Dear TJ Miha,
Welcome to Microsoft Community.
I understand your situation and your needs. This is due to the fact that Microsoft now requires a new authentication style to access accounts on Microsoft domains such as Outlook, Hotmail, Live, msn. All previous emails that used Basic Authentication to log in will no longer be available after 16/09/2024. Therefore, you can no longer use theIMAP or POP protocol for the public mailbox. You can only use the new authentication style and set the Exchange protocol by default. This is Microsoft's latest public announcement.
I wonder what version is your iOS and your mac system? Please note that your iOS system must be 16.0 or higher to allow your Hotmail connected to outlook.com.
If you use Apple Mail:
Apple Mail supports Modern Authentication by default when you setup the account as Outlook.com. If you use Apple Mail and you are seeing password prompts or connection errors, this is most likely happening because your account got configured as basic authentication. To mitigate the issue, remove the account and add it back as Outlook.com:
- Go to Settings > Mail > Accounts.
- Tap the email account you want to remove from your iPhone, then tap Delete Account. For more information, please go to Add and remove email accounts on iPhone.
Disclaimer: Microsoft provides no assurances and/or warranties, implied or otherwise, and is not responsible for the information you receive from the third-party linked sites or any support related to technology.
On iPhone, add your account back to Apple Mail:
- Go to Settings > Mail.
- Tap Accounts, then tap Add Account.
- In the Add Account dialog, choose Outlook.com.
If removing and re-adding the account does not address the issue, do the following:
- Remove the account again.
- Go to Settings > Safari, then tap Clear History and Website Data.
- Reboot your iPhone.
- Add the account back and proceed through the Outlook.com account sign in flow.
In Apple Mail on Mac, set up your account by clicking on "Microsoft Exchange", this will add your account to OAuth.
To summarize:
- If your Outlook is configured to connect to Outlook.com using POP or IMAP:
You may frequently be requested to enter a password to authenticate, therefore your account can't be uses normally. It is necessary to re-add your Outlook.com account using automatic account setup instead of using POP/IMAP and SMTP, after that, OAuth is added to your account.
- If your mail app doesn't support OAuth, use another one.
This is usually not a problem to worry about, as most major email apps, including Apple Mail, New Outlook, Thunderbird now allow new authentication methods. If you are using a mail app that doesn't support OAuth, you can download Outlook from MS store on Windows or App Store on your mobile phone.
Of course, if you're still having trouble adding your account in Apple Mail, you can also download the latest version of the Outlook app.
I hope my answer is helpful to you.
Please feel free to let me know if you have any further updates, thanks.
Best regards
Stan - MSFT | Microsoft Community Support Specialist