This is what I usually see when sending to a user(or group) that has the 
"Require that all senders are authenticated" box checked.

-----Original Message-----
From: Mayo, Bill [mailto:bem...@pittcountync.gov]
Sent: Thursday, February 23, 2012 10:22 AM
To: MS-Exchange Admin Issues
Subject: RE: I feel like I'm missing something obvious

That sounds like there is a delivery restriction on the mailbox.  Have you 
checked Properties, Exchange General, Delivery Restrictions?

-----Original Message-----
From: Kurt Buff [mailto:kurt.b...@gmail.com]
Sent: Thursday, February 23, 2012 12:09 PM
To: MS-Exchange Admin Issues
Subject: Re: I feel like I'm missing something obvious

On Wed, Feb 22, 2012 at 18:58, Richard Stovall <rich...@gmail.com> wrote:
> Can you telnet directly to Exchange from inside your firewall and send
> a message to jd...@example.com manually?

Here's where it gets curious...

BTW, I used blat, cause it's easier, and made sure it came from my address, so 
any NDR would end up in my mailbox - and indeed I got one.

Below are the command line, output and full NDR. However, this is the most 
relevant output:
            You do not have permission to send to this recipient.  For 
assistance, contact your system administrator.
            <zxch.example.com #5.7.1>

Kurt

----------Begin Blat command----------
blat dummy.txt -subject "test from Kurt via blat" -to jd...@example.com -f 
kb...@example.com -server zxch.example.com -d -debug ----------End Blat 
command----------

----------Begin Blat conversation---------- Sending mac.txt to 
jd...@example.com Subject:test from Kurt via blat Login name is 
kb...@example.com <<<getline<<< 220 zxch.example.com Microsoft ESMTP MAIL 
Service,
Version: 6.0.3790.4675 ready at  Thu, 23 Feb 2012 08:57:47 -0800

>>>putline>>> EHLO IT-KBUFF

<<<getline<<< 250-zxch.example.com Hello [192.168.15.75] 250-TURN 250-SIZE 
250-ETRN 250-PIPELINING 250-DSN 250-ENHANCEDSTATUSCODES 250-8bitmime 
250-BINARYMIME 250-CHUNKING 250-VRFY 250-X-EXPS GSSAPI NTLM LOGIN 
250-X-EXPS=LOGIN 250-AUTH GSSAPI NTLM LOGIN 250-AUTH=LOGIN 250-X-LINK2STATE
250-XEXCH50
250 OK

>>>putline>>> MAIL From:<kb...@example.com>

<<<getline<<< 250 2.1.0 kb...@example.com....Sender OK

>>>putline>>> RCPT To: <jd...@example.com>

<<<getline<<< 250 2.1.5 jd...@example.com

>>>putline>>> DATA

<<<getline<<< 354 Start mail input; end with <CRLF>.<CRLF>

<<<getline<<< 250 2.6.0 <zxchlzz02h67yrlvbnd00000...@zxch.example.com>
Queued mail for delivery

>>>putline>>> QUIT

<<<getline<<< 221 2.0.0 zxch.example.com Service closing transmission channel 
----------End Blat conversation----------

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

      Subject:  test from Kurt via blat
      Sent:     2012-02-23 08:58

The following recipient(s) cannot be reached:

      Jeremy Diaz on 2012-02-23 08:58
            You do not have permission to send to this recipient.  For 
assistance, contact your system administrator.
            <zxch.example.com #5.7.1>
----------End NDR----------

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