Login Issue with Yahoo Account in Outlook for Mac

Marie Ilyina-Adaeva 0 Reputation points
2025-12-08T12:18:20.53+00:00

I cannot log into my Yahoo email account using the Outlook app for Mac (macOS Tahoe, version 26.1 ). Every attempt fails with the specific error message: "Something went wrong. We could not sign you in. Try again from a different device."

The account works flawlessly everywhere else: Outlook for iOS, Outlook for Windows, and web browsers (Safari/Chrome). The problem is isolated to Outlook for Mac.

I have exhausted all standard troubleshooting steps:

Toggling Yahoo's "Third-party app password" on and off (tried both regular and app passwords).

Turned off and on 2FA.

Multiple attempts to re-add the account from scratch.

Verified that my credentials are correct (I can log in via the web).

Also it seems that Outlook doesn't connect to Yahoo servers at all, because I tried to enter wrong password just to check if it will say "wrong password", but nothing changed, it showed the same "try again from different device" error message.

This persistent failure, coupled with the unhelpful error message, makes the app unusable for me.

Outlook | MacOS | New Outlook for Mac | For home

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  1. AI answer

    2025-12-08T12:18:33.5266667+00:00

    It seems you are experiencing a login issue with your Yahoo account specifically in Outlook for Mac. Since you've already tried various troubleshooting steps, here are a few additional suggestions that might help resolve the issue:

    1. Check for Updates: Ensure that your Outlook for Mac is updated to the latest version. Sometimes, login issues can be resolved with the latest updates that include bug fixes.
    2. Remove Cached Credentials: Sometimes, cached credentials can cause issues. You can try removing any saved Yahoo credentials from the Keychain Access on your Mac:
      • Quit Outlook and all other Office applications.
      • Open Keychain Access from Utilities.
      • Search for any entries related to Yahoo and delete them.
      • Restart Outlook and try logging in again.
    3. Check Account Settings: Double-check the account settings in Outlook for Mac to ensure they match the recommended settings for Yahoo accounts. This includes the incoming and outgoing server settings.
    4. Disable Add-ins: If you have any add-ins enabled in Outlook, try disabling them to see if they are causing the issue.
    5. Firewall and Security Software: Ensure that your firewall or any security software is not blocking Outlook from connecting to Yahoo servers.

    If these steps do not resolve the issue, you may want to consider reaching out to Microsoft support for further assistance, as they can provide more specific troubleshooting tailored to Outlook for Mac.

    References:

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  2. Jhun Buala 5,535 Reputation points Independent Advisor
    2025-12-08T14:02:53.8866667+00:00

    Hi Marie Ilyina-Adaeva,

    Good day. I'm Jhun an independent advisor. In regards with your login issue, try to do these additional options and see what will fix the problem.

    A. Reset Outlook's credential cache. Outlook often keeps a stale token for yahoo in MacOs keychain, clocking all new logins.

    1. Open Keychain Access.
    2. Search for: yahoo imap.mail.yahoo.com smtp.mail.yahoo.com outlook Microsoft Office Identities
    3. Delete ALL related entries.
    4. Restart your Mac.
    5. Try adding the Yahoo account again.

    B. Force Outlook to use IMAP instead of Oauth. Outlook 26.x sometimes fails Yahoo OAuth login handoff on macOS Tahoe.

    1. Try adding account > IMAP (not Yahoo button).
    2. Incoming server:
      imap.mail.yahoo.com Port: 993 SSL: On
    3. Outgoing server:
      smtp.mail.yahoo.com Port: 465 (or 587) SSL: On
    4. Use your Yahoo App Password and not your normal password. If manual IMAP succeeds, the issue is with Yahoo's OAuth redirect on MacOS.

    C. Disable Outlook’s “New Outlook” interface. The new Outlook for Mac sometimes breaks third-party OAuth logins. Switch back to Classic Outlook.

    1. Open Outlook.
    2. In the upper-right toggle off New Outlook.
    3. Restart Outlook.
    4. Add the account again.

    D. Fully Reset Outlook Profile. It may be corrupted.

    1. Close Outlook.
    2. Go to: ~/Library/Group Containers/UBF8T346G9.Office/Outlook
    3. Rename the folder Outlook to something like OutlookBackup.
    4. Reopen Outlook >it will create a fresh profile.
    5. Try adding Yahoo again.

    E. Check for MacOS tahoe webkit OAuth bug. macOS Tahoe (14.x equivalent) had a known bug where Outlook could not complete web-based logins for some providers.

    1. Go to System Settings > Privacy & Security > Profiles.
    2. Remove any leftover WebKit authentication profiles if they exist.
    3. Reboot.

    F. Reset Outlook identity tokens. This will force Outlook to regenerate OAuth related libraries.

    1. Quit Outlook.
    2. Remove this folder: ~/Library/Containers/com.microsoft.Outlook/Data/Library/Caches
    3. Reopen Outlook and try again.

    G. Confirm Safari Webkit is not blocking Oauth. Yahoo login is performed through an embedded Safari engine.

    1. Check Safari > Settings > Privacy.
    2. Turn off:
      Prevent cross-site tracking Block all cookies
    3. Retry adding the account. You can turn these back after.

    H. Remove any Yahoo account connected in MacOs internet accounts. Even if you're not actively using Apple Mail, an outdated token in macOS can break Outlook OAuth.

    1. Check, System Settings > Internet Accounts
    2. If Yahoo is listed > delete it
    3. Re-add only inside Outlook.

    I. Try adding through Outlook Web preferences sync. Sometimes Outlook Mac pulls settings from your Exchange profile online.

    1. Go to https://outlook.com > Settings > Sync email.
    2. Remove then re-add Yahoo here.
    3. Then try Outlook for Mac again.

    J. As a last option incase everything fails, do a clean reinstallation of Office.

    I hope this helps.

    Regards,
    Jhun

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