Emails stuck in queue error 451 4.4.0 Primary target IP address ..

[Siv]

Hi,
I am running Windows SBS 2008 Server.

I am trying to set our outbound email to use a smarthost "smtp.surfdsl.net"
whenever I set up the SBS to use this smarthost mails start to pile up and if
I look at the oubound queues I can see an error alongside the outbound
comnnector which says:

451 4.4.0 Primary target IP address responded with: "421 4.2.1 Unable to
connect." Attempted failover to alternate host ..."

I cannot see why the "unable to connect" message is coming up? I have
checked the router's firewall settings and all outbound TCP and UDP is
allowed.

Inbound port 25 is port forwarded to the server's internal IP Address.

I have no Windows firewall rules that I can see that would be blocking this
(all outbound TCP and UDP is allowed and I can see no relevant exception
rules that would impede SMTP outbound).

Can anyone suggest why this is happening. For the time being I have had to
set the mail to direct delivery via DNS.

Any help appreciated.

Siv
--
Martley, Near Worcester, UK

[John Oliver, Jr. [MVP]]

Have you confirmed the ISP will let you do this? I assume they require some
type of SMTP Authentication, is this information correct?

--
John Oliver, Jr
MCSE, MCT, CCNA
Exchange MVP 2009
Microsoft Certified Partner

"Siv" <S...@discussions.microsoft.com> wrote in message
news:C1324D06-28A7-4A0E...@microsoft.com...

[Ed Crowley [MVP]]

On your SBS server open a command window and type the following (where
<smrthost> is the name or IP address of your smarthost exactly as you have
configured it in Exchange):

telnet <smarthost> 25

(You should see a banner from the smarthost.)

helo exchangeserver.company.com
mail from:y...@company.com
rcpt to:y...@yahoo.com
subject:Test Message
data
This is a test.
.
quit

Just before the quit, there's a period on a line by itself.

Post back with what happens. It'd be best to just copy the entire session
to the clipboard and paste it in your reply.
--
Ed Crowley MVP
"There are seldom good technological solutions to behavioral problems."
.

"Siv" <S...@discussions.microsoft.com> wrote in message
news:C1324D06-28A7-4A0E...@microsoft.com...

[Siv]

Ed,

Thnaks for your help with this.

This is the response:

Microsoft Windows [Version 6.0.6002]
Copyright (c) 2006 Microsoft Corporation. All rights reserved.

C:\Users\Siv>telnet smtp.surfdsl.net
Connecting To smtp.surfdsl.net...Could not open connection to the host, on
port
23: Connect failed

C:\Users\Siv>ping smtp.surfdsl.net

Pinging smtp.surfdsl.net [62.69.62.120] with 32 bytes of data:
Reply from 62.69.62.120: bytes=32 time=33ms TTL=59
Reply from 62.69.62.120: bytes=32 time=37ms TTL=59
Reply from 62.69.62.120: bytes=32 time=34ms TTL=59
Reply from 62.69.62.120: bytes=32 time=33ms TTL=59

Ping statistics for 62.69.62.120:
Packets: Sent = 4, Received = 4, Lost = 0 (0% loss),
Approximate round trip times in milli-seconds:
Minimum = 33ms, Maximum = 37ms, Average = 34ms

C:\Users\Siv>

Certainly doesn't seem to want to respond?? I decided to ping it just to see
if it would respond and it would as you can see.

Siv
--
Martley, Near Worcester, UK

"Ed Crowley [MVP]" wrote:

> On your SBS server open a command window and type the following (where
> <smrthost> is the name or IP address of your smarthost exactly as you have
> configured it in Exchange):
>
> telnet <smarthost> 25
>
> (You should see a banner from the smarthost.)
>
> helo exchangeserver.company.com
> mail from:y...@company.com
> rcpt to:y...@yahoo.com
> subject:Test Message
> data
> This is a test.

> ..

> quit
>
> Just before the quit, there's a period on a line by itself.
>
> Post back with what happens. It'd be best to just copy the entire session
> to the clipboard and paste it in your reply.
> --
> Ed Crowley MVP
> "There are seldom good technological solutions to behavioral problems."

> ..

[Siv]

John,

I checked with the ISP (Nine Telecom) and they claim they do not require
smtp authentication, however they are not the ultimate ISP, I have not been
able to contact Surfdsl directly. I am not sure if surfdsl are Nine Telecom
or whether Nine Telecom just piggy back on their systems. Our contract is
with Nine Telecom as provider of the ADSL connection.

