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Here's information on how to setup Outlook 2016 to work with Yahoo mail. You may need to generate an app password in order to get this to work. In order to do this you will need to activate either two-step verifcation or the feature Yahoo Account Key before you will see the option to do this.
Generate third-party app passwords - https://help.yahoo.com/kb/mail/learn-passwords-sln15241.html
If you are looking for the option to allow less secure sign in but aren't seeing it that would mean you have enabled either two-step verification or the feature called Yahoo Account Key. You will need to disable the feature you have enabled in order to see this option
I have had this problem on and off for years. It's definitely a Yahoo problem, probably down to a particular mail server behaving oddly. It goes away on its own in the end, but no amount of messing with yahoo or outlook settings will get rid of it. A ghost in the machine.
I found a YouTube video that explains the problem very simply and offers an easy way to fix the issue; all in less than 5 min.
*Link Removed - See the community guidelines for more information.*
The problem centers around the two-step verification security option. Watch the video and you will learn how to create a second password for the two-step verification. It worked for me on the first try.
And since the fix was linked to a solution outside of the Yahoo community, it was disabled. Nice.
Anyway, the name of the video is:
How to fix Outlook keeps on asking for username and password and can not connect to Yahoo; by Harish Bhathee.
It took me a long time to find this advice and I confirm that the method shown in the video does work. Thanks to Harish Bhathee.
In short it shows how to enable 2 step verification and generate a password specific to Outlook.
The solution is in plain sight in the Yahoo account security pages, but Yahoo Help was no help at all in finding it.
I deduce that Yahoo really do not want anyone to use MS Outlook to read and archive their Yahoo email.
They may get their wish - but not in the way they want!
I have 1 desktop, 1 laptop and 1 Windows Lumia phone and have Outlook and after a week or two, I used to get error messages (same as everyone in this thread) that I need to enter my user name and password and as Outlook saves all the passwords, so I still used to write them, but again and again, the same dialog box used to pop up asking me for the password. I tried all the methods on this site and all the sites I searched for on Google and Bing but in the end I used to delete my account from Outlook from all 3 devices and then add them back on. It used to work flawlessly for a week or two, then used to be the same, giving prompts for user name and password.
I came up with a solution or I should say - I stumbled upon it. Logged into my Yahoo mail from my browser, meaning to contact support, but got busy in some work and then after after completely logging in and doing nothing in my email inbox, I just shut the browser down and you know what, that error from the Outlook went away. So I guess the reason for this error is that Yahoo wants us to just log into their web interface after a while.
Its been working fine after that and all my Outlook inbox across devices work fine. So any of you get into this kind of an error, just go to your browser and log into your Yahoo mail - its that simple
I FOUND THE SOLUTIONS TO: If Outlook 2016 or earlier versions keeps asking for your password over and over AFTER you have added it repeatedly in your Account Settings, The problem is that you need to make a password verification in the Outgoing Server area because you have only been changiing or adding your password on the start page.
Here's all you need to do:
1. Go back to Account Settings. Click on the email address you want to change, then select Change from the menu just above where it has Repair, Change, etc. UNTICK the box that says "Automatically send Test Message Before Next" or something like that. (This change defaults back to yes when you exit.)
2. Retype your password like you've already done about 5 times.
2. Click on "More Settings."
3. Go to "Outgoing Server" tab. See where it says something like Use the Same Server as My Incoming. UNTICK that.
4. Then it will ask for your email address and password. Add those here.
5. Then go back to Account Settings|Change, and this time, do select the option to send the test email.
6. After that is successful, then go back into Account Settings|Change and now you can select Use the Same Server as My Incoming.
None of this will work if you don't have the following:
--JoAn in Oklahoma City