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501 5.5.4 Invalid Address EXchange 2003

Hi

If my smtp on my Exchange server 2003 receive a mail with more than one in the from field (xx@xxx.com; yy@yyy.com) it fails with the following message:

220 EXCH01.cargodom.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959 ready at  Fri, 3 Sep 2010 08:56:48 +0200
helo
250 EXCH01.cargodom.local Hello [10.10.20.109]
mail from: xx@xxx.com; ee@eee.com
501 5.5.4 Invalid Address

The same happens sometimes when I receive mails with multiple recipient.

The recipient in the from or to field are separated with semicolon.
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DANCARGO
Asked:
DANCARGO
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1 Solution
 
Alan HardistyCommented:
If the above message has not been adjusted at all then it is because the IP Address of 10.10.20.109 is a non-valid Internet IP Address - it is a reserved IP address and is not internet routeable.
Also, the FQDN EXCH01.cargodom.local is also not a routeable domain name as it is reserved for local networks, so change the FQDN on your SMTP Virtual Server Properties, Delivery Tab, Advanced button to something like mail.cargodom.com (or whatever resolves to your mail server) and then try again.
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DANCARGOAuthor Commented:
My Exchange server is located on my local LAN, I have another server located in DMZ for connection to the internet.

Server1 which I am sending mails from is also located on my local LAN, the software on server1  is sending mail to the exchange server with local recipient in the from field.

So I don´t suspect that it should be a routing problem.
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Alan HardistyCommented:
I didn't say it was a routing problem - I said that the IP Address and Fully Qualified Domain Name you posted above are not ones that will resolve to the rest of the world because they are internal (IP Address and domain name).
 
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DANCARGOAuthor Commented:
That´s correct, I use my spam server as the external part which have a WAN ip and Fully Qualified Domain Name, and that part work perfect.

But my problem is at the internal part, my SMTP on my Exchange accept mails if only one recipient in the from filed, but if is use more than one recipient it fails.

Telnet example:

220 EXCH01.cargodom.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959 ready at  Fri, 3 Sep 2010 08:56:48 +0200
helo
250 EXCH01.cargodom.local Hello [10.10.20.109]
mail from: xx@xxx.com; ee@xxx.com
501 5.5.4 Invalid Address
0
 
Alan HardistyCommented:
>>But my problem is at the internal part, my SMTP on my Exchange accept mails if only one recipient in the from filed, but if is use more than one recipient it fails.<<
Mails can only come From one person - not multiple people.  Do you mean the To: Field?
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DANCARGOAuthor Commented:
If I only use one recipient in from: then i get the same mesage if i use more than one in the to: field.

Example:

220 EXCH01.cargodom.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959 r
eady at  Fri, 3 Sep 2010 14:57:39 +0200
helo
250 EXCH01.cargodom.local Hello [10.10.20.109]
mail from: aa@xxx.com
250 2.1.0 aa@xxx.com....Sender OK
rcpt to: bb@xxx.com; ee@xxx.com
501 5.5.4 Invalid Address
0
 
Alan HardistyCommented:
Can you please explain exactly what it is that you are trying to do and why it is a problem.
Are you trying to manually send out mail, or use a 3rd party application to send out mail, or are you using Exchange and Outlook and having problems?
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DANCARGOAuthor Commented:
I have a 3rd party application which send out invoices to our customers.

The 3rd party application send email to my exchange server whic forward the mails to the spam(smtp gateway) which send them to the customers.

the 3rd party application is setup to send the mail to the costumer, and some internal persons in our company. If we only use 1 email address in the recipent field then it works, if we use 2 emails or more in the recipient field then it fails.

Then I made a telnet to my exchange on port 25 to test:

Example:
220 EXCH01.cargodom.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959 r
eady at  Fri, 3 Sep 2010 14:57:39 +0200
helo
250 EXCH01.cargodom.local Hello [10.10.20.109]
mail from: aa@xxx.com
250 2.1.0 aa@xxx.com....Sender OK
rcpt to: bb@xxx.com; ee@xxx.com
501 5.5.4 Invalid Address

Why do i get 501 5.5.4 Invalid Address every time when the i more than one recipient?
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Alan HardistyCommented:
Ok - thanks.  Understood now.
The RCPT TO: commands have to be sent separately, not on the same line.
The commands should be:
helo
mail from: aa@xxx.com
rcpt to: bb@xxx.com
rcpt to: ee@xxx.com
etc
 
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DANCARGOAuthor Commented:
You should be able to send it in one line with semicolon as seprating
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Alan HardistyCommented:
Not from the tests I have been doing - it does work with separate lines though.
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DANCARGOAuthor Commented:
I didn´t get the correct answer, just how it worked in his system
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Alan HardistyCommented:
If that is the case - What is the 'Correct' answer?
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