Exchange 2003 SMTP Error

A

Asha'man X

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Hi everyone.

After lurking forever, I've finally decided to post, and I'm in search of help.

My question is as follows:

We have an Exchange 2003 SP2 server that handles all the mail for our school. Works great, no problems except one. Twice now when staff members have tried to send messages to people with Yahoo addresses, they get a message from the server with the following contents:

"Your message did not reach some or all of the intended recipients.

Subject: xxxxxxxxxx
Sent: 2007/11/05 13:20

The following recipient(s) could not be reached:

[email protected] on 2007/11/05 13:23
You do not have permission to send to this recipient. For assistance, contact your system administrator.
<server01.xxx.xxx.xxx#5.7.1 smtp;550 5.7.1 550 Multi Recip block on Yahoo mail>

[email protected] on 2007/11/05 13:23
You do not have permission to send to this recipient. For assistance, contact your system administrator.
<server01.xxx.xxx.xxx#5.7.1 smtp;550 5.7.1 550 Multi Recip block on Yahoo mail>

[email protected] on 2007/11/05 13:23
You do not have permission to send to this recipient. For assistance, contact your system administrator.
<server01.xxx.xxx.xxx#5.7.1 smtp;550 5.7.1 550 Multi Recip block on Yahoo mail>"

N.B Additonal output snipped for brevity

I have searched the internet silly but can't seem to find any help with this problem. Closest I get is with the 5.7.1 and 550 Error codes, but nothing on the Multi Recip block thing.

Does anyone know what could be causing this error? One of the staff was using Outlook XP, and the other Outlook Web Access. From what I have managed to find out, the local Exchange server is rejecting the message. How and why I don't know, I can't find any settings in Exchange System Manager that enables or disables any block to Yahoo.

If anyone can help, I'd really appreaciate it.

TIA

Asha'man X
 
Ive had a similar problem when Outlooks default mail composer is Microsoft word. Change it to send the message as plain text or HTML and see if that makes any difference.
 
Checkout the following post from MSFT to see if you have a
PTR record for your smtp server,as some remote email servers
check to see if your IP address maps to the domain name
Prevent spammers who use DSL for spamming users.
If you that is so then you might have to find a relay server
to relay your email. Try smtp.saix.net if it is not blacklisted
if you connect to the DSL network or who ever your ISP is.

http://support.microsoft.com/kb/300171
http://searchexchange.techtarget.co...ebaseAnswer/0,289625,sid43_gci1155538,00.html

http://spamcop.net/w3m?action=checkblock&ip=196.25.240.94
IP address for smtp.saix.net
 
Last edited:
Or simply set your SMTP server to use DNS for mail delivery and make sure you have an SPF record as well.
Also try disabling the built in SPAM filter to check if you can send straight through.

Just checking, so this is your server address? server01.xxx.xxx.xxx
 
Last edited:
Most likely its some noob receptionist sending a message to multiple yahoo receipts at once.

Steps to take

1. Send a message with only 1 receiptent to that yahoo account
2. Your exchange is most using a smart host ( ie smtp.saix.net etc , and that mail server is bitching that your exchange is sending to too many recipents)
3. If the problem still continues , change from Smart host relay to MX Direct.
 
Thanks guys for your help, really appreciated.

I didn't include some info in my first post as it was getting so long already.
We are on DSL 512 kb/s with our ISP, Froogfoot. Outgoing mail in Exchange is sent through a connector to smtp.saix.net.

At one stage we tried using DNS to deliver mail but ended up with many bounced messages and other bizzare problems. So went back to mail relay and it has worked flawlessly since. We don't get incoming mail delivered directly to our server, it sits in our ISP "catch all" POP3 account and we have a program that fetches the mail, then feeds it to Exchange's SMTP server for delivery into the network.

After doing some thought based on what Juggy said
Also try disabling the built in SPAM filter to check if you can send straight through
Click to expand...
I may have an idea.

If I remember correctly this problem never occurred until I used some of the built in SPAM detection tools in SP2 of Exchange 2003. When the server was still plain Exchange 2003 (no service pack) and Exchange 2000 before that, I never had this issue.

If my memory is correct, when sending mail to external users, the internal Exchange format is converted into standard SMTP format, and it might be at that point when the server rejects messages to the Yahoo contacts, based on the SPAM filters implemented into SP2 or something similar.

I will try and reduce the spam filter level and see if that helps.

If anyone has any further ideas or can see a flaw in my logic, I would appreciate it. Thanks again for all the help guys.

