Can't Generate 3rd Party App Password (AOL) for Outlook 2016 Desktop using Windows 11

I have a problem with my email account, after a few months I get a constant popup in outlook asking for username and password. I then have to get a new password and that system does not work. Support is telling me that you have to keep logging in every day until their system "trusts" your computer, then it will generate a password. Sounds like BS and the agent kept trying to sell me a monthly fee for a desktop app. I just want outlook to work.

Yup ... I noticed that when you get that constant popup in outlook asking for username and password, that means that you lost your connection to the AOL server. You need to generate a new password in order to reconnect. Been through that process many times! And like everyone else has commented ... AOL/Yahoo Customer Service is USELESS!!!

We should vote with our feet and leave AOL. there are other email providers out there that use Pop3 https://www.lifewire.com/top-free-pop3-and-imap-email-services-1171482

make sure you can log into the AOL web email. I am going to try ZOHO. slowly switch over companies that have ur Verizon email to ZOHO, then finally friends and family, keep monitoring ur verizon/aol email till the day you only get spam...then C'YA AOL. I had AOL dial up a long time ago then switched because of their shenanigans.

I called AOL's tech support and got someone that could barely speak English. They told me not to use an incognito browser. i asked what that was , knowing fully what it meant, they could not explain what it was and were just reading from a script. I tried signing into Edge but I am signed in as my hotmail account I clicked on add another account and i tried, it would not accept my AOL WEB password b/c it is off site, i would need the app password to create a new account in Edge, same for Chrome too.

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I too have run into this in the last couple of months. First started when I was helping my FIL make a transition back to Outlook from Windows Mail which wasn't working right with certain types of mail formating (HTML code would be displayed rather than the actual message for some types of mail). Anyway, went round and round and eventually got an AOL customer support rep to fess up about the issue once I countered his response that no one's having any issues with my findings that there are countless forum threads citing this issue as far back as October 2022 or longer. He then changed his tune and said that one needs to stay logged in or repeatedly log into the AOL web mail for consecutive days then the App Password Generator feature will become available and work. Said they had issue with security of the App Password Generator concept and that they were working on a fix. Well duh, of course you will have a problem using an app generator because if your primary AOL login password gets compromised and as a result change your password, if the process doesn't wipe the app passwords, whose to say that a rogue actor hasn't already generated a new unique app password they can use in a third party client to still have access to your email. and then if changing your main AOL password were to wipe the App passwords then you need to go back and generate news ones for whatever third party apps you are using. But the interim work around to generate an app password is not publicly communicated by AOL and thus everyone is left scratching their heads. I know they are trying to protect us but sometimes more harm is being done than good and especially when a poorly thought out idea gets implemented then retracted with little to know disclosure.

Well, I took his advice and left my FIL logged in to his AOL web mail for 2-3 days and then the App Password Generator started working and I was able to generate a password and configure his Outlook client. But I'm not sure the days logged in is a hard and fast rule because I just recently created a new aol.com email address because of problems I'm having with delivery of text messages to my verizon.net email address sent from my Verizon cellphone and VZ's recommendation that the issue might be because of the legacy verizon.net email address that is now an AOL/Yahoo mail provider. Anyway, turns out I have the same problem with text deliveries using the newaol.com address but when I went to generate an App Password for my new aol.com email address and after about 4 days, am still unable to generate one. I won't even get into the debacle with AOL about the text delivery issues which I can't get a straight answer from either VZ or AOL as to whose problem is it.

Maybe a class action lawsuit as they are preventing users from accessing their email using a third party app might wake them up.