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New protocols for using Apple Mail with Hotmail accounts

Microsoft has announced the following:

"The safety and security of your information is top priority for Microsoft. To help keep your account secure, Microsoft will no longer support the use of third-party email and calendar apps which ask you to sign in with only your Microsoft Account username and password. To keep you safe you will need to use a mail or calendar app which supports Microsoft’s modern authentication methods. If you do not act, your third-party email apps will no longer be able to access your Outlook.com, Hotmail or Live.com email address on September 16th."

I use Apple Mail for all my email accounts which include two hotmail accounts that need to be redefined as 'outlook' accounts with new security parameters for them to work with Apple Mail, otherwise I am going to lose access to these accounts via Apple Mail. I have Apple Mail installed on all my devices, the principle device being a Mac Mini (Sonoma 14.5). Obviously these email accounts will be available via other email apps like Outlook for Mac and via a web browser.

According to general advice that I have looked for, the best way continue to use Apple Mail is to delete the accounts from Apple Mail (via the Mac Mini) and then add them again with the new Outlook parameters which are not simply the current account name and password. Doing this does not alter any emails that you have stored on the Outlook server - the account name is not changing.

I have all of my mail stored in mail folders on my Mac. I don't keep the messages on the remote server. The only messages that are held on the remote Outlook server are the most recent in my Inbox i.e. those that I have not yet moved to other folders on my Mac and those that have not yet been deleted from the remote server.

So, if I delete the accounts in Apple Mail (on the Mac Mini), I am going to lose all of the history of my emails stored in the various mail sub-folders for the corresponding email account on my Mac Mini. As there is no copy of these on the remote server, they will be lost forever. Adding the new Outlook version of the accounts will not connect these accounts to their history in Apple Mail.

I must admit that I am a bit lost as to how I can continue using Apple Mail for my two Hotmail accounts. The only thing that I can see that I can do is the following:

Copy all subfolders for these email accounts on the Mac into new subfolders for another NON-Hotmail account that I currently use.

Delete the Hotmail Accounts on my Mac, thus deleting all of their sub folders.

Add the new Outlook versions of these accounts with the necessary parameters.

Re-create the subfolders for those accounts and then move all of the previously moved emails back to these accounts.

I understand that deleting and re-adding the accounts on my Mac will be reflected on my other synced Apple devices (iPhone, iPad etc) which don't contain the history, as this is only on the Mac Mini.

I hope I have understood the situation correctly and explained it well.

I don't want to use different apps for my different email accounts. I want to maintain them all in one application if possible.

Any help would be greatly appreciated. There is a distinct lack of information about this one the internet. Sorry if this message is a bit long or is incorrect in any way.

Thanks in advance!

MacBook Pro, OS X 10.11

Posted on Jun 28, 2024 6:49 AM

Top-ranking reply

wlow

Level 1

35 points

Posted on Aug 2, 2024 10:48 AM

I'm not sure if I quite understand what you were saying, but deleting your Outlook account off macOS Apple Mail should not delete mail that you have moved from Outlook to an On My Mac subfolder. Those stay. What is removed is references to IMAP Outlook subfolders and email, which are all in the cloud. The actual subfolder and emails remain in the cloud; those are not deleted either.

The issue and current solution is this:

On September 16, 2024, Microsoft will stop accepting Basic Authentication (email and password) to access your Outlook/Hotmail email via third party clients such as Apple Mail; it will henceforth require Modern Authentication.

I think a lot of people, when adding their personal Outlook/Hotmail accounts to Apple Mail, choose "Other Account" and fill in their Outlook/Hotmail credentials. I believe "Other Account" is a catch-all for any other email service provider; and it will probably only ever offer Basic Authentication. Apple strongly suggests choosing Microsoft Exchange in their FAQ for all Microsoft email addresses, organizational or personal. On iOS, Apple gives both Microsoft Exchange AND Outlook as a choice. They do NOT yet do this on macOS. On MacOS, you must choose Microsoft Exchange.

So if you currently have a personal Outlook/Hotmail account set up under "Other Account," delete it. This will remove all references to it in Apple Mail. Set it up again, but choose Microsoft Exchange. Then choose "Sign In," not "Configure Manually" -- the latter will result in an error. Microsoft will ask you if you mind Apple having access to your account (Apple Mail needs this access to work), confirm and all of your email and subfolders will repopulate in Apple Mail. Your folders will say Exchange instead of Outlook but everything else will be the same. Deleting/flagging email in macOS Apple Mail set up under "Microsoft Exchange" will correspondingly delete/flag mail in iOS Apple Mail set up under "Outlook" without issue.

