Mac 10.14.4 & Apple Mail 12.4 SMTP failure

Jason Johanknecht
Jason Johanknecht used Ask the Experts™
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Mac 10.14.4 with apple mail 12.4 and user can no longer send e-mail with DMARC failure response.  Client has Yahoo, Gmail, Centurytel, and iCloud e-mail accounts.  No account can send e-mail due to every account was trying to use GMAIL for SMTP.  Tried adding a iCloud SMTP server as Apple recommended, but once I select iCloud for SMTP on any account it quickly defaults back to None.  I have scanned to computer for viruses with Avast Free, as the computer had no protection and she had fallen victim to a tech support scam on this computer.
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David FavorFractional CTO
Distinguished Expert 2018

Commented:
You said, "but once I select iCloud for SMTP on any account it quickly defaults back to None" which suggests either your local permissions are incorrect or (more likely) the host/port/user/pass setup for iCloud SMTP is incorrect.

Test using http://www.jetmore.org/john/code/swaks/ first + post the full (text not image) output of SWAKS.

Syntax of your SWAKS test will be...

swaks -s icloud-host:587 -tls -auth -au $user -ap $pass --from=you@somewhere.com --to=test-address@somewhere.com

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Jason JohanknechtIT Manager

Author

Commented:
I have tried all of the accounts, reset the passwords, verified all of the settings.  I have tried auto settings and manual.  I will have access to the laptop again on Friday, and will try the SWAKS.  I am very used to Gmail settings in Windows programs, but the Apple Mail latest version is very different.  We rarely see any Macs in this area.  98% Windows users.
David FavorFractional CTO
Distinguished Expert 2018

Commented:
Mail debugging is always an adventure.

Give SWAKS a try + post (text not image) SWAKS output.

Likely SWAKS will show the exact problem + you can fix this instantly.
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David FavorFractional CTO
Distinguished Expert 2018

Commented:
One other thing to check.

Make sure port 587 is open on the Mac with the problem.

Port 587 is usually open by default + if it's closed mail submission will fail.

If this is the case, SWAKS will show it's unable to even start a transaction with Gmail, in the form of a connection failure.
In Mail.app, go to account preferences (Command , [comma]  - select accounts)  Select Server Settings and make sure each account has an  appropriate outgoing account server set.

You're supposed to be able to choose the outgoing account.  If it's always trying to contact the gmail servers, DKIM and SPIF tends to block you from connecting directly and sending spoofed content.
Jason JohanknechtIT Manager

Author

Commented:
The outgoing server is where it changes back to none.
David FavorFractional CTO
Distinguished Expert 2018

Commented:
Post output of running SWAKS, as many times looking at the entire SMTP conversation answers this type of question instantly.
Jason JohanknechtIT Manager

Author

Commented:
It is on the schedule for Friday still.  No access until then.
Jason JohanknechtIT Manager

Author

Commented:
SWAKS answer was blacklisted.  I have checked the client IP (Since all work has to currently be done at their site) and it was listed on a couple.  I will next be asking for removal of mac book to another location for further testing.
Jason JohanknechtIT Manager

Author

Commented:
Also today I can choose the Centurylink SMTP server (They are on Centurylink DSL).  All other SMTP options fail.

Sending on Centurylink SMTP is blocked (Blacklisted) IP according to Apple Mail.
IT Manager
Commented:
eMclient replaced Apple Mail is the solution for my client.  Thanks to all who helped, but Apple Mail is broken since the update.

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