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550 5.7.1 Relaying denied.

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550 5.7.1 Relaying denied. - 10.Jul.2009 8:41:58 AM   
nightraider

 

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Joined: 9.Apr.2009
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Hi,

First of all sorry for asking a question that's not really about Exchange Server 2003, but I've seen so many useful things here that I thought it wouldn't hurt asking...
Our problem probably lies somewhere with our eSafe appliance, which we use to send and receive mail from. (so Exchange 2003 delivers to the appliance, which scans for spam/viruses and then mails, same way back)

Since a few days we're having trouble mailing to certain external addresses.
So most external addresses can be reached, and others are not delivered.

The mails that are not delivered are not returned to the sender, so there's no real NDR, which makes it hard to track the message.

For the mails that are not delivered we get the following type of messages back from eSafe (recipient mailaddress changed):

Details: Delivery MSG #911 - Email b5aaaa2b NOT sent after multiple retries, likely reason: 550 5.7.1 recipient@hotmail.com... Relaying denied.

and:

File Name-Mail Subject: Returned mail: unreachable recipients:recipient@hotmail.com
Details: Delivery MSG #911 - Email b5aab3ec NOT sent after multiple retries, likely reason: 554 5.1.0 Sender Denied.

We didn't change anything to our esafe or exchange config in the last days so I'm wondering why this would stop working all of a sudden.
Our exchange server is allowed to relay through the eSafe gateway and the eSafe gateway is allowed to relay on the exchange server.

I've already tried to use different SMTP Mail Relay servers on the appliace, but without any luck. Reverse DNS etc. is also all in order and working.

Can someone help me out? This has been bugging me for the whole week now and I can't seem to figure it out. Especially the part that we can mail 99% of the addresses without problems and just a few addresses/domains not.

Thanks in advance!

Regards,
Jeroen Trippe

< Message edited by nightraider -- 10.Jul.2009 8:43:41 AM >
Post #: 1
RE: 550 5.7.1 Relaying denied. - 10.Jul.2009 9:05:49 AM   
uemurad

 

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
Status: offline
Relaying means that the message is being delivered to a system that isn't responsible (authoritative) for the recipient address domain.

I had some trouble following your description of your mail flow, but let me give this a shot.

It sounds like your Exchange server passes all outbound messages to your eSafe appliance.  This is otherwise known as smarthosting.  When the outbound message is addressed to Hotmail, but first delivered to eSafe, that is relaying.  eSafe must be configured to allow that message to continue.  That is typically done with a whitelist either for the recipient address, or for the sending IP address (your Exchange server).  This would be done on the eSafe appliance if it has such a feature.

Since it sounds like some outbound messages work and others don't, based on recipient addresses, I would guess that the whitelist is based on recipient addresses instead of sending IP address.

You should be able to find evidence of the message delivery attempt on the Exchange server using Message Tracking, and viewing the SMTP log.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to nightraider)
Post #: 2
RE: 550 5.7.1 Relaying denied. - 12.Jul.2009 7:24:40 AM   
nightraider

 

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Joined: 9.Apr.2009
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I also posted this on the eSafe Forums, where I got this reply:

quote:

The error you see given not by eSafe but by the destination mail server.
This is not related to any changes on eSafe configuration.
As you can see destination server does not want to accept mail from eSafe due to:- unknown recipient- attempt to relay

possible the MAIL FROM was from the same domain as RCPT TO- sender denied
possible sender address in the black list of the mail server.
Sorry - but this is not eSafe problem in this case...


Full thread here.

I'll try bypassing eSafe for outgoing emails to see if this changes anything, though I doubt it will...

(in reply to uemurad)
Post #: 3
RE: 550 5.7.1 Relaying denied. - 12.Jul.2009 12:58:14 PM   
uemurad

 

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
Status: offline
I read the thread where you were told
quote:

when eSafe gives message 911 it always means - we can't send mail
That indicates that the error is because eSafe isn't able to forward the message.  Combining that information with how I defined relaying, it means that eSafe is attempting to send your message to a system that is refusing to accept delivery because the recipient address is something it thinks it is not responsible for.  As an example, if you addressed a message to hotmail.com and for some reason eSafe sent it to my corporate Email server, my system would reject the message as a relay attempt.

This is not to say that eSafe is necessarily at fault.  It could be the recipient domain has its DNS MX record configured inappropriately.  It could be that the recipient domain has changed its DNS MX record recently and eSafe has not yet refreshed the cached information.

