Sendmail and Hotmail or rather lack of it

I’ve run into a problem where hotmail seems to be the only email that I can not send any email too using sendmail (or postfix on a mirror test machine). (Fedora 7 system).

Has anyone else had the same problem and managed to find a fix for this issue. I’ve scoured the internet using Google and many people who run their own email server complain about this but I’ve found no pointers as to what to try next.

If anyone has any ideas it would certainly help me out a lot.


Hi Nigel,

The problem isn’t sendmail, it lies with Microsoft or specifically MSN. If you create your own account on hotmail, then send an email to your account processed by sendamil and reply to it, the hotmail account will receive it fine.

It was interesting to note that my TrendMicro spam filter rejected the hotmail test email as spam :wink:

What is strange is that for reading email when I’m away I use Squirrelmail. If I send an email to my hotmail account using SquirrelMail from work then it works, pops up in my hotmail in-box.

If I use SquirrelMail from my home machine it does not …

The other thing that mystifies me is that when I used SurgeMail as the email server then that too worked, but it was a pain to keep up to date as I had to have a full development system on my server,just for email. hence my move to sendmail and testing postfix.

Oh Well,


What’s in the mail log?


Thanks for looking at this for me.

Here’s the log file information.

Oct 10 17:20:35 mail sendmail[763]: l9ANKX24000761: to=<>, ctladdr=<> (502/502), delay=00:00:01, xdelay=00:00:01, mailer=esmtp, pri=150603, [], dsn=2.0.0, stat=Sent ( <> Queued mail for delivery)

Here’s the header details from Yahoo. The line in bold seems to be the only one that’s really different but when I send using squirrelmail it adds in some authentication lines, (hope that makes sense)but still only sends to hotmail from my work.

X-Apparently-To: via; Wed, 10 Oct 2007 16:21:00 -0700
X-Originating-IP: []
Authentication-Results:; domainkeys=neutral (no sig)
Received: from (EHLO (
by with SMTP; Wed, 10 Oct 2007 16:21:00 -0700
Received: from sweetdreams ( [])
by (8.14.1/8.14.1) with SMTP id l9ANKX24000761;
Wed, 10 Oct 2007 17:20:34 -0600
From: "Nigel Aves" <>
To: <>, <>
Subject: test for joe
Date: Wed, 10 Oct 2007 17:21:00 -0600
MIME-Version: 1.0
Content-Type: text/plain;
Content-Transfer-Encoding: 7bit
X-Priority: 3 (Normal)
X-MSMail-Priority: Normal
X-Mailer: Microsoft Outlook IMO, Build 9.0.2416 (9.0.2911.0)
X-MimeOLE: Produced By Microsoft MimeOLE V6.00.3790.4133
Importance: Normal

Once again,

many thanks for looking at this.

Nigel Aves

I have the same problem now.
I can send large messages to hotmail but not one or two line emails.
any input or help will be appreciated.