Until Apple adds an explicit Outlook choice in macOS Apple Mail, this is the only solution. The good thing is that it works and you will no longer have to keep signing into your Outlook account in macOS Apple Mail.

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74 replies

Dirk7

Level 1

8 points

Jul 6, 2024 1:30 AM in response to Munsterlanders

Experienced same problems. Simple solution was to delete the hotmail account and reinstall it with help of MS Authenticator approval instead of password.

Jul 13, 2024 7:56 AM in response to Munsterlanders

Tried to remove and then re-add my MSN Mail account in the iMac mail app. Still doesn't work, and *bonus* ... all of my mail is gone ... sent, saved, inbox, etc.

Really awesome.

Aug 11, 2024 5:46 PM in response to kfreddmd1

An update:

I have followed the Microsoft recommendations along with suggestions on this thread. I have been successful on my Mac via adding all my accounts using the exchange option in the Mac Mail app. On my iPad I added all my Hotmail accounts again in the Mail app using the Outlook option. I also installed the Outlook app for iOS on the iPad and all accounts were added there as well. On my iPhone I did the same regarding the Outlook app for iOS adding my accounts, and also adding the Hotmail accounts via the Outlook option in the Mail app. All my accounts are syncing between all devices and accounts. I have run into one problem with one account however, and don’t know how to fix it.

On the iPhone, the last Hotmail account I attempted to add in the Mail app using the Outlook option(and of course it’s my main account), when I go to input the email address and then the password, I get a message saying “ Cannot create account. An identical Outlook account already exists.” This is the same process I followed when adding 3 Hotmail via Outlook accounts on iPad Mail app after these same 3 had been previously added to the Outlook for iOS app on the iPad. On the Outook for iOS app on the iPhone, these same 3 Hotmail accounts had been previously added, and 2 of these same Hotmail via Outlook accounts had been successfully added already to the Mail app. It’s only that very last one I attempt to add that consistently gives me that “ account already exists” message. Any ideas on how to fix this? Thanks

LV2219

Level 1

19 points

Jul 4, 2024 8:39 AM in response to Munsterlanders

What about moving email archive to folders/mailboxes under the group "On My Mac". Aren't these local folders that would not be affected by removing the account and adding it again? Of course, the archive can only be seen on Apple Mail, but personally I don't mind. And this seems safe to me. Hoping I got this right before removing my account...

Jul 5, 2024 12:00 AM in response to CV350

I am currently using the outlook app in my Macbook pro which is the quick fix.

But yes I wish to have all in the apple Mail app to store all important emails in my laptop than in the cloud server of outlook.

Gmail has 2 way authentications too but it works fine in Mail App for now. Not sure why Outlook can not support Mail app.

Jul 5, 2024 8:14 AM in response to Munsterlanders

It might be better to move away from Microsoft and any other free email services. If it's free you're the product. This will affect me the same way and I'm going to slowly migrate to a new account away from MS.

LV2219

Level 1

19 points

Jul 10, 2024 1:10 PM in response to anittaribeiro

@anittaribeiro I don't usually flag emails, so I don't have much experience with it, but I just tried and it seems to be working OK. But I might be taking this at a more basic level than what you are trying to do

Jul 23, 2024 9:45 AM in response to Stan Fowler

I think you must have had all your emails stored on the remote server, not locally. If you remove an account from Apple Mail, I understand that all of the local folders under that account are deleted. Therefore, if copies are not held remotely on the Hotmail server, they are gone forever. I am in the process of saving the emails in the local Hotmail accounts, locally in Apple mail, but not as sub-folders of the Hotmail accounts. I will then try to delete and add the Hotmail accounts again choosing Microsoft Exchange. If that works, I guess it should be possible to move the 'saved' emails back into new local sub-folders under the Hotmail accounts. Who knows! If not, it may be time to give up on Apple Mail, bite the bullet and use Outlook!!

Jul 23, 2024 11:33 AM in response to Anne.Onnimus

Good advice Anne. Save everything before attempting to delete and re-add the account as a Microsoft Exchange account. I have no idea how this is more secure because as I understand it, it is still just an email account and password. When you deleted the account and re-added (presumably in Apple Mail on a Mac, were the changes automatically reflected on other links Apple devices or does this need to be done per device?

