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Rejected emails, wierd issue regarding Iphone

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@discussions.microsoft.com Todd

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Jul 16, 2007, 12:18:04 PM7/16/07
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Hi, having a weird outbound issue on our exchange server with an iphone user.
When they send email to a local address, it is fine as it is local, but if he
sends to a different domain, the email gets rejected. I did a tracking search
and located the emails, and the last entry shows why it bounces, but I dont
know what to do with it.



<PartnerServer>**************************************************************************************************</PartnerServer>

I had him change the outbound mail to use our linux smtp server, and it
appeared to have sent the email, but he will be unable to send email to
company boxes due to the .local extension, the SMTP server wouldnt know where
to send them.

Any ideas where to look?

Andy David {MVP}

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Jul 16, 2007, 2:09:05 PM7/16/07
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Cisco Firewall? Looks like SMTP fixup is enabled. Disable it.

Todd

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Jul 16, 2007, 2:18:02 PM7/16/07
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Why would the firewall be an issue just for the iphone user? All the rest of
the mail is going through OK. The sender is behind the firewall too.

Andy David {MVP}

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Jul 16, 2007, 3:07:56 PM7/16/07
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On Mon, 16 Jul 2007 11:18:02 -0700, Todd
<To...@discussions.microsoft.com> wrote:

>Why would the firewall be an issue just for the iphone user? All the rest of
>the mail is going through OK. The sender is behind the firewall too.

Just a guess of course.
Are you using Cisco?
The SMTP fixup stuff inserts itself into the conversation and
sometimes causes issues.

There be something there that it doesnt like.

Todd

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Jul 16, 2007, 4:46:02 PM7/16/07
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OK, this has me thinking a bit, I am not sure how his Iphone is routing to
the server, I think it is either on his local wireless net, or through our
VPN. If through the VPN it should never see the firewall as it is fully
behind it, but if he is using his local wireless net, there is a chance it is
routing over his cable modem and not the T1. That MAY put him through the
firewall, but I dont know if the iphone has traceroute.
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