Request For Help Diagnosing Mail Problem

Hi All!
I hate to be pesky by posting a second question this week, but I am lost diagnosing a mail problem.

On my Mac Mail, I have several e-mail addresses. Three are sbcglobal.net (A Yahoo account), a couple are from my ISP (wowway.com) and two are gmail. The wowway and gmail work fine. The 3 sbcglobal started acting up today & I'm confused about the cause.

I sent two e-mails with a sbc address & they sent fine. I went to send a third less than a minute later and I got the error message that a secure connection could not be made to the server. It eventually timed out. I tried the other sbc accounts & they won't send either. Connection Doctor says they are offline, but I can't figure out how to make them online.

For diagnostics:
A) I tried the other NON sbc accounts. They sent fine.
B) I verified that I had the correct SBC settings for outgoing mail in each account.
C) I tried sending from the web application at sbc (which is Yahoo). It sent fine from the web.
D) I looked in Keychain. There were two entries for each sbc account. One had a password that was 4 years old. One was the current password. I deleted the old ones.

My Conclusion So Far:
Since mail will send when using the web mail application (logged in to Yahoo), I assume the outgoing server is OK at sbcglobal.
That makes me believe the problem is with my Mac Mail application.

I am lost as to what to do next. I've read to reset the Keychain, but I have no idea how that is done. I don't mind removing all passwords for everything & starting over, if that is what is required. I've also read to remove the mail account & start over. Will that delete all of my current messages? ( If I have to lose them, so be it.)

How is my diagnosis? Am I on the right track?
What do you all suggest I try next?

Thanks Very Much for helping with this frustrating situation!
Paul

The one thing you don't want to do is delete the account as that will likely remove all your email from it. Not sure I would even trust a backup to restore from in that case. So, once again, don't do it.

Try changing your password to the account but do it from the server side. Then go back to your mail account and reset the password and try again. I have had to do that before with my gmail account and it worked. Worth a try.

Also before I forget, leave the keychain alone as that can cause more problems than what you have now.

Did you try to restart you Mac?

Thanks Guys for helping out.
I've tried many re-starts. Sadly, with no good results.

I did what you suggested, Chscag, and changed the password from the server's web page. It worked for one message. Here's what I did:
After changing the password on line, I went to Mail & told it of the new password. I was able to send one message before the problem started again. So I repeated, this time restarting the computer between logging off the web page & opening Mail. Now no luck at all. Nothing would send. So, I restarted the computer and changed password on line, then on Mail. Still not sending. I don't know why I could send one time only & only after the first password change.

Crazy, huh?

I'm wondering now if the problem with your sbcglobal.net account is a security issue? Perhaps an expired certificate? The fact that you were able to send one message before the system shut you down makes sense if it has to do with security. Either that or it's Gremlins!

See if you can get in touch with someone from Yahoo customer support and ask about the security issue. I know that Yahoo has not been very helpful in the past, but you might get lucky this time.

Thanks Chscag.
I've tried for a couple of days to get a support number for Yahoo that works. No Luck. I wrote to a help address I found, but it got rejected as undeliverable. So, I guess Yahoo's not going to be helpful. Oddly, the have more than a dozen help hits showing how to set up the outgoing server. Each one has different port numbers and smtp.xx.yy wording.

For "Plan B" I changed the outgoing server on the Yahoo (sbcglobal) accounts to use one of my GMail accounts. It sends, but isn't a proper solution because if someone clicks 'Reply" it goes to the GMail inbox. (And shows the gmail address as the "from" address.)

Plan C is to put the server back to sbcglobal & let the send time out until the error message box pops up. Then if I click a different server, even GMail, the recipient's reply goes to the sbcglobal address and the sender is still the sbcglobal address. This isn't a great plan, either.

I suppose it's time to start changing e-mail addresses away from Sbcglobal.