Does Apple Mail (Sequoia) support Modern Authentication for Outlook personal accounts

[wlow3]

Microsoft has been warning people with personal Outlook/Hotmail accounts that it will no longer accept Basic Authentication (email address and password) starting in September for those accounts from email clients. The email client must support Modern Authentication (not sure what that entails). In their example of iOS, they tell people to delete their account from the email client and then choose Outlook specifically from the Add Account. This is not offered in Sonoma. Microsoft Exchange is listed as a named option in Sonoma but not "Outlook." Previously one could add Outlook or Hotmail by entering an email address and password under Add Other Account, but I think this just uses Basic Authentication.

Can someone who is currently running a beta of Sequoia tell me whether Outlook now shows up by name as an option in Add Account? Thanks.

 

[LinMac]

I can say Thunderbird works as expected. I haven't tried Apple Mail yet

 

[wlow3]

I can say Thunderbird works as expected. I haven't tried Apple Mail yet

If you’re running Sequoia, can you go into Settings | Internet Accounts and click on Add Account to see whether Outlook is now specifically listed as an option?

 

[gilby101]

Microsoft Exchange is listed as a named option in Sonoma but not "Outlook."

Does Exchange not work with Sequoia? That is what is needed with Sonoma.

 

[wlow3]

Does Exchange not work with Sequoia? That is what is needed with Sonoma.

It does. But when I tried it, and I entered my personal Hotmail email address, I got a message from Microsoft within the Add Account process that said Exchange is not intended for personal accounts. So I just want to know whether Outlook is listed explicitly in Sequoia like in this image Microsoft uses in its FAQ (which I think is from iOS).

 

[artguy10]

Microsoft has been warning people with personal Outlook/Hotmail accounts that it will no longer accept Basic Authentication (email address and password) starting in September for those accounts from email clients. The email client must support Modern Authentication (not sure what that entails). In their example of iOS, they tell people to delete their account from the email client and then choose Outlook specifically from the Add Account. This is not offered in Sonoma. Microsoft Exchange is listed as a named option in Sonoma but not "Outlook." Previously one could add Outlook or Hotmail by entering an email address and password under Add Other Account, but I think this just uses Basic Authentication.

Can someone who is currently running a beta of Sequoia tell me whether Outlook now shows up by name as an option in Add Account? Thanks.

I have the exact same question. I was just wondering it last night. On iOS Outlook exists as an option, but on Apple Mail on Sonoma it's starting to get login issues and will need the new Modern Authentication, yet without Outlook being an email option on Sonoma it's not clear what the options are except using other software. Possibly there could be something involving turning on 2-factor authentication and setting up a custom password for the Apple Mail app but I'm not sure if that would solve it, but in any event there seems that there should be a proper option to log in as there already is on iOS. So like you, I am similarly curious if Apple has added this in Sequoia. If they haven't, then that seems to be an odd omission given how many people have Outlook email addresses and this being a requirement and Apple having already properly implemented it on iOS.

 

[gilby101]

yet without Outlook being an email option on Sonoma it's not clear what the options are except using other software.

Use Microsoft Exchange type. Certainly works with Apple Mail for me with macOS 14.5 and Sequoia Beta 4.

 

[artguy10]

Use Microsoft Exchange type. Certainly works with Apple Mail for me with macOS 14.5 and Sequoia Beta 4.

I understand that it works for you right now, but using basic authentication also works for me right now, and it seems using it as Exchange may not work reliably either, apparently, and it's unclear whether that will work after the September 16th, 2024 deadline.

Microsoft's instructions specifically say "Apple Mail supports Modern Authentication by default when you setup the account as Outlook.com" and Outlook.com simply is not an option on Apple Mail on macOS. So the official right way to do it is not a possibility at this time, apparently, unless it shows up on Sequoia in the specific way that wlow3 asked about if you were to choose an option to add a new email account and see if it matches their screenshot?

Using an authenticator app might work according to that one person though.

