SSL connections and inconsistent mail sending

Hi guys,
This is a strange one...
I am using a MBP and a PB 12" from home both up to date with 10.5.3, .mac and mail.app
For the past month or so I have been having difficulties sending emails from my .mac account to a particular domain using mail.app. I get all the indications that the mail has been sent successfully (in the sent items, avaliable in sent items on web and iphone) but the message is never received by the recipients.
If I send an email from the webmail of .mac it is received fine.
If I send an email from my iphone using WiFi (same connection as the MBP) it works fine.
If I configure thunderbird (on the same computer) with no SSL to send from my .mac email account the email is received fine.
If I send an email using mail.app with my .mac email account, on either computer, it is NEVER received.
I thought originally it might be my network at home so I went to a starbucks and tried using their network and I had the same problem...
I have tried creating a new user account and setting up mail.app from scratch and still I have the same problem.
I'm running out of ideas and need some help from the pro's.
Has anyone got any ideas of what is going wrong?
Thanks in advance,
mjharps

Upgraded to 10.5.4 and it solved the problem!

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