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Can't send emails with any regularity. Seriously aggravating.

Have a new iMac (macOSCatalina version 10.15.6). Sending emails became erratic early on. Changed password, checked server setting repeatedly, spent hours on phone with Apple support and Earthlink.

Occasionally (and it seems to e in the evenings) outgoing email will work......until it doesn't. Connection doctor says all is good. I am now getting this message: " Cannot send message using the server Earthlink"

"Verify that you have addressed this message correctly. Check your SMTP server settings in Mail preferences and verify any advanced settings with your system administrator

The server response was: Please configure your mail client to use authentication.

Select a different outgoing mail server from the list below or click Try Later to leave the message in your Outbox until it can be sent. " Any ideas? Thank you!

iMac 21.5″, OS X 10.11

Posted on Sep 8, 2020 12:20 PM

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3 replies

Sep 8, 2020 4:02 PM in response to BDAqua

After initially changing the password emails were sent easily.........for the remainder of that day. The information you've supplied is awesome. Right now, outgoing email is working. I see a few differences from emailsfix from what I'd been advised to do. If the problem pops back up tomorrow, I'll reset my account again following those instruction. Thanks!

Sep 8, 2020 4:13 PM in response to MCAKW

Good to hear, if problems return...


Open Keychain Access in Utilities, then either check the Password under that item, change it, or delete it and start over.


Enter the part after the @sign in the search bar.


You may have duplicate or more entries in Keychain Access.


If using a browser to login via WebMail works it's not Name or Password, but likely old passwords interfering.


There''ll be at least 2 entries, maybe more.


The trouble is that Mac Mail almost always chooses the old Passwords if you don't change or get rid of the old ones.

Can't send emails with any regularity. Seriously aggravating.

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