 

[gilby101]

Microsoft's instructions specifically say "Apple Mail supports Modern Authentication by default when you setup the account as Outlook.com" and Outlook.com simply is not an option on Apple Mail on macOS. So the official right way to do it is not a possibility at this time, apparently, unless it shows up on Sequoia in the specific way that wlow3 asked about if you were to choose an option to add a new email account and see if it matches their screenshot?

Experience suggests that is not wise to expect MS instructions for Macs to be 100% correct. At a guess that documenter used an iPhone and assumed that Macs would be the same.

and it seems using it as Exchange may not work reliably

I had come across that link and discussion. To me, it seems like a panic response to the MS changes (which I initially shared). Maybe I had no problems with the Exchange type because I already had 2-factor auth enabled on my Microsoft account using 1Password as the authenticator app.

I can only repeat that adding an outlook/live/hotmail email account using "Microsoft Exchange" type works as expected on macOS 14.5 and 15.0 beta 4. Whether that will change with the release 15.0 is, of course, unknown. But there doesn't seem to be any need for it to change, except to document the steps more carefully.

The only issue I have seen is if I set a coloured flag on the Mac, it is a different colour on my iPhone. Since the web interface for Outlook only has flag/unflag (always red), this may be an Outlook limitation.

 

[gilby101]

So I just want to know whether Outlook is listed explicitly in Sequoia like in this image Microsoft uses in its FAQ (which I think is from iOS).

Not in Beta 4. But since Exchange type works correctly (see my post above), I don't see any need for it.

 

[dotnet]

The Outlook.com option is not present in Sequoia 24A5298h:

However, the Exchange option works fine. It prompts for Authenticator authentication during setup (because that's how my Outlook account is configured), after that it seems fine. I previously used the Other Mail Account option for Outlook accounts, which also works but keeps prompting for the password every day or two.

 

[gilby101]

Apple document this here https://support.apple.com/en-us/102088 near the end:

"When you add an email account to Mail on your Mac, choose Microsoft Exchange for email accounts that end with onmicrosoft.com and for accounts that end with outlook.com, hotmail.com, or live.com."

Rather than "does/will Sequoia support this?" (it works), the bigger question is "how recent does macOS need to be?". I am sure some using old versions of macOS (e.g. my wife with High Sierra) will soon not be able to use Apple Mail for their outlook/hotmail accounts.

 

[wlow3]

I wrote to Craig Federighi, and within 24 hours he responded.

He said, yes, Microsoft Exchange does work for personal accounts.

When I tried it again, I realized my error. I had been picking "Configure Manually," and not the default "Sign In" because I thought the latter was for established Microsoft Exchange accounts. Whenever I did "Configure Manually," after I entered my email and password, Microsoft would always return with the message: "Sorry, but we're having trouble signing you in. User account ******** is a personal Microsoft account. Personal Microsoft accounts are not supported for this application unless explicitly invited to an organization. Try signing out and signing back in with an organizational account."

So this is why I assumed this option did not work for personal accounts. However, just to check everything before I embarrassed myself by replying to Craig that his information wasn't correct, I tried the default "Sigh In," and that returned with a dialog asking me something to the effect of whether I wanted Apple to have access to my Microsoft information. Upon clicking YES, my personal Outlook account (and all its subfolders) was successfully added (although it shows up now listed as "Exchange" and not "Outlook" in macOS Apple Mail). And I got a message from Microsoft Authenticator that this account had been added, which never happened when I used "Add Other" under macOS Apple Mail.

For those wondering: Deleting/Flagging an Outlook email in macOS Apple Mail set up under "Exchange" successfully deletes/flags that Outlook email in iOS Apple Mail set up under "Outlook." This is not an issue at all.

