Mail server doesn't support legacy (outdated, insecure) connection encryption that your email client (Outlook) wants ( Recent SSL Encryption Bugs (like Heartbleed bug) require we discontinue outdated Encryption ciphers, protocols for your security. However your email client is not the latest stable, secure version and does-not support the latest secure Encryption ciphers, protocols! )
If in your email account Settings, wrong port number for the outgoing (SMTP) server is specified ( Ensure if using SSL/TLS on SMTP port is set to 465 or 587 else set SMTP port to 25 or 26 )
If in your email account Settings, wrong port number for the incoming (POP, IMAP) server is specified ( Ensure if using SSL/TLS on IMAP port is set to 993 or if using POP3 port is set to 995 else set IMAP port to 143 or POP port to 110 )
Resolution
Upgrade your Microsoft Outlook to latest stable, secure version or
Move to an alternate free Email Client like Thunderbird which supports the latest security protocols and
Recheck Email account settings ports
Else if all above cannot be done or fail then disable SSL/TLS Encryption in your email account Settings. Then try sending yourself a test e-mail message to make sure it works.
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