Outlook email requires "Modern Authentication Methods", Need correct Mail Settings for POP

Microsoft just sent out an email warning that we must update sign-in technology before 9/16/2024 to maintain email access. The sign-in must be a "Modern Authentication Method".


I use Mac Mail and POP to access my hotmail acct (through outlook.com). It works, but with intermittent authentication failures.


Microsoft's instructions for Mac Mail suggest that I delete and re-add my account. This suggestion is appropriate for IMAP, but with a POP account, I will lose all data (which for POP is stored locally). Microsoft doesn't really provide any meaningful support.


Apple Support has not given a clear answer about settings related to "Modern Authentication".


In Mail's server settings, I see the following Authentication options:


  1. External (TLS Client Certificate)
  2. Kerberos Version 5 (GSSAPI)
  3. NTLM
  4. MD5 Challenge-Response
  5. Authenticated POP (APOP)
  6. Password


I'm currently using "Password". Are any of those options officially considered "Modern Authentication"?



MacBook Pro 16″, macOS 14.5

Posted on Jul 5, 2024 11:35 AM

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10 replies

Jul 5, 2024 3:36 PM in response to stubbsonic

It's not just a simple setting that needs to be "fixed"

'advanced authentication' opens a web browser window and runs secure authentication software to ensure you is you.


While you can certainly try just changing some value using Other setup, I expect you will be back here tomorrow when they shut off access to your account completely, because you did not enable 'Advanced Authentication'.


There are other e-mail services that allow POP, but this one may not be one of them any longer.


IMAP is not a lot different in operation. The email headers headers are presented to you in a list, just liker POP. When you want one, just click on it and it appears, just like POP except it did the download quickily "behind your back"

Jul 8, 2024 12:06 PM in response to stubbsonic

<< So I can just move my hotmail inbox & outbox (sent) into other "On My Mac" folders. >>


you really need to create new mailboxes located "On my Mac" and copy your emails into the new mailboxes.


moving your exiting server-based mailboxes under the heading "on my Mac" will not likely do anything useful.


<< I'm concerned that using this "trick" might inadvertently work-around Outlook's Modern Authentication method.>>


outlook is no longer willing to use the old authentication methods to provide you with email services. IMAP vs POP is a separable issue. IMAP is what you should convert to, and that is what providers are supporting going forward.


<<. Has anyone using POP been successful with this delete then re-add account method? >>


deleting POP account and re-adding MAY delete all your old emails. or maybe not. Works for sure AFTER you convert to IMAP.

Jul 5, 2024 11:51 AM in response to stubbsonic

POP is used by fewer and fewer users, because it does not work properly with MULTIPLE access, e.g., from your phone AND your Mac.


if you do not want to lose your POP emails, You should create a mail folder in the section "on My Mac" and copy all your emails, especially the contents of you inbox, into it, because conversion to IMAP will NOT preserve emails already-downloaded to your Mac using POP.


With IMAP, FUTURE emails are stored on the Receiving Server on the Internet, and only the mail headers are sent to you to look at and choose what to review.

Jul 5, 2024 12:32 PM in response to stubbsonic

stubbsonic wrote:

On my phone, I use a browser to access web-based email server.

Microsoft gives the impression that it might be possible to use POP with "Modern Authentication" but Apple doesn't seem to be up-to-speed on this requirement.

Your suggestion that I'm part of a vanishing minority using POP is true, but I'm not ready to switch to IMAP at this time.


When you add the account back in you can trick the Mail.app to present the POP option...


Remove email accounts in Mail on Mac

Remove email accounts in Mail on Mac - Apple Support


Add email accounts in Mail on Mac - Apple Support

Add email accounts in Mail on Mac - Apple Support


Note—

IMAP accounts stay on the server, so no local loss, when you re-sync

POP accounts download and remove from the server—therefor save your inbox/sent box if you want them

“On My Mac" is just that, local folders you created and moved mail into. So no loss



Mail trick the set up of google/hotmail/etc. mail to present POP.

Use the Other and trick it by supplying a bogus email address.


Once you get the POP option, then edit/add in your correct email address and psswd.


Mail.app—




Jul 5, 2024 5:02 PM in response to Grant Bennet-Alder

Thanks.


Do you know if the "Modern/Advanced" methods will do this every time mail is checked? Or once per day?


Would they shut off access even to my email on their browser based email?


Part of my reluctance to shift from POP is that I often run searches on my old emails, and if I switch, it's not clear how the IMAP works with searches, especially when combined with my many POP/local emails.



Jul 5, 2024 6:48 PM in response to stubbsonic

<< Do you know if the "Modern/Advanced" methods will do this every time mail is checked? Or once per day? >>


The intent is that this authorization is performed once per LIFETIME and never has to be done again. Of course reality may be more often, but not by design. This process generates a token (much more secure that a simple password) that is used minute-by-minute, but I do not have deep details.


Once you is established as you, Email gets checked every few minutes, and having to do this even as often as daily is simply unacceptable.

Jul 5, 2024 6:52 PM in response to stubbsonic

<< Part of my reluctance to shift from POP is that I often run searches on my old emails. >>


my understanding is the Spotlight indexes your emails as they are received, and you can spotlight search for anything, but I confess I do not use that feature directly. I use mail search, in multiple inboxes and it seems to work fine with IMAP.works just fine.

Jul 8, 2024 11:05 AM in response to leroydouglas

“On My Mac" is just that, local folders you created and moved mail into. So no loss


So I can just move my hotmail inbox & outbox (sent) into other "On My Mac" folders, and they will be preserved even if I delete my hotmail account? That seems easier than the export/import method.


You mentioned the "trick" to show the POP option. I've actually used this in the past, and have a note about it, so thanks for reminding me. I'm concerned that using this "trick" might inadvertently work-around Outlook's Modern Authentication method.


Has anyone using POP been successful with this delete then re-add account method? How will I know if it was successful? Do I have to wait until September 16 to know if I beat the system?


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Outlook email requires "Modern Authentication Methods", Need correct Mail Settings for POP

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