<p>This is a how to setup a secure (SSL) connection to your outlook.com account. It has been a bit of a PITA to get it working properly so I'll share my findings with you guys</p><p>First of all. IMAP doesn't work with outlook.com yet</p><p>POP3/SSL</p><p>Server HostName: pop3.live.com</p><p>UserName: [your email]@outlook.com</p><p>Password: [I hope you know this one]</p><p>TCP Port: 995</p><p>Security - Via Direct SSL connect</p><p>[X] Disable certificate validation (Shame on you Microsoft - Try WITH validation first in case MS fixed it)</p><p>SMTP/SSL</p><p>Server Host Name: smtp.live.com</p><p>TCP Port: 587</p><p>Security - Via STARTTLS</p><p> [X] Disable certificate validation (Shame on you Microsoft - Try WITH validation first in case MS fixed it) </p><p>[X] Login to the SMTP server using the following details - Same UserName and Password as POP3</p><p> </p><p>Enjoy semi safe emailing (Shame on you MS x3)</p><p>Oh I forgot - First attempt to send an email will fail. MS Will send you an automated email response with a validation link challenge.</p>