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

Outlook 2007 behind Exchange 2003 environment.  I have a user trying to send an email to someone on the same domain.  This user has two PC's, one desktop and one laptop, both on the domain.  From the users desktop he can send emails with no problem.  From the users laptop, when sending an email to ONE particular user he gets the following error:

Your message did not reach some or all of the intended recipients.
      Subject:  FW: Mortgage Message - (Loan Number: 293086406) - New Task Assigned
      Sent:     7/13/2009 9:28 AM
The following recipient(s) cannot be reached:
      recipient@acmecompany.com on 7/13/2009 9:28 AM
            The format of the e-mail address is incorrect.  Check the address, look up the recipient in the Address Book, or contact the recipient directly to find out the correct address.
            <acmecompany.com #5.1.3>

Again, it's isolated to his laptop - which confuses me.  Little help please?
sknoll84Asked:
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flyingskyCommented:
how did he put in the receipient's email address from his laptop? did he type in completely? pick up from address book? or just type a few character and auto-fill by the outlook?
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SaakarCommented:
What I belive from the NDR that you are getting is Exactly the same as flyingsky suggested to check, the local cache on the laptop is not picking up the correct email address, try creating a new profile in Outlook and check if you still the same error
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sknoll84Author Commented:
yeah he's typing in the address - I'll rebuild the profile as suggested.  
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Brian BEE Topic Advisor, Independant Technology ProfessionalCommented:
To be sure, the user should directly try to reply to a message they already got from that address rather than typing the address in manually.
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ArisglobalCommented:
Try to delete the .NK2 files to will remove the address cache on the Outlook Client
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sknoll84Author Commented:
the problem was with the address from within the .NK2 history

when emailing the user from the gal, everything went through okay. <firstlast@company.com>
when email the user from the autocomplete history, it bounced with the same nda. <Firstlast@company.com>

suprised that a capital letter threw everything off....
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ArisglobalCommented:
why B ? you didnt like the answer?
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sknoll84Author Commented:
because i solved it yesterday.....really never saw your post until after i resolved.
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SaakarCommented:
sknoll84, Well if you say that deleting the .NK2 file resolved the issue, I should say that my idea of recreating the profile would certainly do the same thing and the points should be assigned to me..
Let me know your thoughts about the same.
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sknoll84Author Commented:
you guys have to be kidding me...i never deleted the .NK2 history, that ruins peoples lives.
i never recreated the profile.  come to find out the email address was stored within autocomplete with a capital letter.  no suggestions were truly a resolution.  get over it.
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