Sent email to certain addresses disappears

I suspect this is happening with others but I know for sure it is happening with one particular address. When I send email to my parent's email address which is an msn account from my .mac mail acct using mac mail, the message simply disappears. It shows as sent on my macbook but they never receive it. I have sent emails in the past without a problem and I can receive email from them without a problem. I sent a test email to my hotmail acct at the same time I sent one to their msn acct and mine made it but theirs did not. I checked their junk folder and it is not in there either.
Any ideas?

You are not alone. I'm having similar thing happen when I reply to certain emails, though it seems more random to me. Both the original email and the reply disappear. Nothing seems to be sent and I don't get anything in my Sent folder. If I run a Spotlight check for either one, they show up in the listing and I can open them in individual windows, but I cannot open them in the Mail viewer.
Another oddity is that the reply shows up multiple times in the Spotlight listing. Obviously the file exists somewhere in the computer, though I can't find where. I believe that if you shut-down your computer or perhaps just close Mail, these missing emails disappear for good! Not a good thing if you cannot rely on your mail program.

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