It would be a good test to bypass eSafe to rule them out as the cause.  If you have a way to contact the administrators of the recipient domain, you can ask them if they are having the same problem with other senders, or if they have made any recent changes to their systems.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to nightraider)
Post #: 4
RE: 550 5.7.1 Relaying denied. - 13.Jul.2009 12:56:41 AM   
VijayaRelangovan

 

Posts: 172
Joined: 16.Mar.2009
From: Chennai, India
Status: offline
If your mail flow works like

Exchange -> Esafe -> internet

1. Then i would suggest you to drop an email through the telnet to the recipient domain name

For example : telnet mx4.hotmail.com 25
*mx4.hotmail.com -> mx record of hotmail.com

and check whether you can drop an email

2. If yes, then trying doing the same from Exchange server, this should fail atleast

3. If no, then Enable NCSA logging on DSMTPVS and send a test email again to hotmail.com

Check the NCSA log and search for that email, you will find a reason why it is not sending the email.

Even if that gives you same error message 5.1.0 Sender Denied, then it is worth enough to check for Blacklisting of ipaddress through known blacklist check websites.

(in reply to uemurad)
Post #: 5
RE: 550 5.7.1 Relaying denied. - 13.Jul.2009 2:04:48 AM   
nightraider

 

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Joined: 9.Apr.2009
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I've already checked the common blacklists and we're not on there (mail-dot-vanwijnen-dot-nl), I'll try telnetting to the remote side and dropping a mail.

(in reply to VijayaRelangovan)
Post #: 6
RE: 550 5.7.1 Relaying denied. - 13.Jul.2009 4:16:57 AM   
nightraider

 

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Joined: 9.Apr.2009
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I think I'm making progress now...

I just opened a telnet session from the eSafe appliance to the recipients mailserver (xs4all) and was able to send an email to a previously unreachable recipient using the smtp commands.

He replied to the email and I received it in my mailbox on our mailserver.

When I replied to that email it was not delivered again, so it seems like something IS actually wrong on OUR side :(

(in reply to nightraider)
Post #: 7
RE: 550 5.7.1 Relaying denied. - 13.Jul.2009 5:42:10 AM   
nightraider

 

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Joined: 9.Apr.2009
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I was able to extract this from the outgoing queue on the appliance, this is my reply on the mail I received after sending an email by telnetting:

(using quote because code result is realyl weird)
quote:


--------------------------------------------------------------------------------
Received: from mail<dot>vanwijnen<dot>nl ([172<dot>16<dot>1<dot>48]) by eSafe SMTP Relay 1247136277;
Mon, 13 Jul 2009 10:16:40 +0200
Content-class: urn:content-classes:message
MIME-Version: 1.0
Content-Type: text/plain; charset="us-ascii"
Content-Transfer-Encoding: quoted-printable
Disposition-Notification-To: "Trippe, J."
X-MimeOLE: Produced By Microsoft Exchange V6.5
Subject: RE: test email van wijnen
Date: Mon, 13 Jul 2009 10:16:56 +0200
Message-ID: <0F7CA709838D334A9E1C110539C564E60331F2BF@exbrn01<dot>wijnen<dot>local>
In-Reply-To: <164F646756D76D43822A409347EDEF1F0A72B0@SERVER03<dot>smit-beton<dot>lokaal>
X-MS-Has-Attach: X-MS-TNEF-Correlator:
Thread-topic: test email van wijnen
Thread-Index: AcoDkArO0ssl7S17TpqClorKZu0IkwAAJc4gAAB6d+A=
References: <164F646756D76D43822A409347EDEF1F0A72B0@SERVER03<dot>smit-beton<dot>lokaal>
From: "Trippe, J."
To: "Alfred Jonker"
X-ESAFE-STATUS:Mail clean
X-ESAFE-DETAILS: en deze krijg je weer niet denk ik?=20
-----Oorspronkelijk bericht-----
Van: Alfred Jonker [mailto:alfred<at>smit-beton<dot>nl]=20
Verzonden: maandag 13 juli 2009 10:05
Aan: Trippe, J.
Onderwerp: RE: test email van wijnen
Yep, gaat goed
-----Oorspronkelijk bericht-----
Van: j<dot>trippe<at>vanwijnen<dot>nl [mailto:j<dot>trippe<at>vanwijnen<dot>nl]
Verzonden: maandag 13 juli 2009 10:01
Aan: undisclosed-recipients:
Onderwerp: test email van wijnen test email, kan je deze beantwoorden?
*************************************************************************
Dit e-mail bericht is alleen bestemd voor de geadresseerde(n). Gebruik door anderen is niet toegestaan.
Indien u niet de geadresseerde(n) bent wordt u verzocht de verzender hiervan op de hoogte te stellen en het bericht te verwijderen.
Door de elektronische verzending kunnen aan de inhoud van dit bericht geen rechten worden ontleend.
*************************************************************************

dots changed to <dot>, @ changed to <at> to prevent spam.

