Postfix Relay via SendGrid Possible Authentication Issues?

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So I've been trying to setup postfix to relay via SendGrid with no luck. I got with SendGrid support and they were very helpful and we determined it's got to be on my side. I have a strong suspicion that the issue lies within my SASL config or possibly that SendGrid sees my server as trying to use user@hostname instead of my appropriate SendGrid username (user@domain.com). The error I see in the mail log that leads to think this is:

status=bounced (host smtp.sendgrid.net[174.36.32.204] said: 550 Cannot
receive from specified address <>: Unauthenticated senders not allowed (in reply
to MAIL FROM command))

I can provide more details, but really hope someone can lend me a hand! All this postfix installation will do for us is relay email for notifications and alerts via SendGrid.

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Jacob (Support Engineer) November 17, 2011 23:42

Hi Jeremy,

The "Unauthenticated senders not allowed" Generally means your system is not even trying the AUTH LOGIN step.

The proper steps are:
connect to smtp.sendgrid.net
EHLO
AUTH LOGIN
[username in base64]
[password in base64]
MAIL FROM:
RCPT TO:
DATA

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Hi Jeremy, The "Unauthenticated senders not allowed" Generally means your system is not even trying the AUTH LOGIN step. The proper steps are: connect to smtp.sendgrid.net EHLO AUTH LOGIN [username in base64] [password in base64] MAIL FROM: RCPT TO: DATA

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Jeremy Farr November 18, 2011 00:08

Ok, so what's the best place to start troubleshooting this? Simple telnet check?

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Ok, so what's the best place to start troubleshooting this? Simple telnet check?

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Isaac Saldana (Official Rep) November 18, 2011 07:22

Hi Jeremy,
You can get instructions for Postfix here http://docs.sendgrid.com/documentatio...

If you've already done that, then it would be nice to know what Linux distro you're using and if you have the SASL libraries installed.

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Hi Jeremy, You can get instructions for Postfix here http://docs.sendgrid.com/documentation/get-started/integrate/examples/postfix/ If you've already done that, then it would be nice to know what Linux distro you're using and if you have the SASL libraries installed.

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Jeremy Farr November 18, 2011 12:40

Thanks Isaac, I did see those instructions in my efforts. I'm using Ubuntu 10.04 LTS. I've got Cyrus installed as well. I checked this with postconf -a.

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Thanks Isaac, I did see those instructions in my efforts. I'm using Ubuntu 10.04 LTS. I've got Cyrus installed as well. I checked this with postconf -a.

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Jeremy Farr November 18, 2011 14:11

I also referenced this link in getting things configured:
http://marknelson.us/2011/07/06/sendm...

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I also referenced this link in getting things configured: http://marknelson.us/2011/07/06/sendmail-on-linux-the-easy-way/

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Isaac Saldana (Official Rep) November 21, 2011 00:24

Hi Jeremy,
I just got an instance from Rackspace with Ubuntu 10.04 LTS and did

apt-get install postfix libsas2-modules

Then I recorded the following video with instructions. The last command to install mailutils is only needed for an email client, feel free to ignore it.

Video at http://screencast.com/t/r15Iym5O92V

Please let me know if this helps.

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Hi Jeremy, I just got an instance from Rackspace with Ubuntu 10.04 LTS and did apt-get install postfix libsas2-modules Then I recorded the following video with instructions. The last command to install mailutils is only needed for an email client, feel free to ignore it. Video at http://screencast.com/t/r15Iym5O92V Please let me know if this helps.

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Jeremy Farr November 28, 2011 15:49

Thanks Isaac, I've been off for a few days. Viewing this now!

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Thanks Isaac, I've been off for a few days. Viewing this now!

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Jeremy Farr December 08, 2011 22:14

Isaac,
I've replicated this exactly as you did. Even had someone else on the IT staff do it for me. No luck. One thing I did notice is that in the logs the "from=" in the log seems to be empty:

Nov 23 14:37:15 testrelay postfix/qmgr[18825]: 80261100501: from=<>, size=2439, nrcpt=1 (queue active)
Nov 23 14:37:15 testrelay postfix/bounce[18829]: 16DA51004FF: sender non-delivery notification: 80261100501
Nov 23 14:37:15 testrelay postfix/qmgr[18825]: 16DA51004FF: removed
Nov 23 14:37:15 testrelay postfix/smtp[18827]: 80261100501: enabling PIX workarounds: disable_esmtp delay_dotcrlf for smtp.sendgrid.net[174.36.32.204]:25
Nov 23 14:37:15 testrelay postfix/smtp[18827]: 80261100501: to=, relay=smtp.sendgrid.net[174.36.32.204]:25, delay=0.35, delays=0/0/0.27/0.08, dsn=5.0.0, status=bounced (host smtp.sendgrid.net[174.36.32.204] said: 550 Cannot receive from specified address <>: Unauthenticated senders not allowed (in reply to MAIL FROM command))

In your example your log indicates "from=" and "from=" so somewhere I'm missing a setting somehow even though I followed your screencast to the T.

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Isaac, I've replicated this exactly as you did. Even had someone else on the IT staff do it for me. No luck. One thing I did notice is that in the logs the "from=" in the log seems to be empty: Nov 23 14:37:15 testrelay postfix/qmgr[18825]: 80261100501: from=<>, size=2439, nrcpt=1 (queue active) Nov 23 14:37:15 testrelay postfix/bounce[18829]: 16DA51004FF: sender non-delivery notification: 80261100501 Nov 23 14:37:15 testrelay postfix/qmgr[18825]: 16DA51004FF: removed Nov 23 14:37:15 testrelay postfix/smtp[18827]: 80261100501: enabling PIX workarounds: disable_esmtp delay_dotcrlf for smtp.sendgrid.net[174.36.32.204]:25 Nov 23 14:37:15 testrelay postfix/smtp[18827]: 80261100501: to=<root@testrelay.NOBLE.COM>, relay=smtp.sendgrid.net[174.36.32.204]:25, delay=0.35, delays=0/0/0.27/0.08, dsn=5.0.0, status=bounced (host smtp.sendgrid.net[174.36.32.204] said: 550 Cannot receive from specified address <>: Unauthenticated senders not allowed (in reply to MAIL FROM command)) In your example your log indicates "from=<root>" and "from=<root@testpostfix>" so somewhere I'm missing a setting somehow even though I followed your screencast to the T.

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Luke Ledet May 21, 2012 23:37

I am having this exact same problem after upgrading from Ubuntu 10.04 to Ubuntu 12.04. Has there been any resolution on this issue?

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I am having this exact same problem after upgrading from Ubuntu 10.04 to Ubuntu 12.04. Has there been any resolution on this issue?

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