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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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