Version: 2008
Operating System: Mac OS X 10.6 (Snow Leopard)
Processor: Intel
Email Client: pop

I keep getting this error message on an almost daily basis when sending emails to people that that: <br><br>Have a legitimate Email Address <br><br>Are in my Entourage address book <br><br>I have exchanged emails with many times <br><br>I am using the same POP/SMTP server that I have always used.  The error will occur on a known user.  The solution is to delete the email address in the To field and then retype the email address - which of course fills it in from the address book AGAIN and then re-send. Most of the time the email will then be sent. <br>
A check of the previous postings indicates possible keychain errors but I don't see how that is viable given that the same keychain is being used for both emails.  <br>
This happens on an almost daily basis to almost any random email address in my address book.  I have tried deleting the email address and retyping it in the address book for some of the contacts but this does not seem to have any effect. <br>
I also use a Windows XP machine that uses Outlook and has the same usernames/email addresses in it and never get the error when sending to the same contacts.   <br>
Given the fact that the email can be sent successfully simply by deleting the address in the To field and re-typing it - which then fills it in from the address book - just like the first time the email was addressed - would seem to indicate that there is some problem with how Entourage addresses emails from the address book. <br>
A check of the error message shows the correct username and email address to the rejected user so it would seem that the problem occurs when Entourage attempts to actually do the send to the SMTP server. <br>
Hopefully someone knows the answer to this as I have checked for software updates multiple times and cannot find any and this is quite a time waster! <br>
Thanks for any assistance!