Scott,
     To be honest, a lot of what your asking is a little beyond me.  I have my 
Gmail account setup, and I'm assuming it was done right, as most of my messages 
are getting sent out.  So far, all I know is that the message is being 
registered as being sent out, as the e-mail is moved to the sent folder.  The 
mail program also makes the nifty airplane noise to indicate that the message 
is on its way out.  I've tried sending messages from 2 different networks, one  
in New York and one in Virginia,  and have gotten the same result.  After 
reading some of the experiences that others have had, I'm going to go ahead and 
send messages from the actual Gmail website as that doesn't cause any issues.

Thanks so much for the response and for the info.

Justin
On Sep 4, 2010, at 11:50 AM, Scott Granados wrote:

> Sure, what is the address top level domain you're sending from.
> 
> Is this your own mail server, do the reverse and forward records in DNS match?
> 
> Is there a PTR record present for your mail server if it's your own?
> 
> One possibility is that the mail server your writing from isn't properly 
> configured and or set up correctly in DNS and the target mail server where 
> your writing to is configured to reject mail thinking it's a spam source and 
> it may not allow the message to transfer at all.  It's part of the standard 
> ruleset in sendmail.
> 
> Are you certain your mail server is picking up the message, the message moves 
> from the outbox to the sent folder?
> 
> Give us a little background on your source address / mail server and maybe we 
> can provide somep ointers.
> 
> Just an idea I could be way off, it could be a mail program issue but that 
> seems like likely.  I am very very new to Apple mail though so take what I 
> say with a grain of sault.  I've been working on mail transfer agents for a 
> solid 20 years though so I've seen this type of behavior with misconfigured 
> mail servers.
> 
> Thanks
> Scott
> 
> On Sep 3, 2010, at 9:47 PM, Justin Kauflin wrote:
> 
>> Hey,
>> I've been experiencing a strange issue when using Apple Mail to send 
>> messages.  I've been sending them with no problems that I knew of until I 
>> sent some messages to a new address I hadn't sent to before.  According to 
>> Mail, the message was sent, but was never received by the person I sent it 
>> to.  I asked him to check the spam folder as well, but he had no luck 
>> finding it there either.  When I sent him the same message from GMail.com, 
>> he got it.  I'm a little worried about this, cause I don't know how many 
>> other times this has occurred.
>>    Does anyone have any ideas on why this might be happening?
>> 
>> Thanks,
>> Justin
>> 
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