Siv

--
Martley, Near Worcester, UK

[Ed Crowley [MVP]]

Please follow the instructions as I wrote them.

--
Ed Crowley MVP
"There are seldom good technological solutions to behavioral problems."
.

"Siv" <S...@discussions.microsoft.com> wrote in message
news:2EEB11B0-841C-4B45...@microsoft.com...

[Siv]

Ed,
I did and it gave a rejection so I didn't proceed any further as I assumed
the following stuff was dependent on the telnet login being accepted??

Siv
--
Martley, Near Worcester, UK

"Ed Crowley [MVP]" wrote:

> Please follow the instructions as I wrote them.
> --
> Ed Crowley MVP
> "There are seldom good technological solutions to behavioral problems."

[Ed Crowley [MVP]]

Please post the transcript of the commands and responses the way I
instructed you to enter them. Your previous post did not show that you
followed the instructions as I gave them to you.

--
Ed Crowley MVP
"There are seldom good technological solutions to behavioral problems."
.

"Siv" <S...@discussions.microsoft.com> wrote in message
news:29838838-3B84-48B3...@microsoft.com...

[Siv]

Ed,

Well if you look in my post I posted the command prompt and the reposnse I
get back, IE:

> >> > C:\Users\Siv>telnet smtp.surfdsl.net
> >> > Connecting To smtp.surfdsl.net...Could not open connection to the host,
> >> > on
> >> > port
> >> > 23: Connect failed

In other words at the command prompt I typed

telnet smtp.surfdsl.net

I am assuming the angle brackets are not part of the command as in your text
before that you say:

> >> >> <smrthost> is the name or IP address of your smarthost exactly as you
> >> >> have
> >> >> configured it in Exchange):

In exchange I have "smtp.surfdsl.net".

When I type that and press return I get the following response back:

Connecting To smtp.surfdsl.net...Could not open connection to the host, on
port
23: Connect failed

So after that error I gave up.

Can you be more specific about what I am doing wrong as I am now very
confused by your replies.

Siv

--
Martley, Near Worcester, UK

"Ed Crowley [MVP]" wrote:

> Please post the transcript of the commands and responses the way I
> instructed you to enter them. Your previous post did not show that you
> followed the instructions as I gave them to you.
> --
> Ed Crowley MVP
> "There are seldom good technological solutions to behavioral problems."

[Ed Crowley [MVP]]

Go back and read and follow what I told you to do, please.

--
Ed Crowley MVP
"There are seldom good technological solutions to behavioral problems."
.

"Siv" <S...@discussions.microsoft.com> wrote in message
news:25B4B914-73A3-4799...@microsoft.com...

[Siv]

Ed,
OK I get it I missed off the trailig port 25 in the Telnet command, couldn't
you have just said that and saved us both a heap of time. I am not familiar
with Telnet commands so it was not obvious to me what you were getting at?

OK so with the new knowlege we get this:

Microsoft Windows [Version 6.0.6002]
Copyright (c) 2006 Microsoft Corporation. All rights reserved.

C:\Users\Siv>telnet smtp.surfdsl.net 25

Connecting To smtp.surfdsl.net...Could not open connection to the host, on
port

25: Connect failed

C:\Users\Siv>

So I can no longer go any further I assume.

Siv
--
Martley, Near Worcester, UK

"Ed Crowley [MVP]" wrote:

> Go back and read and follow what I told you to do, please.
> --
> Ed Crowley MVP
> "There are seldom good technological solutions to behavioral problems."

[Ed Crowley [MVP]]

Exactly. Your Exchange server is unable to connect to host smtp.surfdsl.net
using SMTP--that's what the telnet to port 25 tests. Why that is I can't
tell you. You might look into firewall settings to start, or look into the
settings on smtp.surfdsl.net; perhaps it won't let you connect.

P.S. - You have a lot of nerve criticizing me for your repeated
unwillingness to admit to yourself that you might have made a mistake.

--
Ed Crowley MVP
"There are seldom good technological solutions to behavioral problems."
.

"Siv" <S...@discussions.microsoft.com> wrote in message
news:142FB5CB-9160-4AFD...@microsoft.com...

[Siv]

Ed,

The key point I was making that because of your slightly obtuse answers I
was not aware that I was making one.