I can't really figure out what's going wrong there...

(in reply to nightraider)
Post #: 8
RE: 550 5.7.1 Relaying denied. - 13.Jul.2009 10:10:13 AM   
VijayaRelangovan

 

Posts: 172
Joined: 16.Mar.2009
From: Chennai, India
Status: offline
So when you do a telnet to the external domain, you were able to drop an email. right?
if yes, try to drop an email through telnet from the exchange server to esafe to drop an email to the external domain (This is just like trying to relay through esafe).
(OR)
You can also try to reroute the mail directly to the external domain instead of routing it through the esafe.
This way you can figure out whehter exchange or the esafe is causing you the problem

with regards,
Vijay

(in reply to nightraider)
Post #: 9
RE: 550 5.7.1 Relaying denied. - 13.Jul.2009 12:28:46 PM   
nightraider

 

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Joined: 9.Apr.2009
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I've tried to drop a mail directly from the exchange server now using telnet, though I'm not sure if the recipient will actually receive it since my internet ip is different from the internet ip that the eSafe appliance has.

At least it said message accepted.
Will know tomorrow (CET timezone here) if he actually got the mail.

(in reply to VijayaRelangovan)
Post #: 10
RE: 550 5.7.1 Relaying denied. - 14.Jul.2009 2:26:12 AM   
nightraider

 

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Joined: 9.Apr.2009
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I just got a reply from the recipient on my mail from the exchange server, so this works as well..

(in reply to nightraider)
Post #: 11
RE: 550 5.7.1 Relaying denied. - 14.Jul.2009 10:47:04 AM   
VijayaRelangovan

 

Posts: 172
Joined: 16.Mar.2009
From: Chennai, India
Status: offline
If mail directly from the exchange server to the external domain works, then you cannot do much on the exchange.

you have to work on the esafe to fix this issue

(in reply to nightraider)
Post #: 12
RE: 550 5.7.1 Relaying denied. - 14.Jul.2009 11:58:44 AM   
nightraider

 

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Joined: 9.Apr.2009
Status: offline
well it was a telnet mail, gonna try to bypass the esafe appliance now to see if the mail is delivered.

(in reply to VijayaRelangovan)
Post #: 13
RE: 550 5.7.1 Relaying denied. - 14.Jul.2009 3:41:46 PM   
nightraider

 

Posts: 20
Joined: 9.Apr.2009
Status: offline
well when I tried sending directly from Exchange I couldnt get any mail to the outside world... probably because our Exchange server is not in the DMZ and therefor has a different internet IP than our mx record (so reverse dns check wil always fail).

(in reply to nightraider)
Post #: 14
RE: 550 5.7.1 Relaying denied. - 15.Jul.2009 2:51:40 AM   
VijayaRelangovan

 

Posts: 172
Joined: 16.Mar.2009
From: Chennai, India
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ok. For testing purpose

1. Create a SMTP connector
2. With address spaces as *@hotmail.com
3. And the smart host has 65.55.92.136
4. Send a test email to hotmail.com

Now the email that is sent to hotmail account directly goes to the ipadderss(hotmail)

If this works, again, its not a problem with the exchange.

(in reply to nightraider)
Post #: 15
RE: 550 5.7.1 Relaying denied. - 15.Jul.2009 8:23:52 AM   
uemurad

 

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
Status: offline
Does the eSafe appliance have any sort of logging for its SMTP communications?  If so, look for the the connection information for one of the failed messages to see where it is sending the message, and what SMTP response codes each of the commands receives.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to VijayaRelangovan)
Post #: 16
RE: 550 5.7.1 Relaying denied. - 15.Jul.2009 8:36:24 AM   
nightraider

 

Posts: 20
Joined: 9.Apr.2009
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Well I got fed up with trying and not getting anywhere ;-)
The problem is now being investigated by eSafe support, will keep you informed!

(in reply to uemurad)
Post #: 17

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