Sendmail => Warning: could not send message for past 4 ho

What is this error message about? I'm banging my head for a long while, not finding a solution… I'll explain this in more details:

I have Sendmail configured inside one my linode box.

I relay from my home IP to send bulk emails.

I have been able to send like 1000emaisl already.

But then I got the errors:

Warning: could not send message for past 4 hours

SMTP -> ERROR: Failed to connect to server: Connection refused (111)

SMTP Error: Could not connect to SMTP host.

///mail.log:
> May 4 11:55:18 [mylinodename] sm-mta[2576]: p447oPuI018203: p44BjnLZ002576: sender notify: Warning: could not send message for past 4 hours

May 4 11:55:18 [mylinodename] sm-mta[2576]: STARTTLS=client, relay=aspmx.l.google.com., version=TLSv1/SSLv3, verify=FAIL, cipher=RC4-SHA, bits=128/128

May 4 11:55:18 [mylinodename] sm-mta[2576]: p447oPuI018203: to=<someone@adomain.info>, delay=04:04:50, xdelay=00:06:19, mailer=esmtp, pri=1114360, relay=adomain.info. [adomain's ip was here], dsn=4.0.0, stat=Deferred: Connection timed out with adomain.info.

As is, I can send email from within my box, because I test Sendmail in verbose mode and I also did telnet, it's working fine. But when I relay I get the error. My IP has been properly RELAYed in case you ask.

I also noted this error since last night. In morning, I was able to re-send another 500 emails, and then I got this email again.

So, I presume that in some 4hrs time, I might be able to re-send email again.

But how can I avoid (in case this deduction is correc)

5 Replies

It means it has been trying to send the e-mail for four hours, but has been unable to connect to adomain.info's mail server on port 25. delay=04:04:50 means that it has been trying for a total of 4 hours, 4 minutes, and 50 seconds, and xdelay=00:06:19 means it took 6 minutes, 19 seconds for this try.

Are all of these messages going to one place, or are they going to a bunch of different places? If the latter, does it affect just this destination or all destinations?

Is Google Apps involved at all? They have a 500/day limit for sending mail through a Google Apps account, which is suspiciously close to the number you're seeing.

Ultimately, you'll probably need to contact the postmaster of the receiving system to see if there are any limits in place. 500 e-mails to one place is a lot, and it is possible they're adding a temporary block to impede the flow.

@hoopycat:

It means it has been trying to send the e-mail for four hours, but has been unable to connect to adomain.info's mail server on port 25. delay=04:04:50 means that it has been trying for a total of 4 hours, 4 minutes, and 50 seconds, and xdelay=00:06:19 means it took 6 minutes, 19 seconds for this try.

Thanks for this specific info, I was not aware of this.

@hoopycat:

Are all of these messages going to one place, or are they going to a bunch of different places? If the latter, does it affect just this destination or all destinations?

No, it is going to several different emails.

By "does it affect just this destination or all destinations?", I assume you mean if one sending of one email locks in the possibility of sending the rest. No, it's just a loop in catch with will continue code execution in cases of Exceptions..

@hoopycat:

Is Google Apps involved at all? They hAave a 500/day limit for sending mail through a Google Apps account, which is suspiciously close to the number you're seeing.A

Google Apps is involved for the receiving part. For the sending, I use my linode box.

I have got 500+ bounces also in my gmail, does this affect why I cannot send email anymore via my home IP RELAYed?

I have another question:

1) Since I'm relaying emails from my home IP (which is from my local ISP) to my Linode box, do you think my ISP is limiting this relay?

hoopycat, thansk a lot for the response, really appreciate the help.

UPDATED:

I have tried doing the email sending executiong on my linode box itself. It works fine. But the RELAY from my home IP does not work anymore.

I suspect may be my ISP has filtered this RELAY or something?

A lot of ISPs block outgoing connections to port 25. (Some of them even admit to doing so!) Standard practice is to connect to your Linode on port 587 for mail submission using some form of authentication.

@Vance:

A lot of ISPs block outgoing connections to port 25. (Some of them even admit to doing so!) Standard practice is to connect to your Linode on port 587 for mail submission using some form of authentication.

Hi Vance,

ok I'll do that. Thanks for the response.

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