My iCloud mail in MS Office 365 Outlook is no longer updating

Question

I read and respond to my iCloud emails in MS Office 365 Outlook on my home Mac computer. Starting yesterday, I can see all my e-mails up to a certain time, but after that time I was unable to receive or respond to any subsequent e-mails. (The Outlook app on my iPhone, however, is working--receiving e-mails, etc.) There is a red circle, with an exclamation point inside it, next to my iCloud e-mail account in Outlook. When I click on it, it says "Something went wrong. Please sign in again for this account" with a Sign In link. When I click to sign in, a box appears that says, "We need to launch a browser so you can sign in to (my iCloud e-mail account address)" with another Sign In link. When I click on that, it goes to appleid.apple.com, which says, "Sign in to your Apple Account to share account information with Microsoft Outlook apps and services" with the option to sign in with a password or passkey. I have a legitimate sign in email and password and they are good, but no matter what I do, they are not accepted. I have also clicked on "Forgot password?" and I can change my password but that doesn't work either. I went on Apple Support and chatted with a tech for almost an hour, and she finally said that my Apple/iCloud account is good and that the problem would have to be presented to Apple App support. I tried that, but nothing, so I can only guess the problem is now on the Microsoft side of things. I also know about needing app specific passwords and have tried that. I don't know what to do next. Any ideas would be appreciated. Thank you.

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Moved from: Microsoft 365 and Office | Access | For home | Other

Answer 1

Hi,

I’m really sorry about the issue you’re running into. Here are additional steps you can take to resolve your iCloud mail issue in Outlook on your Mac.

1. Delete Cached Passwords in Keychain Access

Corrupted or outdated cached credentials in your Mac's Keychain can interfere with Outlook's ability to authenticate.

• Quit Outlook and all other Microsoft Office applications.
• Open Keychain Access: Go to Finder > Applications > Utilities > Keychain Access.
• In the search field in the top right, type Exchange and delete all entries that relate to your iCloud or Microsoft 365 accounts.
• Repeat the process, searching for adal and deleting any related modern authentication tokens.
• Search for Office and delete any entries that seem relevant to your account or general Office credentials.
• Restart your Mac and then re-open Outlook to see if the authentication prompt works correctly with your app-specific password. 

2. Manually type the app-specific password (avoid copy-paste) 

Though counterintuitive, sometimes hidden characters get copied with the password when pasting, causing the authentication to fail. 

• Generate a new app-specific password on the appleid.apple.com website.
• When prompted for the password in Outlook, manually type the 16-character password (e.g., xxxx-xxxx-xxxx-xxxx) without the dashes, if Outlook allows, or precisely as displayed. 

3. Ensure macOS is up to date 

Compatibility issues can arise from an outdated operating system. 

• Click the Apple menu > System Settings > General > Software Update.
• Install any available macOS updates. 

4. Check "New Outlook" mode compatibility

Microsoft has a "New Outlook" experience which may handle iCloud authentication differently (sometimes better, with native support for the new authentication methods). 

• Check if you are using "New Outlook" or "Classic Outlook". In New Outlook for Mac, the setup process is more streamlined and might resolve the issue.
• If you're in the Classic view and the above steps fail, you may consider switching to New Outlook to leverage the improved authentication protocol.

5. Completely reinstall Office 365

As a final measure, a clean reinstall ensures no corrupted application files are causing the issue.

• Quit all Office applications.
• Move the Outlook app from the Applications folder to the Trash.
• Empty the Trash.
• Download and install the latest version of Office from your Microsoft account or the App Store.
• Set up your iCloud account again using a new app-specific password

You can also check on this link for more information:

Outlook 2016 for Mac repeatedly prompts for authentication

Hope that this information helps.

Kind regards,

Answer 2

It sounds like you're experiencing connectivity issues with your iCloud email in Microsoft Outlook for Mac. Here are some steps you can take to troubleshoot the problem:

1. Check Your Internet Connection: Ensure that your Mac is connected to the internet and that there are no network issues.
2. Update Outlook: Make sure that your Outlook application is up to date. Sometimes, outdated software can cause connectivity problems.
3. Re-enter Your iCloud Account: Since you're getting a prompt to sign in again, try removing your iCloud account from Outlook and then re-adding it. To do this:
   • Open Outlook and go to Tools > Accounts.
   • Select your iCloud account and click the minus (-) sign to remove it.
   • Then, click the plus (+) sign to add it back as an Other E-mail account, entering your email address and password.
4. Check for App-Specific Passwords: If you have two-factor authentication enabled on your Apple ID, ensure that you are using an app-specific password for Outlook. You can generate this from your Apple ID account settings.
5. Run Microsoft Diagnostics: If the issue persists, consider running the Microsoft 365 Diagnostic tool to identify and fix connectivity issues.
6. Contact Support: If none of these steps resolve the issue, you may need to contact Microsoft support for further assistance, as the problem could be on their end.

Following these steps should help you troubleshoot the issue with your iCloud email in Outlook.