Outlook 2010 - Strange email bounce back issue.

Hello,
   I have a user who's emails are getting rejected by some mail servers.  We are on Exchange 2007, and the user is using Outlook 2010.  The strange thing is, I and many other users on the same server can send to the same address no problem.
   I also found that if the user sends mail from OWA or his phone, it goes through fine as well.  His emails get blocked only when he sends from Outlook 2010 on his PC.  I thought it might be something with his ost file, so I had him
delete it and Outlook rebuilt it.  But the issue persisted.  His emails got rejected with a 554 denied error.
   I checked and our Exchange server is not on any blacklists and has a good reputation.  Its just this one user that is getting rejected when he sends mail to certain addresses from Outlook 2010.  Is there an issue with Outlook that
would cause something like this?
Thanks.

Hi,
According to your description, I understand that the issue only occurs when sending message from the Outlook client.
Please check the Blocked Senders and Safe Recipients settings in Junk E-mail Options in Outlook 2010. Also try to start Outlook in safe mode and send the test message to check whether the issue persists. If it doesn’t work, change a computer to have a try.
Regards,
Winnie Liang
TechNet Community Support

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    Hi,
    Since this is an Exchange forum and your issue is related to domain.live.com, I recommend you contact with domain.live.com support to get quicker and more professional help:<cite class="_Vc">https://domains.live.com/support/
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    Thanks for your understanding in advance.
    Best regards,
    Angela Shi
    TechNet Community Support

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