[the_tyrant]

530 Must issue a STARTTLS command first - encryption required for requested authentication mechanism.

try this:

Open Windows Mail and click on Tools | Accounts

Select the name of your Hotmail account and click on Properties.

Click on the Servers tab and make sure the Incoming server
details contain your full Hotmail address and password.

Do NOT select the "Log on using Secure Password Authentication
(SPA) check box".

Under Outgoing Mail Server, check the box marked "My server
requires authentication".

Under Settings, select "Use same settings as my incoming mail
server".

Click on the Advanced tab.

The server port numbers should be 25 for Outgoing mail (SMTP) and
995 for Incoming mail (POP3).

Under both Outgoing mail (SMTP) and Incoming mail (POP3), select
the "This server requires a secure connection (SSL)" check boxes.

If you still cannot send emails with these settings, try changing
the port number for Outgoing Mail to 587 (instead of Port 25).