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OS X Mail will not send messages after upgrading to 10.5 Leopard
Some customers have found that they are not able to send email after upgrading to Mac OS X 10.5 Leopard. The solution is to reconfigure the SMTP server(s) for email account(s) in Mail.app. Usually the SSL settings need to be toggled, and the port numbers reset to their proper values. Port number values depend on the email service provider. For example, if you use Gmail, and had it working properly in Mac OS X 10.4 Tiger, turn SSL off and back on again. Then set the port value to 587. Settings for different email providers may vary.
Launch mail.
Go to: "Mail menu > Preferences... > Accounts" and select "Edit Server List..." from the "Outgoing Mail Server (SMTP)..." drop down.
Click the "Advanced" tab and make changes there.