If you had just said "Siv you forgot to include the port number in the
Telnet command" in your first response after asking me to carry out the
commands I would have been highly apologetic and admit (as I now do) that I
missed the 25 off the end of the line.

I said earlier I am not familiar with telnet, I have probably used it twice
in my entire career in IT which spans the best part of twenty years. It's
just a tool I have rarely used so I wouldn't instinctively know to put the
port number on the end of the command and for some reason missed it in your
post.

What irked me is the fact that instead of just helping me by telling what
you clearly knew after reading my first post after carrying out your
commands, you played this frankly childish game of re-iterating the order to
carry out your commands. OK I get it, you are a genius and I am thick for
not knowing what you were on about.

I appreciate that you give your help here for free and you probably get
irked that the people asking the questions can't follow simple commands, but
don't forget you know this stuff inside out, we may not and running us around
when we make a simple mistake helps no-one.

Siv
--
Martley, Near Worcester, UK

"Ed Crowley [MVP]" wrote:

> Exactly. Your Exchange server is unable to connect to host smtp.surfdsl.net
> using SMTP--that's what the telnet to port 25 tests. Why that is I can't
> tell you. You might look into firewall settings to start, or look into the
> settings on smtp.surfdsl.net; perhaps it won't let you connect.
>
> P.S. - You have a lot of nerve criticizing me for your repeated
> unwillingness to admit to yourself that you might have made a mistake.
> --
> Ed Crowley MVP
> "There are seldom good technological solutions to behavioral problems."

[Ed Crowley [MVP]]

I apologize for offending you. I've been doing this too long to get irked
too much.

--
Ed Crowley MVP
"There are seldom good technological solutions to behavioral problems."
.

"Siv" <S...@discussions.microsoft.com> wrote in message
news:4C6D9FB8-01F2-4037...@microsoft.com...

[Siv]

Ed,
I have been looking around on other internet sites after a lot of googling
and binging and have found another possibility that creeps into the equation,
apparently the SBS 2008 installation of Exchange 2007 implements ESMTP and in
particular sends an EHELO rather than a HELO (whatever that is??) I found a
commandlet command that you can run to turn this off which I have done (or at
least I think I have), the thinking being that teh smtp.surfdsl.net server is
rejecting us because we are using ESMTP comand rather than standard SMTP.

I am not sure about this because following your chain of commands the HELO
command didn't come in until after the connection (as I would expect), but I
don't know if Exchange server is sending the connection request in such a way
that the remote server can tell we are using ESMTP and is rejecting us out of
hand before we get to the EHELO??

I have raised a query with the ISP to see if they can raise the issue with
the ultimate ISP "SurfDSL" to try and find out why their server is rejecting
us, as after running your command (correctly) I then tried the same set of
commands to Demon's smtp server just to see what response it gave and sure
enough it replied back saying that our address was not allowed to connect to
it. To me this tells me that the commands are getting out from our network
on port 25 as Demon got it and told us we weren't allowed in. This means teh
ISP's original comment that we must be blocking port 25 outbound cannot be
right.

I will see if SurfDSL can tell me what is going on and what we can do to fix
it.

Siv
--
Martley, Near Worcester, UK

"Ed Crowley [MVP]" wrote:

> I apologize for offending you. I've been doing this too long to get irked
> too much.
> --
> Ed Crowley MVP
> "There are seldom good technological solutions to behavioral problems."

[Ed Crowley [MVP]]

The first command sent in an SMTP conversation is either EHLO or HELO. EHLO
is sent when ESMTP is supported. You can learn all about this by reading
the Internet RFCs. From the trasnscript of the TELNET session to the
server's port 25 you don't even get a banner so you can't even enter the
initial HELO or EHLO command.

--
Ed Crowley MVP
"There are seldom good technological solutions to behavioral problems."
.

"Siv" <S...@discussions.microsoft.com> wrote in message
news:E7FE306A-4D36-4073...@microsoft.com...

[Ruud]

Hi,

After removing McAfee Enterprise antivirus, everything was back to normal.
Outgoing mail is blocked by it.

Error message: 451 4.4.0 Primary target IP address responded with: ".”

Unable to
connect." Attempted failover to alternate host ...

Hopefully this information will help someone.

Regards,

Ruud

[adi...@artjconsultants.com]

I disabled Group shield and the problem is still there. Is there anything else to try?