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troubleshooting Question

E-Mail sent from Hotmail.com never arrives to server - is it forever lost in the aether?

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Kumba42Flag for United States of America asked on
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18 Comments1 Solution1308 ViewsLast Modified:
So I just deployed a new Exchange 2007 server, and largely, things have gone smoothly.  Barring having to finally upgrade internal clients to Office 2003 (we're poor), the only major issue plaguing my new server is, ironically enough, Hotmail.  It seems some high profile people involved with my organization use Hotmail as their main form of e-mail, and their messages, plus several of my own from my own hotmail account, seemingly disappear into the Internet equivalent of /dev/null.

I did several test messages from my own Hotmail account, ranging from a one-line "this is a test" message to 17 paragraphs of generated Latin (from the Lorem Ipsum generator).  One message was even about three, basic English sentences I wrote.  Not a single one made it to my Exchange mailbox.  No traces in Message Tracking, in the Queues, etc.  No bounce back or rejection messages are sent to my Hotmail account.  Nada, Zilch, None.

Obviously, this does not help me at all.  I think it may be my spam filtering on my new server, so I've already done several things like crank the Content Filtering threshold up to its maximum value so that only the most spam of spam gets tagged and rejected.  I then went a step further, and redirected all spam with an SCL of 9 to a special mailbox I'm monitoring.  None so far are sent from or to Hotmail accounts.

I also tweaked some of the other values, but messages from my Hotmail account still don't arrive.  So I'm really at a loss on what else to do.  Without any kind of diagnostic information, I have no way of knowing where the fault is at.  And Microsoft doesn't help things very much by providing an easy-to-find contact address/form for Hotmail to get their help on this (And I'd be surprised if they'd even help at all).

So my question is this: Where are my messages going, how can I find them, and how can I make my server accept Hotmail.  Some reading states that Wildcard whitelisting was broken by a patch in Exchange 2007 SP1, which is just really fantastic.  That rules that option out for whitelisting the entire *@hotmail domain just in case it's something like my RBL doing this.  So I figure there's got to be other ways to resolve this.
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