outlook failing to send/receive to certain Hotmail addresses

[SamBrownlie]

At the place I work, we have recently set up Microsoft Exchange Server so we
can host our own e-mail addresses and websites. We've had nothing but trouble
since doing so - but that's another story! The problem I'm having at the
moment is that my Outlook seems to be failing to send/receive to certain
addresses.

We had someone say he'd e-mailed something through; this never arrived. I
probably would have assumed he simply misspelt the address or something of
the sort, except that I noticed we hadn't had many e-mails through at all
that day. So, wanting to be safe, I sent a test message from my personal
Hotmail account to the work e-mail I use. At that point, I had to leave for
an hour; when I got back, I checked the e-mail to see what was happening.

No e-mail came through from my Hotmail to Outlook. I tried sending from
Outlook to my Hotmail - nothing came through (Outlook, by the way, is set up
to use one of the work e-mail addresses which is hosted on our server). I
grabbed another staff member and got her to send some test e-mails, too. She
sent e-mails from a university e-mail account, her Hotmail, and a community
group e-mail account she has access to - all were sent to my work e-mail
address and all worked fine. Finally, she tried sending an e-mail from her
work address (some domain as the troublesome one) to my Hotmail - this failed
to send.

Does anyone have any suggestions as to what might be causing this?

 

[F. H. Muffman]

At the place I work, we have recently set up Microsoft Exchange Server so
we
can host our own e-mail addresses and websites. We've had nothing but
trouble
since doing so - but that's another story! The problem I'm having at the
moment is that my Outlook seems to be failing to send/receive to certain
addresses.

We had someone say he'd e-mailed something through; this never arrived. I
probably would have assumed he simply misspelt the address or something of
the sort, except that I noticed we hadn't had many e-mails through at all
that day. So, wanting to be safe, I sent a test message from my personal
Hotmail account to the work e-mail I use. At that point, I had to leave
for
an hour; when I got back, I checked the e-mail to see what was happening.

No e-mail came through from my Hotmail to Outlook. I tried sending from
Outlook to my Hotmail - nothing came through (Outlook, by the way, is set
up
to use one of the work e-mail addresses which is hosted on our server). I
grabbed another staff member and got her to send some test e-mails, too.
She
sent e-mails from a university e-mail account, her Hotmail, and a
community
group e-mail account she has access to - all were sent to my work e-mail
address and all worked fine. Finally, she tried sending an e-mail from her
work address (some domain as the troublesome one) to my Hotmail - this
failed
to send.

Does anyone have any suggestions as to what might be causing this?

Errrrr, well, I'm not sure I see where this is an Outlook issue.

I mean, does the email even make it to your server? Can you see it in OWA?
Outlook is just a mail client. You aren't mailing to it. You're mailing to
a server. If the mail gets to the server and doesn't get to the client,
then it's an Outlook issue.

If the Exchange Admin cranks up the SMTP logging, can they see the Hotmail
servers trying to submit a message to your server?

As for the other direction, again, server logs are most important, as is
trying from OWA. Get Outlook out of the picture, make sure that the server
is working right. If it is, build a new profile and only have it connect to
Exchange and see what happens then.