Problem with sending emails from within Mac Mail...

[Bob M.]

Hi all,

I'm using Earthlink to send/receive email within Mac Mail (the email program that comes with the iMac). I'm using OS High Sierra 10.13.6. The problem I'm having is I cannot send emails but receiving works fine. The unsent emails end up in my outbox and when I try to send them, I get a dialog box first prompting me for my email's account password. But then when I enter that it says: invalid name or password. I got a new password in April at the urging of Earthlink (they said my old one was too simple and asked me to change it to a longer, more hard to guess one) but the earthlink account and the mail program have worked fine since my password update (2 months ago) until about 4 days ago. At first, it would only refuse to send email to just a couple of people/companies, usually ones that I was emailing for the very first time and were not in my address book but then a day or so later, it stopped sending all emails. Initially, I was sending a test email to myself to another email account I have and that worked fine but then yesterday that also stopped working so I cannot send emails from this account at all.

Next, I called Earthlink customer service and spent about 40 minutes on the phone with a company representative whose primary language was not English and that was a bit difficult to communicate quickly and efficiently. I was able to confirm that the earthlink account password I've been using (the new one since April) is also the one they have on file for me.

I next went to the preferences in both Mail and at the Apple logo-> Internet Accounts and everything looked ok, to my untrained eye. Next I went to Keychain Access -> Passwords and I could only find 2 entry(s) that pertained to Earthlink. One was called IDS followed by my earthlink email address. I have no idea what this means or does. As I'm the administrator as well as the only user of this computer, I was able to read the password for this entry. It was 22 characters long and it was a password I've never seen or used before. The second entry said just earthlink and had a 7 character password that I've also never seen before. Now, in the past, I've has some trouble by going into Keychain Access and changing things around willy-nilly, usually more harm that good so I though I'd ask here first before leaping. I'm sure this has something to do with SMTP and out-going emails but I don't know where that information is stored for that or how to correct it.

Sorry for the long explanation but this problem seemed to warrant it.
What to do and try next?

Thanks in adv,
Bob M.

 

[IWT]

Hi Bob

Try this:

Open Mail > Mail Preferences > Click on Accounts and choose the "bad" one. In my case, I have chosen btinternet.com to illustrate what to do.

In the Incoming Mail Server replace the password with the correct one even if it is the same. Do the same for the Outgoing Mail Server.



Next: Click on Outgoing Mail Server, Click on the account, and choose Edit SMTP Server List



Again click on your account and input your Password even if it was the same as before.



Choose OK

Now the whole point of this exercise is to select the appropriate account and input the correct password in all the places as indicated in the screenshots.

Hopefully that should do it.

Please post back.

Ian

 

[krs]

If what Ian posted didn't resolve the issue, take a look and see what is selected in
Mail>Account>Server Settings "Automatically manage connection settings
both the incoming and outgoing mail server.

A while back I suddenly had a problem sending emails and after consulting with my ISP, deselecting this option for the Outgoing Mail Server only fixed my problem.

 

[IWT]

Great idea, krs. I've seen that mentioned on these Forums before. Well worth a try if the above failed to do the job.

Ian

 

[Bob M.]

Thanks... this idea worked !!

Hi IWT (Ian),

Yes, your instructions were perfect and the idea worked a charm. Essentially, it seems I'm just replacing the IMAP and SMTP passwords with my usual everyday password I use to log onto this email account (which may or may not have been one in the same). I guess I was under the impression that IMAP and SMTP each had their own unique passwords but that now seems erroneous.

I've sent a 'test' message to one of my other email accounts from this account and it works perfectly now.

I wonder what will I see in the Keychain Access for a password in my earthlink email address now that I've changed these passwords? And I wonder why this happened in the first place (computers aren't perfect).

Thanks again for the timely tutorial.

Bob M.

 

[IWT]

That's what we are here for, Bob. I'm so glad that things have worked out for you.

Ian

 

[Bob M.]

Yes, and thank you so much. It's refreshing that knowledgeable people like yourself take the time to help users with these 'low level' problems. Once again, I'm glad I logged on and asked.

Best regards,
Bob M.