Jul 23, 2024 11:56 AM in response to Munsterlanders

Munsterlanders, Good question! I think you have to do it device by device. I'm using the Outlook app on my iPad, rather than Apple Mail. I don't care whether the emails are preserved on my iPad, but I definitely want my email files on my Mac. I got the result I wanted on my Mac by using Microsoft Exchange. Apparently, it has modern authentication built in.

Do you think Microsoft will send us another warning right before D Day to anyone who is still using Basic Authentication? It might be a good idea to export our Apple Mail files to mbox right before D Day in case there we get cut off.

Jul 25, 2024 9:54 PM in response to Munsterlanders

I am experiencing the same dilemma and Microsoft's instruction to avoid the problem they're causing does not work. My MacBook Pro (Retina, 15 inch, mid 2015) running MacOS Monterey 12.7.5, according to Microsoft and Apple, Apple Mail supports OAuth by default when you setup the account as Outlook.com. Microsoft's instructions issues: described for iPhone, deleting my hotmail account is not an option is it will delete 10 years of emails saved in folders on my computer, and drop down menu for setting up a new account does not show Outlook.com as an option. I'm in the SAME situation as Munsterlanders descrbed above. Someone wise in the ways of making microsoft mail account work in Apple Mail on a MacBook Pro Please help! This is the link to the Microsoft guidance for addressing hotmail OAuthority change.

https://support.microsoft.com/en-us/office/outlook-and-other-apps-are-unable-to-connect-to-outlook-com-when-using-basic-authentication-f4202ebf-89c6-4a8a-bec3-3d60cf7deaef

Jul 25, 2024 10:09 PM in response to CitJ

I followed your described process and everything went as described up until "Now before anything else while you're still in Mac Mail Server Settings on the Accounts tab, on the left click on Exchange, the Exchange email."

There was no option on the left to click on Exchange. Thanks for the brief optimism but Microsoft....sucks. Nothing ever goes as Microsoft thinks. https://support.microsoft.com/en-us/office/outlook-and-other-apps-are-unable-to-connect-to-outlook-com-when-using-basic-authentication-f4202ebf-89c6-4a8a-bec3-3d60cf7deaef

Jul 26, 2024 1:06 AM in response to KuKuKaChu007

Thanks for posting the link KuKuKaChu007. One blatantly obvious problem is that "Outlook" does not appear as an options for one of the types of accounts to add (at least not on a Mac). Maybe it does if you are trying to manage the mail from iPhone but my main use is on my Mac. I am running Sonoma 14.5 on a brand new Mac Mini, so there is no issue here with out-of-date IOS software etc. I have a feeling that community users who have successfully deleted and re-added their account using "Exchange" are just continuing in the previous way and will lose access in September. It would be nice if someone from Apple could confirm whether or not Apple Mail supports "Oauth" authentication. Reading the Microsoft material, it seems that this is more that just your email account and password, so what is the additional layer of authorisation and how do you define it when adding the account to Apple Mail if the option to add an "outlook" account doesn't appear? I'm getting closer and closer to accepting that this will not be resolved and that moving to Outlook for Mac is the only solution, whilst leaving the history of the Hotmail accounts stored in local folders in Apple Mail. Not ideal but.........

Jul 26, 2024 1:41 AM in response to Munsterlanders

It would be nice if someone from Apple would just say if they’re addressing this! I can’t imagine any other corporation ignoring a claim from a leading rival that their security system is broken!!

I’ve spent a lot of time this week trying to migrate from my live.co.uk email and Apple User ID to an icloud.com one. I gambled on deleting my live.co.uk mailbox on my Mac to an Exchange one. I’m no longer getting those annoying ‘enter password’ prompts but I’m far from convinced that this will work after MS’s September deadline.

So I can get mail on my Mac from the live and icloud mailboxes BUT I can’t get my iphone or ipad to add the icloud account to ios Mail!

I can't be the only previously devoted Apple user who’s losing faith in them due to their complete indifference! Grrr!

Jul 26, 2024 7:14 AM in response to Munsterlanders

This was only an issue with my iMac running Sonoma 14.5. No issues on my iOS devices (iPhone, iPad).

I removed my MSN Mail account, which was set up as an MS Outlook account. I then re-added it as a Microsoft Exchange account using the same credentials.

The issue of 'enter your password' has been resolved, and all my folders are intact.

I'll try doing the same with an old Hotmail account, but I rarely use it and the problem hasn't been as pervasive.

New protocols for using Apple Mail with Hotmail accounts