So "Add Other" is really probably just there to accommodate any fly-by-night email provider one may use and probably will only ever provide Basic Authentication. It "works" for Outlook (for now) but is not ideal and if you have a personal Outlook account and you originally set it up under "Add Other" in macOS, I'd delete it from Apple Mail and I'd set it up under Exchange. Then you'll have modern authentication and won't have to worry about the September 16, 2024 deadline.

In my email to Craig, I asked why there wasn't an explicit Outlook option in macOS like there is in iOS. He addressed that only by writing, "We are working to make our UI more clear in this area." So, maybe at some point there will be.

As a side note: I looked at the Recent Activity for my account online at outlook.com and because that email address has shown up in data leaks, there are 20 some attempts a day from sleezeballs from all over the world trying to get into my account. It has a really strong password but I wish Microsoft would reject all attempts from outside my region or move to passkeys.

 

[ksingernc]

Microsoft Exchange is a paid monthly service. I just want my Outlook email to show up in Apple Mail without having to constantly sign back in. If I keep Outlook open in Safari it seems my mail comes through to Apple Mail most of the time but sometimes Outlook signs me out. I set up a new Outlook account which sends and receives mail but when I tried to add it to Internet Accounts the only choice I had was create an Exchange account (since I don't have one) or register the new Outlook account as an SMTP account which I didn't try since it seems those will no longer work after September 16. Sigh.

 

[gilby101]

Microsoft Exchange is a paid monthly service.

As a mail service from MS, yes. It is also the mail "type"/"kind" when you connect from macOS Apple Mail to the free consumer MS mail services with addresses @hotmail, @outlook, @LIVE, etc. But you will need to have configured two-factor authentication with MS.

 

[ksingernc]

As a mail service from MS, yes. It is also the mail "type"/"kind" when you connect from macOS Apple Mail to the free consumer MS mail services with addresses @hotmail, @outlook, @LIVE, etc. But you will need to have configured two-factor authentication with MS.

Thank you for explaining about the 2 factor authentication. I was able to create a new account (JS) with Exchange to use as a test account but things have been really wonky. When I tried to switch my original Outlook account (KS) to Exchange it says that account already exists. When I check in Apple Mail it shows KS as imap, not Exchange. JS shows as Exchange.

All KS Outlook mail appears in both KS and JS mailboxes in Apple Mail but any mail sent to JS only appears in JS Outlook in Safari, not in KS or Apple Mail. Apple Mail shows that JS is online. I'm afraid to delete the KS account and try to add it again in Exchange in case it won't accept it or my KS mail will stop showing up in Apple Mail. I'm still being asked by Apple Mail to enter my password for Outlook which it won't accept if KS isn't open in Safari. I am now using Microsoft Authenticator which works fine for both accounts when needed. I am in a state of chaos and not techy enough to figure out how to fix this. 🤯

 

[PitBullCH]

Can confirm taking the Microsoft Exchange option in Sequoia works fine, no password entered, but confirmed via Microsoft Authenticator - and am able to send/receive emails from/to this account fine. Previously I did have this account configured manually via "other mail account". On IOS via Outlook.com for the same account also worked fine.

Do agree with others: between Apple and Microsoft they really could have documented and facilitated this better.

 

[avz]

On a 2 of October Apple Mail stopped working for me with Outlook. Adding an Outlook account as a Microsoft Exchange comes back with "Too many requests" error. It does not matter if it is Big Sur or Sequoia. Thunderbird works.

Edit: : "Too many requests" error has finally gone and adding an Outlook account as an Exchange worked on both Big Sur And Sequoia.

 

[svkrzn]

On a 2 of October Apple Mail stopped working for me with Outlook. Adding an Outlook account as a Microsoft Exchange comes back with "Too many requests" error. It does not matter if it is Big Sur or Sequoia. Thunderbird works.

Edit: : "Too many requests" error has finally gone and adding an Outlook account as an Exchange worked on both Big Sur And Sequoia.

Mine prompts me for password from time to time and when entered asks for OTP but OTP appears to be always wrong and the only way to fix it is by deleting the acc and re-add it...