Mail reluctant to send after having selected 'Use SSL' in server settings

I read yesterday afternoon on the security tips page [http://discussions.apple.com/thread.jspa?threadID=121760] the recommendation to ensure SSL is used for sending email. When I discovered the option to use SSL was not selected on the settings panel for my outgoing server, I selected it. But now, each time I attempt to send an email, Mail immediately tells me that it can't send using that server, and presents me with other choices. When I insist on using that server, it will try again and, most times, will then be successful... but sometimes several attempts are needed before the mail is sent.
Is there something I can do to avoid having to re-try each time I send an email?
Thanks!

is the port setting you mentioned on my end or theirs?
Well, it's on their end, but you must match whatever they set it to, sending Mail could be... ports 25, 587 and 465. Port 587 has to be SSL, and port 465 is enforced TLS-wrapped and is generally used by Outlook users.
Receiving Mail...
IMAP is port 143
IMAP-SSL is port 993
POP is port 110
POP-SSL is port 995

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