Asha'man X :)
 
Did you ever fix this problem?

I have the same one and it's not even a exchange server. Also relaying via SAIX, and with a totally abused DSL line wouldn't be able to send much messages direct.

Wed 2008-04-16 12:04:20: Session 2257; child 1
Wed 2008-04-16 12:04:16: Parsing message <c:\mdaemon\queues\remote\pd50000001254.msg>
Wed 2008-04-16 12:04:16: * From: [email protected]
Wed 2008-04-16 12:04:16: * To: [email protected]
Wed 2008-04-16 12:04:16: * Subject: Workaway
Wed 2008-04-16 12:04:16: * Message-ID: <009f01c89fa9$8ef1cd80$0419a8c0@Charlotte>
Wed 2008-04-16 12:04:16: Attempting SMTP connection to [smtp.saix.net]
Wed 2008-04-16 12:04:16: Resolving MX records for [smtp.saix.net] (DNS Server: 196.25.1.11)...
Wed 2008-04-16 12:04:16: * Name server has no records of the requested type for that domain
Wed 2008-04-16 12:04:16: Attempting to send message to smart host
Wed 2008-04-16 12:04:16: Attempting SMTP connection to [smtp.saix.net:25]
Wed 2008-04-16 12:04:16: Resolving A record for [smtp.saix.net] (DNS Server: 196.25.1.11)...
Wed 2008-04-16 12:04:16: * D=smtp.saix.net TTL=(2) A=[196.25.240.94]
Wed 2008-04-16 12:04:16: Attempting SMTP connection to [196.25.240.94:25]
Wed 2008-04-16 12:04:16: Waiting for socket connection...
Wed 2008-04-16 12:04:16: * Connection established (192.168.25.1:4945 -> 196.25.240.94:25)
Wed 2008-04-16 12:04:16: Waiting for protocol to start...
Wed 2008-04-16 12:04:16: <-- 220 ctb-mesg-2-2.saix.net ESMTP Postfix
Wed 2008-04-16 12:04:16: --> EHLO domain.co.za
Wed 2008-04-16 12:04:16: <-- 250-ctb-mesg-2-2.saix.net
Wed 2008-04-16 12:04:16: <-- 250-PIPELINING
Wed 2008-04-16 12:04:16: <-- 250-SIZE 102400000
Wed 2008-04-16 12:04:16: <-- 250-ETRN
Wed 2008-04-16 12:04:16: <-- 250-ENHANCEDSTATUSCODES
Wed 2008-04-16 12:04:16: <-- 250-8BITMIME
Wed 2008-04-16 12:04:16: <-- 250 DSN
Wed 2008-04-16 12:04:16: --> MAIL From:<[email protected]> SIZE=32293
Wed 2008-04-16 12:04:16: <-- 250 2.1.0 Ok
Wed 2008-04-16 12:04:16: --> RCPT To:<[email protected]>
Wed 2008-04-16 12:04:16: <-- 250 2.1.5 Ok
Wed 2008-04-16 12:04:16: --> DATA
Wed 2008-04-16 12:04:16: <-- 354 End data with <CR><LF>.<CR><LF>
Wed 2008-04-16 12:04:16: Sending <c:\mdaemon\queues\remote\pd50000001254.msg> to [196.25.240.94]
Wed 2008-04-16 12:04:18: Transfer Complete
Wed 2008-04-16 12:04:19: <-- 550 5.7.1 550 Multi Recip block on Yahoo mail
Wed 2008-04-16 12:04:19: --> QUIT
Wed 2008-04-16 12:04:20: <-- 221 2.0.0 Bye
Wed 2008-04-16 12:04:20: SMTP session terminated (Bytes in/out: 289/32439)
Wed 2008-04-16 12:04:20: ----------
 
I have a rule of always adding SPF records for each server that will be sending email to make sure I'm as compliant as possible for all email system. Also make sure you have a PTR record as well for reverse lookups.

Also, Hotmail, Yahoo, Gmail etc will block you if you send large ammounts at a time to their system as well as many in the BCC or TO fields.
 
@ Ivork

Unfortunately, I never really got the bottom of it. Luckily we haven't had anybody try to send multiple messages to Yahoo based addresses recently.

I let people know that it was a Yahoo restriction and that they should just send mails one by one to Yahoo. Painful, but out of my hands really.

@ JUGGY

How do you set up a SPF record for Exchange? I've looked around in both Exchange and DNS, but can't find any mention of it.
 
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