creates the timing of the prompt, not Apple's

https://support.microsoft.com/en-us/help/12409/microsoft-account-app-passwords-t wo-step-verification

I believe the rub is... this is Microsoft's issue to resolve for you.

Deleting the account and adding it back in within Mail with a new app specific password worked perfectly. No matter how many time I tried logging in to the existing account it rejected the new app specific password.

The point is that it used to work until recently.

So who do you think tweaked their code recently? Do you suspect Apple did, just to create this issue?

The response you are getting is from Microsoft's server. iOS just passes it on as received during authentication.

There are some apps that, when authenticating to an Apple service, will take Apple's 2FA code combined with your regular password. Maybe Microsoft's will too.

So if your password is Microsoft123! and a 2FA code is 456789, enter Microsoft123!456789 in the password field. Worth a try. I've seen this called a decorated password.

Then I'll go back and suggest Microsoft, and therefore their 2FA function, does not appear to be supported in iOS.

Even though it did work recently. Microsoft may have seen that as a risk and plugged that hole. It wasn't Apple's to plug.

And like all security-risk-averse companies, I doubt MS will document that in their change logs.

Yep.

The reality in a he-said she-said situation however, is that Microsoft has the responsibility to make their product wok in iOS Mail, not the other way around.

If this were iCloud Mail not accessible in some way within the Outlook client, I'd feel the same.... that Apple would be responsible, using the SDK for Outlook, to make it work.