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Merlin-Eng
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Mail not being received

SBS2008 + Exchange2007  External mail is being received perfectly normally. The only issue I have is with mail from  an internal smtp program called Postie.exe. It stopped working a few months ago.

The Postie program is being used by our manufacturing database application. It sends emails to internal users to notify them about various issues within the database.

When look at the Exchange smtp receive log, I see something like this:

+,,
*,SMTPSubmit SMTPAcceptAnyRecipient SMTPAcceptAnySender SMTPAcceptAuthoritativeDomainSender AcceptRoutingHeaders,Set Session Permissions
>,"220 ourserver.ourdomain.co.uk Microsoft ESMTP MAIL Service ready at Fri, 21 Apr 2017 11:58:01 +0100",
<,EHLO aclient.ourdomain.local,
>,250-ourserver.ourdomain.co.uk Hello [192.168.16.51],
>,250-SIZE 20971520,
>,250-PIPELINING,
>,250-DSN,
>,250-ENHANCEDSTATUSCODES,
>,250-STARTTLS,
>,250-AUTH,
>,250-8BITMIME,
>,250-BINARYMIME,
>,250 CHUNKING,
<,MAIL FROM:<aclient@ourdomain.co.uk>,
,*,08D488736BF69D73;2017-04-21T10:58:02.171Z;1,receiving message
>,250 2.1.0 Sender OK,
<,"RCPT TO:<anothercient@ourdomain.co.uk> NOTIFY=DELAY,FAILURE ORCPT=rfc822;anotherclient@ourdomain.co.uk",
>,250 2.1.5 Recipient OK,
<,DATA,
>,354 Start mail input; end with <CRLF>.<CRLF>,
>,250 2.6.0 <c120e33b-22a8-45c2-a2eb-46986b99da80@server.ourdomain.local> Queued mail for delivery,
<,QUIT,
>,221 2.0.0 Service closing transmission channel,
-,,Local

To me, that looks ok but email from the postie program never reaches it's destination these days. I don't know what changed. Can anyone help?
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Patrick Bogers

8/22/2022 - Mon
Patrick Bogers

Hi

Check your recieve and or relay connector, chances are the IP address from which the emails originate aren't white listed.

Cheers
Merlin-Eng

ASKER
I have Receive Connector called "Internal Relay". It doesn't have a White List that I can configure. But in the log I posted above, it states the mail was queued for delivery. Does this statement not imply that the mail has passed all tests and has been accepted?
Merlin-Eng

ASKER
In Server Configuration -> Hub Transport the server has a white list. All the internal address space has always been white listed.
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James Murphy
Patrick Bogers

NOTIFY=DELAY,FAILURE
Shows there is a issue where it is not yet decided if the outcome will be a delay or a failure.
Since you don't get the mails, even with delay, we can conclude it ended in failure, question remaining is why.

What does Exchange Queue Viewer tells you?
Merlin-Eng

ASKER
Are you sure about this? When I googled that statement, I found a page saying that this means that  the sender is stating that he is prepared to be notified about delays or failures.
Patrick Bogers

The last option is DELAY: you will be notified if there is an unusual delay in delivery, but the actual delivery's outcome (success or failure) is not yet decided. NEVER must be the only argument if it specified, the other three may appear in a list, delimited by a comma. SUCCESS and FAILURE make up for a pretty strong team together(!), telling you in (almost) any case what happened to your mail.

Source for this quote: https://www.lifewire.com/what-is-dsn-delivery-status-notification-for-smtp-email-3860942
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Merlin-Eng

ASKER
OK. So I think we are in agreement on the meaning of the NOTIFY statement. At the point that it appears in the smtp log, the outcome has not been determined. But the smtp log goes on to state that the mail has bee queued for delivery. So I still need to know how to troubleshoot this further,

Thanks for your input so far by the way.
Patrick Bogers

Np

What does Exchange Queue Viewer tells you?
Merlin-Eng

ASKER
I feel embarrassed now. I never heard of Exchange Queue Viewer. Where do I find this?
I started with Experts Exchange in 2004 and it's been a mainstay of my professional computing life since. It helped me launch a career as a programmer / Oracle data analyst
William Peck
Patrick Bogers

In 2007 it should be in EMC under toolbox.
Merlin-Eng

ASKER
Ok I found that thanks. I cannot find anything loitering in there. It all seems empty.
Patrick Bogers

Ok, then I would initiate a telnet session from the server hosting this app and send a manual mail.
You can then track this mail via message tracking and see where it goes.

This is a good how to on doing it http://www.yuki-onna.co.uk/email/smtp.html
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Merlin-Eng

ASKER
Would you believe that my windows 10 pc doesn't have telnet? i'll try and get it some how.......
Patrick Bogers

Is your windows 10 pic the machine where this app resides on?
Oh yes I can imagine ms left it disabled, not anybody needs it.

Run a command prompt as admin and run.     dism /online /Enable-Feature /FeatureName:TelnetClient
In a few seconds telnet is enabled.
Merlin-Eng

ASKER
ok that worked thanks. I'll give telnet a try now.....
Your help has saved me hundreds of hours of internet surfing.
fblack61
Merlin-Eng

ASKER
OK, I stepped through that article and sent a message to myself. In the command prompt window it stated that the message had been queued for delivery. The smtp recieve log stated the same also, but I never received it.

Before i ran the telnet program I went into OrganisationConfiguration -> Hub Transport -> Anti Spam and disabled everything.

I've just noticed something  in the smtp receive log..... At the end of the conversation there is the line:

250 2.6.0 <3c9afc57-33ba-4dd6-b656-0c2576217f48@server.ourdomain.local> Queued mail for delivery

When I look at other entries where the mail was received successfully, the 250 2.6.0 line contains the senders domain rather than our own. Is this relevant?
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Patrick Bogers

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Merlin-Eng

ASKER
OK I found the problem, and it is of my own creation.....  You gave me the hint by suggesting I look at the server anti-virus.

Several months ago we were getting a lot of junk emails which spoofed someone from within our organisation as the sender address. So i created a transport rule to silently drop messages which came from outside of the organisation with one of our users  as the sender. It turns out that emails received on the internal smtp connector are also being regarded as originating from outside the organisation. So I can fix this now.

Thank you very much for your help. It is much appreciated.

Ian
Patrick Bogers

Nice!! Thank you for the good explanation what went wrong and who is to blame :)
This will help future readers.

Cheers
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