Verification process to send mail fails

Question

Level 1

45 points

Verification process to send mail fails

I have a family member that can't send email. The verification process always fails. The username should be simply their first name but somewhere Mail.app keeps forcing it to be the first name plus the domain name.

So bob becomes *** which isn't the username an thus fails.

Since Apple added the automatically manage my mail settings check box. This has been a problem. That button only assumes emails are fully qualified such as ***

During initial configuration it is critically important to put the username as the last entry. If this isn't done then Mail.app replaces bob with ***. I have learned to always input the username last. If this isn't done the rest of the gui will display the correct username "bob" but this isn't what one will see in the mail server log file.

All login attempts will use *** instead of just bob. The entire account will need to be deleted and re-set up. This process has worked for at least 5 plus years.

Suddenly I have a user that no matter what I do the gui can't seem to convinced to use just the username.

If I use the connection doctor to confirm my settings everything passes the tests. If I try to send mail authentication fails. Connection doctor doesn't display the username during its tests so I'm not sure it is used to verify accounts.

I think it must be wrong inside the accounts.sqlite file...

Thanks,

Ben

[Edited by Moderator]

Posted on Nov 12, 2022 5:51 PM

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Answer 1

BDAqua

Level 10

239,777 points

Nov 13, 2022 8:17 AM in response to detourdog

See if any of these apply...

Mac's Mail App is not as modern as iOS's Mail app, Many eMail providers now require a separate App Password different from your eMail password…

Then you may need Ways to securely access AOL Mail…

https://help.aol.com/articles/allow-apps-that-use-less-secure-sign-in

Or it may just need an App Password separate from the gMail password…

https://support.google.com/mail/answer/185833?hl=en-GB

Apple Mail won't sign in to Google account - Apple Community

Note from PrestoWebDesign…

Trying to add Gmail account to Apple Mail… - Apple Community

Yahoo has gone to this too...

https://help.yahoo.com/kb/access-yahoo-mail-third-party-apps-sln15241.html

Yahoo App password…

Generate and manage third-party app passwords

Some older, third-party email apps (that do not use our Yahoo branded sign in page) require you to enter a single password for login credentials. To access your Yahoo Mail account on these apps, you'll need to generate and use an app password. An app password is a long, randomly generated code that gives a non-Yahoo app permission to access your Yahoo account. You’ll only need to provide this code once to sign in to your third-party email app.

https://help.yahoo.com/kb/access-yahoo-mail-third-party-apps-sln15241.html

Using app passwords with apps that don't support two-step verification (microsoft.com)

What about application passwords? Will that keep working?

If application passwords are being used for MFA (Multi Factor Authentication) along with basic auth as another auth mechanism, then when basic authentication is disabled, app passwords used for MFA will stop working too.

Where can I find more information?

There are several resources that we wanted to provide here as additional reading:

Basic Authentication Deprecation in Exchange Online – September 2022 Update – this is a comprehensive post containing more information about this effort.
Deprecation of Basic authentication in Exchange Online – our official documentation related to this effort, with links to much more information and guidance.

https://techcommunity.microsoft.com/t5/exchange-team-blog/exchange-online-email-applications-stopped-signing-in-or-keep/ba-p/3641943

Exchange Online email applications stopped signing in, or keep asking for passwords? Start here. - Microsoft Community Hub

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Answer 2

detourdog Author

Level 1

45 points

Nov 14, 2022 4:27 AM in response to BDAqua

I just wanted to close the issue saying that it wasn't the Mail.app at all. I believe it was a network/firewall issue.

Mail still assumes everyone's email address is the same as there username but it is easily worked around.

I wanted to also mention that my experience seem to point towards Connection Doctor in Mail only verifying that the mail server exists and is listening on known ports. The tool doesn't verify user credentials. Might be obvious but I thought pointing it out might add value to this thread.

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Answer 3

detourdog Author

Level 1

45 points

Nov 13, 2022 8:41 AM in response to BDAqua

Thank you for your response. I'm not sure if it really applies. This is my own mail server and I control the password policies. I could believe that it is becoming uncommon to use a login name as the username. I have working against this tide for probably 7 years. The workaround isn't working for this particular user.

Apple support had me upgrade to the latest version of High Sierra but that didn't help.

I would consider it being the MacBooks firewall but I can see in my mail server log that the laptop is passing the full email address instead of the username as a login.

I'm going to ignore this and assume it is the firewall. Maybe that will be the issue. I did try a new computer account on the same laptop which didn't fix it.

This happens to only effects the sending password on a particular MacBook.

I have standard process for creating accounts and it involves turning off all management functions and manually entering the email config. port 587 and md5-challenge response. The first screen for configuring an email account of other involves filling in a username, password, incoming server, and outgoing server.

If one fills out the fields in order Mail will revert the username field to Automatic each time the any other field is entered. One must be sure to fill out the username last before proceeding to the next screen.

Failure at this step sends the username to some location that no longer synchs with the GUI in my experience. This means that any email account editing of the username has no effect on the value sent to the server at this point. This has been true at least 7 years for me. The usually fix is to delete the account start from scratch and be careful as one proceeds. If I make to the next screen with the username unmodified I can manually fill my settings and everything works.

This work around is no longer working for only this case. Although I will be experimenting with different versions.

My daily driver is Ventura but it may have been upgrade migration rather then a new account added.

Thanks for your help,

Ben

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