Net::SMTP and Unknown User

Hi,

Situation: I’ve got a program that automatically sends out emails to
large numbers of people in certain situations.

Problem: Sometimes people leave the company and their managers aren’t
always good about updating things. Since Net::SMTP#send_message seems
to be an “all or nothing” method (i.e. either an email is sent to
everyone or no email is sent to anyone), I’m not sure what to do about
this situation.

Things I’d like to avoid if possible:

LDAP: I’d rather not do an ldap lookup on every email address every
time an email is sent out. It’s slow, and seems like there ought to be
an easier solution.

Manual Parsing: I could parse the offending email out of the error
message, delete it from the array of email addresses and retry. But
that feels clunky and is probably error prone.

Suggestions?

Thanks,

Dan

On Thu, Aug 7, 2008 at 10:43 PM, Daniel B. [email protected]
wrote:

Problem: Sometimes people leave the company and their managers aren’t
always good about updating things. Since Net::SMTP#send_message seems
to be an “all or nothing” method (i.e. either an email is sent to
everyone or no email is sent to anyone), I’m not sure what to do about
this situation.

forgive me if i dont get you right, but why don’t you send/route the
mails to a real mail server and/or a mailing list server? A mail
server has builtin routing/retry/timeout mechnisms and
understands/implems the full smtp protocol.

kind regards -botp

On Aug 7, 9:08 am, botp [email protected] wrote:

understands/implems the full smtp protocol.
I’m afraid I don’t follow. Perhaps a bit of sample code will help:

require ‘net/smtp’

mhost = ‘mailgate.work.com
from = ‘[email protected]lid’

First email is valid, second one is not

to = [‘[email protected]’, ‘[email protected]’]

Raises a Net::SMTPFatalError

Net::SMTP.start(mhost, 25){ |smtp|
smtp.send_message(“hello”, from, to)
}

If this is the wrong approach, I’m all ears.

Thanks,

Dan

From: Daniel B. [mailto:[email protected]]
#DB: require ‘net/smtp’
#DB: mhost = ‘mailgate.work.com
#DB: from = ‘[email protected]
#DB: # First email is valid, second one is not
#DB: to = [‘[email protected]’, ‘[email protected]’]
#DB:
#DB: # Raises a Net::SMTPFatalError

NO, it should not (unless you reached the limit of the server’s max
recipient setting). what are the details of the error?

#DB: Net::SMTP.start(mhost, 25){ |smtp|
#DB: smtp.send_message(“hello”, from, to)
#DB: }

below is the actual code i used, adapted fr your code. i just modified
the params to work in my case and put some debugging so i know where in
the smtp session a certain error occurred just in case. i also show an
actual run. result is that i got one email for the test and another
bounced email for the dummy foo.bar address.

C:\family\ruby\mail>cat daniel.rb
require ‘rubygems’
require ‘net/smtp’

smtp_server = ‘bugomail.delmonte-phil.com
smtp_port = 25
from = ‘[email protected]

First email is valid, second one is not

to = [‘[email protected]’, ‘[email protected]’]

Raises a Net::SMTPFatalError

smtp = Net::SMTP.new(smtp_server, smtp_port)
smtp.set_debug_output $stderr # use for debugging; outputs mail
sessions
smtp.start { |smtp|
smtp.send_message(“this is a test”, from, to)
}

C:\family\ruby\mail>ruby daniel.rb
Connection opened: bugomail.delmonte-phil.com:25
-> “220 BUGOMAIL.delmonte-phil.com Microsoft ESMTP MAIL Service,
Version: 6.0.37
90.3959 ready at Sat, 9 Aug 2008 12:24:50 +0800 \r\n”
<- “EHLO localhost.localdomain\r\n”
-> “250-BUGOMAIL.delmonte-phil.com Hello [10.2.10.123]\r\n”
-> “250-TURN\r\n”
-> “250-SIZE\r\n”
-> “250-ETRN\r\n”
-> “250-PIPELINING\r\n”
-> “250-DSN\r\n”
-> “250-ENHANCEDSTATUSCODES\r\n”
-> “250-8bitmime\r\n”
-> “250-BINARYMIME\r\n”
-> “250-CHUNKING\r\n”
-> “250-VRFY\r\n”
-> “250-X-EXPS GSSAPI NTLM LOGIN\r\n”
-> “250-X-EXPS=LOGIN\r\n”
-> “250-AUTH GSSAPI NTLM LOGIN\r\n”
-> “250-AUTH=LOGIN\r\n”
-> “250-X-LINK2STATE\r\n”
-> “250-XEXCH50\r\n”
-> “250 OK\r\n”
<- “MAIL FROM:[email protected]\r\n”
-> “250 2.1.0 [email protected] OK\r\n”
<- “RCPT TO:[email protected]\r\n”
-> “250 2.1.5 [email protected] \r\n”
<- “RCPT TO:[email protected]\r\n”
-> “250 2.1.5 [email protected] \r\n”
<- “DATA\r\n”
-> “354 Start mail input; end with .\r\n”
writing message from String
wrote 19 bytes
-> “250 2.6.0 [email protected]
Queued ma
il for delivery\r\n”
<- “QUIT\r\n”
-> “221 2.0.0 BUGOMAIL.delmonte-phil.com Service closing transmission
channel\r
n”

C:\family\ruby\mail>

#DB: If this is the wrong approach, I’m all ears.

that approach is fine for small number of recipients. generally, mail
servers limit the number of recipients of a single mail.

So, for a big number (we do not care how many),

I. use a loop

Net::SMTP.start(mhost, 25){ |smtp|
to.each do |recipient|
smtp.send_message(“hello”, from, recipient)
end
end

II. or send to a mail_group address to the mail server configured w the
aliases, ie mail_group => [email protected], [email protected], …

III. or send to a mail_group address to a mail server capable of routing
it to a mailing list server (eg majordomo). this is the ideal setup for
big lists.

kind regards -botp

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