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Hi!
I know it's been three years that you answered this question, but it only happened to me a couple of weeks ago.
Even before I found your post I had done everything you described and I still can't send messages through Live Mail.
My accounts were set as POP and were working fine. All of a sudden, I couldn't send or receive any message. After calling my ISP, they informed that they were offering the access through IMAP for some time now. That was weird
because my e-mail client was working fine the day before.
After several attempts on the account settings, I finally deleted one of my accounts and re-created it as a IMAP type. Now I can receive messages but I still can't send them. I verified the settings on my Avast firewall and all
the ports were allowed as well as on Windows Firewall.
I also used the repair tool from Windows on the Windows Essentials, but it solved nothing.
The same thing happened to my Outlook (2010) accounts, with the added problem that when I deleted one of the accounts, I couldn't add it again because of the impossibility of sending messages.
On the Outlook I also have a Gmail account configured and it works fine.
The error message I get on Live Mail is:
An unknown error has occurred.
Subject 'Teste'
Server Error: 421
Server Response: 421 Cannot establish SSL with SMTP server 208.84.244.140:465, SSL_connect error 5:connection closed
Server: 'smtp.terra.com.br'
Windows Live Mail Error ID: 0x800CCC67
Protocol: SMTP
Port: 587
Secure(SSL): No
...which is about the same as the one from Outlook. I also tried secure SSL and set the encryption to TSL - as it appears on the Gmail settings, but nothing works.
Thank you for any help.
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