Justin, I have had this problem before and still do from time to time.  I have 
narrowed it down to something that may have nothing to do at all with Apple 
Mail, but here is how I live with the problem which I have thus far been unable 
to solve:

For several days, work colleagues were not getting my mail though I was sending 
it to them and nothing was ever bounced back.  It turned out in my case that 
when I changed my ISP, the headache went away.

I still have the same annoying problem with certain addresses whenever I use my 
mobile Internet broadband connection.  Strangely enough, I can't send messages 
to other people who are using the same Internet mobile broadband ISP.

I have never figured out the solution; I have just learned to live with it.  If 
I need to make good and sure that someone is going to get the message, I use 
the ISP's webmail interface to send the note.

Sorry I can't be of more help.

Mike


On 4,Sep,2010, at 3:47 AM, 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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