One Solution to Outlook Suddenly Can’t Connect to Server

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[Drcard:))]

I posted this here because I use Outlook as my email app, but this really applies to any email app that uses an IMAP ATT/Yahoo account. I post this error and solution for others that might experience this.

Setup: ATT email account setup thru Yahoo mail service with Outlook 2019 on Windows 10 home.

Situation:
The ATT IMAP account in Outlook has been setup with a secondary mail key and functioning perfectly for many years. Suddenly Outlook displays a connection error (Error: Cannot connect to server) and presents the box to enter the correct password to connect to the server. The error created on every attempt to connect to the server and Outlook could not download or send any emails. I could connect to the account on the Yahoo web page and thru my iPhone.

Solution:
Since this connection problem was in Outlook and not my iPhone or Web page, and is password related this pointed to a change in security for Outlook settings or a secondary mail key as the problem since iPhone and Web mail doesn’t use a secondary mail key.
I contacted ATT support (had to ask for a supervisor that knew what I was talking about). ATT had not made any “changes” to cause this, but he verified that my current secondary mail key no longer worked. Why? He said he didn’t know but it seems to happen with older accounts. Upon creating a new secondary mail key I noticed that the first secondary mail key I created was exactly to the day 3 years ago. How many think that is just a coincidence?
Solution was to create a new secondary mail key and connection was instantly restored.
So, does that mean that secondary mail keys have an expiration date? Appears that way for ATT/Yahoo. Haven’t had that problem with Gmail.

HTH, Dana:))

• This topic was modified 11 months, 2 weeks ago by Drcard:)).

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It’s normal for Outlook to pop-up that password box when there is a server connection issue.

For the first time in a long time I had this problem too with my Yahoo POP3 mail and Outlook 2019 starting Sunday afternoon (July 16). Although it did connect sometimes, but generally 90% of the time it failed. Yahoo mail worked fine with a web browser.

I didn’t do anything and everything was working flawlessly again the next day.

Wonder if changing the app password and it working was just a coincidence? I have the same app password ever since Yahoo required it for POP3 access.

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finkj wrote:

Wonder if changing the app password and it working was just a coincidence?

This is an IMAP account and even moving emails between the folders in Outlook caused the syncing of the folders to fail with the error message. It did this 5 times in testing just minutes before I generated and installed a secondary mail key (the primary password of many years has stayed the same during all this). The next time after entering the new generated secondary mail key it downloaded all emails and synced all folders. NO, I do not believe that changing the secondary mail key and it just starting to work is a coincidence. As I said the ATT service supervisor tested my then current secondary mail key and determined it was not working, but all other settings were correct.

HTH, Dana:))

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Dana,

First I’ve ever heard of a “secondary mail key”! Just how do you generate one?

May the Forces of good computing be with you!

RG

PowerShell & VBA Rule!
Computer Specs

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This has to do with OAuth/OAuth2 (or whatever security passcode generation they are using now). I have run in to this several years ago and here is a link to previous discussions and an explanation. There is (I think a different system now, but it works like Dana is saying.

https://www.askwoody.com/forums/search/OAuth/?gdpos=power-search-request&gdpos_search_users_input=PKCano

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RetiredGeek wrote:

Dana, First I’ve ever heard of a “secondary mail key”! Just how do you generate one?

That is what ATT calls their OAuth (your password for that email account is the first key and this app generated password is the second key). This is used for connections to an email app on a PC such as Outlook. The Web page or a smart phone doesn’t require it.
The secondary mail key is generated by an app of the mail service provider (in my case ATT). You go to the web page for the app. On the web page you will have to enter your email address (account) your email password (first key) you have for that email account. The app will generate a log difficult password which you copy. You even get to name this secondary key which is where I found my first secondary key and the date it was created. This long difficult to crack second key (password) that is connected to your first password is pasted into Outlook as “password” for this account to connect to server. Note: Entering the email account’s first password in Outlook will not work for OAuth connections which require the mail server’s app generated password to connect.

HTH, Dana:))

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RetiredGeek

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Dana,

Thanks, I remember doing this for GMail Accounts when I was using POP in Outlook (“Less Secure Devices” they called it.).

May the Forces of good computing be with you!

RG

PowerShell & VBA Rule!
Computer Specs

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