Adding a Yahoo email account to Classic Outlook in Microsoft Office 365

Question

Adding a Yahoo email account to Classic Outlook in Microsoft Office 365

Jim Ford 40

Have new PC with Windows 11. Transferred material from old PC (Windows 8.1). There were 3 Yahoo email accounts in Outlook on old PC.

New Outlook set up seems to have worked for all 3 accounts [jxxxxxx*@yahoo.com, *****@yahoo.com and ******@yahoo.com]. The emails for all 3 accounts from the old PC Outlook are there.

However, in Classic Outlook, only 2 accounts will add [******@yahoo.com and ****@yahoo.com]. When I try to add the 3rd account [jxxxxxx@yahoo.com] (which is actually my main account) it will not add. Tried to do it Automatically by selecting "Connect" and also Manually by selecting "Advance Options" then going to the page where I select IMAP from the choices (Microsoft 365, Outlook.com, Exchange, Google, POP, IMAP, Exchange 2013 or earlier). I get a page for a Yahoo sign in where my Yahoo user name is filled in already. After I add my Yahoo sign in password I get this error Message: Sorry, we could not sign you in to YahooImap. Try again later

I have tried various steps on Microsoft Learn and Microsoft Support and Guided Support -but nothing seems to work.

NOTE: This may be part of the problem. And I do not know how it got there.

When I go to online Outlook [Outlook.com] I get a version of Outlook with this account [outlook_(various Letters and numbers)@outlook.com] and it has some of my old emails (before 2022) and if I click on File then Account then Manage I see information about my current subscription to Microsoft Office.

Something is wrong but I can't seem to find a way to correct it. It looks like the wrong account (an old account) is connected to my new subscription to Microsoft Office .

Who can I contact?

Why is this only affecting Classic Outlook?

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woodsy 0 Reputation points

2026-09-28T07:41:38.3466667+00:00

I have the same issue. Old laptop with Office 2016 and Outlook Classic works fine. New laptop trying to set up yahoo account and keeps getting an issue saying cannot connect to the incoming SMTP server. I have an app password generated for yahoo and also tried the original yahoo password; both fail. If I add as microsoft 365/outlook.com or exchange mailbox, it seems to progress into outlook without the error and the mailbox appears, but no emails download...
Hornblower409 16,075 Reputation points

2026-09-29T04:08:23.61+00:00

@woodsy said

New laptop trying to set up yahoo account and keeps getting an issue saying cannot connect to the incoming SMTP server. I have an app password generated for yahoo

You should not need an App Password to add a Yahoo account to either New or Classic Outlook. Outlook should "auto discovery" the correct server setting and use OAuth to authenticate.

Have you tried these instructions?
https://support.microsoft.com/en-us/outlook/getstarted/add-or-manage-a-yahoo-email-account-in-outlook

If this does not help, you need to start a new thread using the "Ask a question" button at the top of this page to create a new Question and include the details for your specific problem and what steps you have already tried to fix it.

This provides much higher visibility to your issue than adding on to an existing post, which is only seen by people who are already following this question.

2 answers

woodsy 0 Reputation points

2026-09-28T07:41:38.3466667+00:00

I have the same issue. Old laptop with Office 2016 and Outlook Classic works fine. New laptop trying to set up yahoo account and keeps getting an issue saying cannot connect to the incoming SMTP server. I have an app password generated for yahoo and also tried the original yahoo password; both fail. If I add as microsoft 365/outlook.com or exchange mailbox, it seems to progress into outlook without the error and the mailbox appears, but no emails download...
Hornblower409 16,075 Reputation points

2026-09-29T04:08:23.61+00:00

@woodsy said

New laptop trying to set up yahoo account and keeps getting an issue saying cannot connect to the incoming SMTP server. I have an app password generated for yahoo

You should not need an App Password to add a Yahoo account to either New or Classic Outlook. Outlook should "auto discovery" the correct server setting and use OAuth to authenticate.

Have you tried these instructions?
https://support.microsoft.com/en-us/outlook/getstarted/add-or-manage-a-yahoo-email-account-in-outlook

If this does not help, you need to start a new thread using the "Ask a question" button at the top of this page to create a new Question and include the details for your specific problem and what steps you have already tried to fix it.

This provides much higher visibility to your issue than adding on to an existing post, which is only seen by people who are already following this question.

Answer 1

Dear Jim Ford,

Thank you for posting your question to the Microsoft Q&A.

To connect with an application like Classic Outlook, many providers, including Yahoo, now require a specific 'app password' instead of your regular account password. This is likely why your main account is failing to add while the others work.

Please follow these steps to generate an app password and configure your account using the Control Panel method.

Part 1: Generate an App Password from the Yahoo Website

Open a web browser and go to the Yahoo login page.
Sign in with your Yahoo email address and your normal password.
Once logged in, click your profile icon and select Account Info (or Settings).
Navigate to the Security tab.
Under the 'Generate and manage app passwords' section, type "Outlook Desktop" as the name and click Generate.
The website will generate a unique long password code. Please copy this password to your clipboard.

Part 2: Add the Account to Outlook (via Control Panel)

Note: Since the "Add Account" button inside Outlook is getting stuck, we will use the Control Panel.

Close Outlook completely.
On your keyboard, press Windows Key + R, type control, and press Enter.
In Control Panel, click Mail (Microsoft Outlook) > Email Accounts > New.
Select Manual setup or additional server types > Next > POP or IMAP > Next.
Enter your ******@yahoo.com details manually.
Crucial Step: When prompted for the password, paste the App Password you generated from the Yahoo website. Do not use your regular Yahoo password.
Click More Settings to ensure your Outgoing Server requires authentication and your ports are set correctly (IMAP: 993, SMTP: 465), then click Next to finish.

Regarding the strange "outlook_[letters]" email address you saw, this occurs when a non-Microsoft email (like Yahoo) is your Primary Alias. It is a system label and does not affect your email functionality, therefore, you can safely ignore it.

I hope this explanation provides some clarity on what may have transpired. Please let me know how these suggestions work for you.

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

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Chloe-L 13,690 Reputation points Microsoft External Staff Moderator

2026-02-13T03:14:10.35+00:00

Dear Jim Ford,

Good day to you! I'm just checking in to see if the solution we provided has resolved your issue.

Please don't hesitate to reach out if you require any further assistance.

Warm regards,

Answer 2

It seems like you're experiencing issues with adding your Yahoo email account to Classic Outlook while it works in the new Outlook. Here are a few things to consider:

Account Configuration: Ensure that your Yahoo account is set up correctly for IMAP access. Yahoo requires that you enable "Allow apps that use less secure sign in" in your Yahoo account settings. This could be a reason for the sign-in error you're encountering.
Outlook Version: Since you mentioned that the new Outlook is working for all three accounts, it might be worth checking if there are any updates available for Classic Outlook. Sometimes, older versions may have compatibility issues with certain email providers.
Account Conflicts: The presence of an old Outlook.com account may be causing conflicts. Make sure that the Yahoo account you are trying to add does not have any existing settings or configurations that might interfere with the addition process.
Error Message: The error message you received, "Sorry, we could not sign you in to YahooImap. Try again later," can also indicate temporary issues with Yahoo's servers. It might be worth trying again after some time or checking Yahoo's service status.
Contact Support: If you've tried the above steps and are still having issues, it may be best to contact Microsoft Support for further assistance. They can provide more targeted help regarding your specific setup and account issues.

This problem seems to be specific to Classic Outlook, as the new Outlook is functioning correctly with your Yahoo accounts. It may be due to differences in how each version handles account authentication and settings.

References: