IIS and SMTP - UNABLE TO SEND EMAIL TO HOTMAIL ADDRESSES

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Author UNABLE TO SEND EMAIL TO HOTMAIL ADDRESSES

2007-02-19, 7:19 am

I use Imail server and when i try to send emails to hotmail accounts im
getting an error. I can send email to other isp's email servers and Gmail
accounts without problem .

Hotmail error is

02:19 10:57 SMTP-(0AC002B3) 250-bay0-mc4-f22.bay0.hotmail.com (3.3.1.4)
Hello [88.247.85.148]
02:19 10:57 SMTP-(0AC002B3) 250-SIZE 29696000
02:19 10:57 SMTP-(0AC002B3) 250-PIPELINING
02:19 10:57 SMTP-(0AC002B3) 250-8bitmime
02:19 10:57 SMTP-(0AC002B3) 250-BINARYMIME
02:19 10:57 SMTP-(0AC002B3) 250-CHUNKING
02:19 10:57 SMTP-(0AC002B3) 250-AUTH LOGIN
02:19 10:57 SMTP-(0AC002B3) 250-AUTH=LOGIN
02:19 10:57 SMTP-(0AC002B3) 250 OK
02:19 10:57 SMTP-(0AC002B3) >MAIL FROM:<savas@alisverissaati.com>
02:19 10:57 SMTP-(0AC002B3) 550 Your e-mail was rejected for policy reasons
on this gateway. Reasons for rejection may be related to content such as
obscene language, graphics, or spam-like characteristics (or) other
reputation problems. For sender troubleshooting information, please go to
http://postmaster.msn.com. Please note: if you are an end-user please
contact your E-mail/Internet Service Provider for assistance.
02:19 10:57 SMTP-(0AC002B3) ERR undeliverable 550 Your e-mail was rejected
for policy reasons on this gateway. Reasons for rejection may be related to
content such as obscene language, graphics, or spam-like characteristics
(or) other reputation problems. For sender troubleshooting information,
02:19 10:57 SMTP-(0AC002B3) SMTP_DELIV_FAILED
02:19 10:57 SMTP-(0AC002B3) >QUIT
02:19 10:57 SMTP-(0AC002B3)
02:19 10:57 SMTP-(0AC002B3) Creating message from Postmaster


How can i fix it .. Im not blacklisted too..


PeterD

2007-02-19, 1:16 pm

On Mon, 19 Feb 2007 11:03:28 +0200, <in da club> wrote:

>I use Imail server and when i try to send emails to hotmail accounts im
>getting an error. I can send email to other isp's email servers and Gmail
>accounts without problem .
>
>Hotmail error is
>
>02:19 10:57 SMTP-(0AC002B3) 250-bay0-mc4-f22.bay0.hotmail.com (3.3.1.4)
>Hello [88.247.85.148]
>02:19 10:57 SMTP-(0AC002B3) 250-SIZE 29696000
>02:19 10:57 SMTP-(0AC002B3) 250-PIPELINING
>02:19 10:57 SMTP-(0AC002B3) 250-8bitmime
>02:19 10:57 SMTP-(0AC002B3) 250-BINARYMIME
>02:19 10:57 SMTP-(0AC002B3) 250-CHUNKING
>02:19 10:57 SMTP-(0AC002B3) 250-AUTH LOGIN
>02:19 10:57 SMTP-(0AC002B3) 250-AUTH=LOGIN
>02:19 10:57 SMTP-(0AC002B3) 250 OK
>02:19 10:57 SMTP-(0AC002B3) >MAIL FROM:<savas@alisverissaati.com>
>02:19 10:57 SMTP-(0AC002B3) 550 Your e-mail was rejected for policy reasons
>on this gateway. Reasons for rejection may be related to content such as
>obscene language, graphics, or spam-like characteristics (or) other
>reputation problems. For sender troubleshooting information, please go to
>http://postmaster.msn.com. Please note: if you are an end-user please
>contact your E-mail/Internet Service Provider for assistance.
>02:19 10:57 SMTP-(0AC002B3) ERR undeliverable 550 Your e-mail was rejected
>for policy reasons on this gateway. Reasons for rejection may be related to
>content such as obscene language, graphics, or spam-like characteristics
>(or) other reputation problems. For sender troubleshooting information,
>02:19 10:57 SMTP-(0AC002B3) SMTP_DELIV_FAILED
>02:19 10:57 SMTP-(0AC002B3) >QUIT
>02:19 10:57 SMTP-(0AC002B3)
>02:19 10:57 SMTP-(0AC002B3) Creating message from Postmaster
>
>
>How can i fix it .. Im not blacklisted too..
>


Did you do what the error message told you to do?

For sender troubleshooting information, please go to
http://postmaster.msn.com.

I'd guess you are on a dynamic IP or have a bad or missing RDNS
record.
Savas Ates

2007-02-19, 7:15 pm

Im sure I dont have dynamic IP. I use static ip which is 88.247.85.148
I have reverse dns too.
My domain name is
alisverissaati.com

195.214.184.130 ip has reverse dns record for alisverissaati.com..

88.247.85.148 ip has reverse dns record for indexinteractive.

The limitation is that one ip address can have only one reverse dns record
for a domain..

I visited http://postmaster.msn.com . They dont give any clue about my
issue. I also emailed microsoft support They havent reply yet.
Any help will be appreciated.








<in da club> wrote in message news:ufSG4SAVHHA.5100@TK2MSFTNGP06.phx.gbl...
>I use Imail server and when i try to send emails to hotmail accounts im
>getting an error. I can send email to other isp's email servers and Gmail
>accounts without problem .
>
> Hotmail error is
>
> 02:19 10:57 SMTP-(0AC002B3) 250-bay0-mc4-f22.bay0.hotmail.com (3.3.1.4)
> Hello [88.247.85.148]
> 02:19 10:57 SMTP-(0AC002B3) 250-SIZE 29696000
> 02:19 10:57 SMTP-(0AC002B3) 250-PIPELINING
> 02:19 10:57 SMTP-(0AC002B3) 250-8bitmime
> 02:19 10:57 SMTP-(0AC002B3) 250-BINARYMIME
> 02:19 10:57 SMTP-(0AC002B3) 250-CHUNKING
> 02:19 10:57 SMTP-(0AC002B3) 250-AUTH LOGIN
> 02:19 10:57 SMTP-(0AC002B3) 250-AUTH=LOGIN
> 02:19 10:57 SMTP-(0AC002B3) 250 OK
> 02:19 10:57 SMTP-(0AC002B3) >MAIL FROM:<savas@alisverissaati.com>
> 02:19 10:57 SMTP-(0AC002B3) 550 Your e-mail was rejected for policy
> reasons on this gateway. Reasons for rejection may be related to content
> such as obscene language, graphics, or spam-like characteristics (or)
> other reputation problems. For sender troubleshooting information, please
> go to http://postmaster.msn.com. Please note: if you are an end-user
> please contact your E-mail/Internet Service Provider for assistance.
> 02:19 10:57 SMTP-(0AC002B3) ERR undeliverable 550 Your e-mail was rejected
> for policy reasons on this gateway. Reasons for rejection may be related
> to content such as obscene language, graphics, or spam-like
> characteristics (or) other reputation problems. For sender troubleshooting
> information,
> 02:19 10:57 SMTP-(0AC002B3) SMTP_DELIV_FAILED
> 02:19 10:57 SMTP-(0AC002B3) >QUIT
> 02:19 10:57 SMTP-(0AC002B3)
> 02:19 10:57 SMTP-(0AC002B3) Creating message from Postmaster
>
>
> How can i fix it .. Im not blacklisted too..
>



PeterD

2007-02-19, 7:15 pm

On Mon, 19 Feb 2007 21:06:07 +0200, "Savas Ates" <in da club> wrote:

>Im sure I dont have dynamic IP. I use static ip which is 88.247.85.148
>I have reverse dns too.
>My domain name is
>alisverissaati.com
>
>195.214.184.130 ip has reverse dns record for alisverissaati.com..
>
>88.247.85.148 ip has reverse dns record for indexinteractive.
>
>The limitation is that one ip address can have only one reverse dns record
>for a domain..
>
>I visited http://postmaster.msn.com . They dont give any clue about my
>issue. I also emailed microsoft support They havent reply yet.
>Any help will be appreciated.
>


Make your reverse domain name equal to your domain name. They shoudl
not be different--email systems check and if they don't match, they
suspect the message is spam or worse.

The other IP address is???

You also seem to have major DNS issues, check the report at:

http://www.dnsreport.com/tools/dnsr...sverissaati.com

and correct these problems ASAP. For example, your domain A record
lists a local IP address.
Savas Ates

2007-02-19, 7:15 pm

88.247.85.148 ip address have some internal users and active directory in
our office. When i write a public ip for mx record (88.247.85.148) they are
not able to open mail.alisverissaati.com which serves as a web mail software
too.

How can i solve that problem ?


Savas Ates

2007-02-19, 7:15 pm

Those are the issues ...

my domain which is named alisverissaati.com

It has one mail server (88.247.85.148) and one web server(also has smtp
server to send email via web site) 195.214.184.128/29

I have my dns servers.

Both 88.247.85.148 and 195.214.184.128/29 (It is one machine.)
has Dns records for my domain.

My domain has Reverse Dns records and SPF records too.

88.247.85.148 has some internal users.


PeterD

2007-02-19, 7:15 pm

On Mon, 19 Feb 2007 22:58:28 +0200, "Savas Ates" <in da club> wrote:

>Those are the issues ...
>
>my domain which is named alisverissaati.com
>
>It has one mail server (88.247.85.148) and one web server(also has smtp
>server to send email via web site) 195.214.184.128/29
>
>I have my dns servers.
>
>Both 88.247.85.148 and 195.214.184.128/29 (It is one machine.)
>has Dns records for my domain.
>
>My domain has Reverse Dns records and SPF records too.
>
>88.247.85.148 has some internal users.
>


Go back and read my initial reply.

Go to the link and check your DNS report.

Fix the problems they find.

Specifically make your RDNS name the same as the DNS name.
NormanM

2007-02-19, 7:15 pm

On Mon, 19 Feb 2007 15:30:26 -0500, PeterD wrote:

> Make your reverse domain name equal to your domain name. They shoudl
> not be different--email systems check and if they don't match, they
> suspect the message is spam or worse.


According to which RFC? I just sent email into the 'msn.com' domain. Here is
the log entry:

| T 20070218 171217 45d8f820 Begin processing job MO000002 from %User_ID%@hupkid.us
| T 20070218 171359 45d8f820 Established ESMTP connection to 65.54.245.8
| T 20070218 173755 45d8f820 Connection closed normally.
| T 20070218 173755 45d8f820 Job MO000002 processing complete.

From a dynamic, residential account with rDNS in the 'pacbell.net' domain.
Here, I will send test email to two MSN Hotmail accounts I have:

| T 20070219 152844 45d8f822 Begin processing job MO000033 from %User_ID%@aosake.net
| T 20070219 153211 45d8f822 Established ESMTP connection to 65.54.244.136
| T 20070219 153212 45d8f822 MAIL FROM:<%User_ID%@aosake.net> SIZE=2211
| T 20070219 153212 45d8f822 250 %User_ID%@aosake.net....Sender OK
| T 20070219 153212 45d8f822 RCPT TO:<%User_ID#1%@hotmail.com>
| T 20070219 153212 45d8f822 250 %User_ID#1%@hotmail.com
| T 20070219 153212 45d8f822 RCPT TO:<%User_ID#2%@hotmail.com>
| T 20070219 153212 45d8f822 250 %User_ID#2%@hotmail.com
| T 20070219 153213 45d8f822 Connection closed normally.
| T 20070219 153213 45d8f822 Job MO000033 processing complete.

Here are the relevant lines for the accounts:

| X-Message-Info: txF49lGdW40+6b0VwzdVSOCnrB0/GlRdl1AQj15hsOs=
| Received: from aosake.net ([69.105.177.127]) by bay0-mc4-f7.bay0.hotmail.com with Microsoft SMTPSVC(6.0.3790.2444);
| Mon, 19 Feb 2007 15:32:26 -0800
| Received: from Spooler by aosake.net (Mercury/32 v4.01b) ID MO000033;
| 19 Feb 2007 15:32:12 -0800
| Received: from spooler by aosake.net (Mercury/32 v4.01b); 19 Feb 2007 15:28:33 -0800
| From: "Proper Name" <%User_ID%@aosake.net>

The same MSN server handled the message; same destination domain:
'hotmail.com'.

Now, an rDNS check on that sending IP address is interesting:

| 02/19/07 15:40:13 dns 69.105.177.127
| nslookup 69.105.177.127
| Canonical name: adsl-69-105-177-127.dsl.pltn13.pacbell.net
| Addresses:
| 69.105.177.127

So you tell me: If MSN is checking for a matchup between the sending domain
("EHLO aosake.net"), and the rDNS name of the connecting IP address
("adsl-69-105-177-127.dsl.pltn13.pacbell.net"), why did they accept these
email messages?

There is something else up. I do believe that MSN servers don't like
canonical aliases. The sending domain should either have an 'MX' record, or
an 'A' record. But that looks okay for the OP. It is hard for me to tell for
certain because everything he has is so convoluted.

--
Norman
~Oh Lord, why have you come
~To Konnyu, with the Lion and the Drum
NormanM

2007-02-20, 7:18 am

On Mon, 19 Feb 2007 11:03:28 +0200, in da club wrote:

> I use Imail server and when i try to send emails to hotmail accounts im
> getting an error. I can send email to other isp's email servers and Gmail
> accounts without problem .
>
> Hotmail error is


<snip>

> 02:19 10:57 SMTP-(0AC002B3) 550 Your e-mail was rejected for policy reasons
> on this gateway. Reasons for rejection may be related to content such as
> obscene language, graphics, or spam-like characteristics (or) other
> reputation problems. For sender troubleshooting information, please go to
> http://postmaster.msn.com. Please note: if you are an end-user please
> contact your E-mail/Internet Service Provider for assistance.


<snip>

> How can i fix it .. Im not blacklisted too..


Checking your domain name, 'alisverissaati.com':

http://www.dnsstuff.com/tools/looku...aati.com&type=A

Seems to be an 'A' record issue with that domain.

Checking your IP address, 88.247.85.148:

http://www.dnsstuff.com/tools/ptr.ch?ip=88.247.85.148

Points to 'indexinteractive.com', but there is no 'A' record, only a
'CNAME':

| 02/19/07 22:53:52 dns 88.247.85.148
| nslookup 88.247.85.148
| Canonical name: indexinteractive.com
| Addresses:
| 88.247.85.148

Checking your IP address, 195.214.184.130:

Points to 'mail.alisverissaati.com', but the 'A' record for
'mail.alisverissaati.com' points to 88.247.85.148. I believe it should point
to 195.214.184.130.

Using Sam Spade tools to dig on your domain name:

| 02/19/07 23:00:51 dig alisverissaati.com @ 68.94.156.1
| Dig alisverissaati.com@netsel failed, no such host
| Dig alisverissaati.com@68.94.156.1 ...
| Non-authoritative answer
| Recursive queries supported by this server
| Query for alisverissaati.com type=255 class=1
| alisverissaati.com TXT (Text Field)
| v=spf1 mx -all
| alisverissaati.com SOA (Zone of Authority)
| Primary NS: fenermarket.alisverissaati.com
| Responsible person: hostmaster@alisverissaati.com
| serial:119
| refresh:900s (15 minutes)
| retry:600s (10 minutes)
| expire:86400s (24 hours)
| minimum-ttl:3600s (60 minutes)
| alisverissaati.com A (Address) 192.168.1.100
| alisverissaati.com NS (Nameserver) fenermarket.alisverissaati.com
| alisverissaati.com NS (Nameserver) fenermarket.alisverissaati.com
| fenermarket.alisverissaati.com A (Address) 192.168.1.100

Your 'A' record points to an RFC 1918 IP address; I suspect that would be
the largest part of your problem. When MX lookups fail, a relay SMTP client
is supposed to fall back to the 'A' record for the destination domain; but
your 'A' record is not an Internet routable IP adderess, and it should be.
Start by fixing your domain 'A' record. Then try again.

--
Norman
~Oh Lord, why have you come
~To Konnyu, with the Lion and the Drum
NormanM

2007-02-20, 7:18 am

On Mon, 19 Feb 2007 17:51:19 -0500, PeterD wrote:

> Specifically make your RDNS name the same as the DNS name.


I would bet that he needs to fix his domain 'A' record, not his DNS/rDNS
names. Some mail servers don't like MX records pointing to 'CNAMES', and
some want to see a publicly routed IP address, not an RFC 1918 IP address,
in the 'A' record.

As I have already demonstrated, MSN Hotmail _DOES NOT_ reject on DNS/rDNS
mismatch. I have an example showing aosake.net/pacbell.net in the DNS/rDNS
positions, and MSN Hotmail accepted it just find.

--
Norman
~Oh Lord, why have you come
~To Konnyu, with the Lion and the Drum

2007-02-20, 7:18 am

Ok . When i fix my A record for mail.alisverissaati.com as 88.247.85.148 it
seems ok .

But there is one more problem . I also have some internal users and i have
an internal domain for alisverissaati.com

When i change it as 88.247.85.148 my internal users are not enable to reach
my web based email program. When i change it as 192.168.1.100 it seems ok .
How can i give the service for intrenal and external users at the same time
? Any idea ?


geek-y-guy

2007-02-20, 1:17 pm



--

<in da club> wrote in message news:eRK9zjMVHHA.1360@TK2MSFTNGP02.phx.gbl...
> Ok . When i fix my A record for mail.alisverissaati.com as 88.247.85.148
> it seems ok .
>
> But there is one more problem . I also have some internal users and i
> have an internal domain for alisverissaati.com
>
> When i change it as 88.247.85.148 my internal users are not enable to
> reach my web based email program. When i change it as 192.168.1.100 it
> seems ok . How can i give the service for intrenal and external users at
> the same time ? Any idea ?


You can configure split DNS so that users inside your subnet are returned
the 192.168.1.xxx records and users outside your network see the public IPs.
This is done in the DNS server itself.

Or, you can configure a second DNS server on your network that only handles
local queries, and point your inside clients to that server.

WHere are your DNS servers and what software are they running for DNS?


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