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Problem sending email to some domains

I am currently running exchange 2010.
I recently changed ISP. The new ISP did not configure reverse dns on the new IP when the change was made. Everything was working fine with email going out before I switch ISP. The ISP has since rectified the reverse dns issue. However when I tried to send email to some domains I am getting the following messages returned to my inbox:

1.)exchange.domain.com rejected your message to the following e-mail addresses:
user@domain.com
exchange.domain.com gave this error:
command unrecognised or out of order
A problem occurred during the delivery of this message to this e-mail address. Try sending this message again. If the problem continues, please contact your helpdesk.

Diagnostic information for administrators:
Generating server: exc_svr.domain.local
user@domain.com
exchange.domain.com #500 command unrecognised or out of order ##

2.) Delivery is delayed to these recipients or groups:
User Name (user@emaildomain.com)
Subject: Delivered: Re: update sfp record
This message hasn't been delivered yet. Delivery will continue to be attempted.
The server will keep trying to deliver this message for the next 1 days, 19 hours and 59 minutes. You'll be notified if the message can't be delivered by that time.

3.) When I tried to send email to hotmail I am also getting this message:

col0-mc4-f24.Col0.hotmail.com rejected your message to the following e-mail addresses:
username@hotmail.com (usename@hotmail.com)

col0-mc4-f24.Col0.hotmail.com gave this error:
SC-002 (COL0-MC4-F24) Unfortunately, messages from 84.126.35.44 weren't sent. Please contact your Internet service provider since part of their network is on our block list. You can also refer your provider to http://mail.live.com/mail/troubleshooting.aspx#errors.

A problem occurred during the delivery of this message to this e-mail address. Try sending this message again. If the problem continues, please contact your helpdesk.

i am sending fine to gmail and yahoo.
I could have sent email to hotmail and the other domains before. I haven't made any other changes on the network or exchane server.

I performed an outbound test using microsoft security analyzer with rdns, sender id check and black list check and all was successful including spf record.

I am getting frustrated over this. I don't know what else to try. Any help will be greatly appreciated.
 
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scopo
Asked:
scopo
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1 Solution
 
davealfordCommented:
Your IP address is on a blocklist. If your IP address is from a 'dynamic pool' asssignment then you'll need to send email through your ISPs SMTP relay or get the IP address removed from the dynamic pool (difficult). Even though you may have a 'static IP' it can still be in a dynamic pool.

Thing seem inconsistant as different recipients will be using diffrenet filters, some will block mail from dynamic pools, some don't, some use blocklists, some don't.

Get you IP address tested against a bloclist checker
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davealfordCommented:
If your IP address is 84.126.35.44 the it's listed on at least 4 blocklists -
Listed on 4 CASA-CBL+, CASA-CBL-, SORBS DNSBL, SPAMHAUS PBL2

The SORBS list is a list of dynamic pool assignments
SPAMHAUS PBL indicates ISPs IP addresses that shouldn't be sending email
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scopoAuthor Commented:
@ davealford: I am sorry but the IP listed is not my real ip. My real IP is 190.213.84.119. Is there a difference between blacklist and blocklist?

How can you tell if your static IP belong to a dynamic pool?
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davealfordCommented:
Blacklist / Blocklist really the same thing ....
Your IP isn't listed on the 54 lists I can check.
However, the Hotmail bounce message shows messages coming from 84.126.35.44 so, if you're not sending via your ISPs SMTP server are they 'proxying' you ie. they're grabbing all port 25 SMTP traffic and puching it through their SMTP server? In the UK, Freeserve (now part of Orange) did/still do do this).
Send an email to an address where you can view the headers and check what it's relaying through
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scopoAuthor Commented:
Ok Just so you understand I replaced my real ip with the made up ip of 84.126.35.44. I have no clue who's IP that is I just made it up. Sorry if that confused you.  However, going back and reviewing the exact message I think i realize what the problem. Hotmail is seeing a different IP than my mail server's IP. See below.

col0-mc4-f24.Col0.hotmail.com rejected your message to the following e-mail addresses:
scopo@hotmail.com (scopo@hotmail.com)

col0-mc4-f24.Col0.hotmail.com gave this error:
SC-002 (COL0-MC4-F24) Unfortunately, messages from 190.213.84.119 weren't sent. Please contact your Internet service provider since part of their network is on our block list. You can also refer your provider to http://mail.live.com/mail/troubleshooting.aspx#errors.

A problem occurred during the delivery of this message to this e-mail address. Try sending this message again. If the problem continues, please contact your helpdesk.


Diagnostic information for administrators:
Generating server: MAIR-EX.mair.local
scopo@hotmail.com
col0-mc4-f24.Col0.hotmail.com #550 SC-002 (COL0-MC4-F24) Unfortunately, messages from 190.213.84.119 weren't sent. Please contact your Internet service provider since part of their network is on our block list. You can also refer your provider to http://mail.live.com/mail/troubleshooting.aspx#errors. ##
Original message headers:
Received: from MAIR-EX.mair.local ([fe80::9d68:f57a:c6e5:8e89]) by
 MAIR-EX.mair.local ([fe80::9d68:f57a:c6e5:8e89%11]) with mapi id
 14.01.0289.001; Thu, 15 Sep 2011 05:58:50 -0400
From: System Support <system.support@mairandcompany.com>
To: "scopo@hotmail.com" <scopo@hotmail.com>
Subject: wet n
Thread-Topic: wet n
Thread-Index: AcxzjhGKZ+fUPY4CRmayFbMW+ZPV3g==
Date: Thu, 15 Sep 2011 09:58:50 +0000
Message-ID: <A46897D52F79D444A2CCC52B3FF10A339898B1@MAIR-EX.mair.local>
Accept-Language: en-GB, en-US
Content-Language: en-GB
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
x-originating-ip: [190.213.58.192]
Content-Type: multipart/alternative;
      boundary="_000_A46897D52F79D444A2CCC52B3FF10A339898B1MAIREXmairlocal_"
MIME-Version: 1.0
0
 
scopoAuthor Commented:
The originating IP would change depending on which computer you are sending the email from. So it still doesn't answer my question. That IP in bold happens to be my personal dynamic ISP at home IP.
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davealfordCommented:
The "x-originating-ip" is added by the server sending the message and would normally be the IP address being used by webmail etc. and is generally only used to trace who generated the original email.

The important bit is "Unfortunately, messages from 190.213.84.119 weren't sent." and, the bit after it - "Please contact your Internet service provider since part of their network is on our block "

Going to http://mail.live.com/mail/troubleshooting.aspx#errors.
Shows the error "550 SC-002" as  "Mail rejected by Windows Live Hotmail for policy reasons. The mail server IP connecting to Windows Live Hotmail has exhibited namespace mining behavior. If you are not an email/network admin please contact your Email/Internet Service Provider for help"

So, it looks like you may be (or, rather your server) trying to send email or are bouncing emails to non-existant hotmail addresses...... make sure you don't bounce undeliverable messages - you should reject them before they're delivered or send them to a black hole ...
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scopoAuthor Commented:
I am lost. When I send an email to my hotmail address from my domain email. It comes back immediately with the attached message. So I don't understand what you mean by bouncing emails as I get the message almost immediately. Does the part of the message you identified seem to suggest something with the current ISP? As I stated I had no issues with my previous ISP's IP.. And I could have sent email to hotmail and other domains without a problem. Thank you for your response so far "dave".
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scopoAuthor Commented:
Any update to this thread?
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scopoAuthor Commented:
I replaced the old connection and all mails going out without any problems. I conclude the problem is with the new ISP.
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scopoAuthor Commented:
I expected more participants on this thread.
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