One user getting You do not have permission to send to this recipient. Error

I have a company with about 50 users. One user keeps getting You do not have permission to send to this recipient.errors for some addresses he tries to send to. This has come up with now just gmail and hotmail addresses but business addresses as well.

But it's not with all addresses. For example he can email me and my email ends @iowaelectronics.com. It seems like random addresses and is just for this user. I can log in as administrator on his station as well and send email to these addresses.



not reach some or all of the intended recipients.

      Subject:    RE: [XXXXXXXXXXXXXXX New Email
      Sent: 9/17/2010 8:45 AM

The following recipient(s) cannot be reached:

      XXXXX@gmail.com on 9/17/2010 8:45 AM
            You do not have permission to send to this recipient.  For assistance, contact your system administrator.
            MSEXCH:MSExchangeIS:/DC=local/DC=domain-cr:MI2K3MS
message did not reach some or all of the intended recipients.

      Subject:    xxxxxx
      Sent: 9/20/2010 1:31 PM

The following recipient(s) cannot be reached:

     xxxxxxxxx@yahoo.com on 9/20/2010 1:31 PM
            You do not have permission to send to this recipient.  For assistance, contact your system administrator.
            MSEXCH:MSExchangeIS:/DC=local/DC=domain-cr:MI2K3MS

message did not reach some or all of the intended recipients.

      Subject:    xxxxxx!
      Sent: 9/20/2010 1:31 PM

The following recipient(s) cannot be reached:

     
Your message did not reach some or all of the intended recipients.

      Subject:    xxxxx
      Sent: 9/20/2010 1:36 PM

The following recipient(s) cannot be reached:

      xxxxx@hotmail.com on 9/20/2010 1:36 PM
            You do not have permission to send to this recipient.  For assistance, contact your system administrator.
            MSEXCH:MSExchangeIS:/DC=local/DC=domain-cr:MI2K3MS

LVL 2
Axis52401Security AnalystAsked:
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p_nutsConnect With a Mentor Commented:
it could be the send from address. if this user has multiple mailboxes and not send as rights on all.
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MalhovicCommented:
Close Outlook
Go through their computer to the following folder: %userprofile%\AppData\Local\Microsoft\Outlook and delete the extend.dat file.

Once that is complete, reopen outlook and see if this still happens. If so have him log into a different computer and test. Let me know if that is the case and requires further investigation.
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FDiskWizardCommented:
Is it actually going out to the Internet or just failing instantly?
If not going out, maybe it is anti-virus on Exchange? You aren't scanning your Database paths with a file-level antivirus are you?

Turn on message tracking, and do tracking on one of those...
Message tracking is enabled on the general tab of the server properties. (From ESM)

Then you can track via TOOLS > tracking in ESM.
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