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#1842 ✓committed
Matt Jones

ActionMailer doesn't correctly use return-path header

Reported by Matt Jones | February 2nd, 2009 @ 06:00 AM

When sending emails with a return-path set, using the :smtp delivery method, ActionMailer sends an invalid MAIL FROM header. The problem arises from the use of mail['return-path'] in perform_delivery_smtp; TMail returns a TMail::ReturnPathHeader, which picks up an extra set of gt/lt signs when converted to a string. Net::SMTP already encloses the address, and badness ensues.

Short code example (try it in a script/console):

m =
m['return-path'] = ''

# => "<>"

# => ""

Changing the relevant line (line 675, base.rb) to use mail['return-path'].spec would seem to solve this problem cleanly.

This isn't caught by the tests, as all the tests use MockSMTP, which doesn't exhibit this behavior.

Given that this is a five-character change, does it need a patch?

Comments and changes to this ticket

  • Chris Hapgood

    Chris Hapgood February 3rd, 2009 @ 05:06 PM

    Hmmmm. I just ran a test and can't see the double quotes. Yet I'm pretty sure I have seen them in the past.

    My versions: Rails.version => 2.2.2 Net::SMTP::Revision => "11708"

  • Chris Hapgood

    Chris Hapgood February 3rd, 2009 @ 06:30 PM

    Whoops. I had the delivery method set to sendmail on my staging machine. As soon as a I set it to smtp, I do indeed see the double angle brackets around the return path address.

    From my sendmail log:

    Feb  3 13:24:56 osprey sendmail[30343]: n13IOuNd030343: from=<<>>, size=2379, class=0, nrcpts=1, msgid=<>, proto=ESMTP, daemon=MTA, relay=localhost.localdomain []

    Matt, I would suggest you upload a patch at a minimum. Testing it will indeed be a b!&%#.

    +1 to fix this!

  • Matt Jones

    Matt Jones February 3rd, 2009 @ 08:04 PM

    • Tag changed from 2.3, actionmailer, bug to 2.3, actionmailer, bug, patch

    Worked up a patch - given that Net::SMTP's behavior is known, I added an assertion to the existing Return-Path test to check the address is correctly formatted.

    I recommend MailTrap to listen in on the SMTP conversation. Before the patch, the output (in mailtrap.output, not mailtrap.log) from a mailer that set the Return-Path:

    Helo: EHLO
    Seen an EHLO
    From: MAIL FROM:<<>>
    To: RCPT TO:<>
    + Return-Path: <>
    + Date: Tue, 3 Feb 2009 14:34:23 -0500
    + From:
    + To:
    + Message-Id: <49889c3f1cd8f_db11a37e3db@matt-jones-computer.local.tmail>
    + Subject: test mail
    + Mime-Version: 1.0
    + Content-Type: text/plain; charset=utf-8
    + Blah blah blah!!!
    + Blah blah blah!!!
    + Blah blah blah!!!
    And we're done with that bozo!

    Note the extra brackets on the MAIL FROM line. The patch fixes it.

  • Repository

    Repository February 5th, 2009 @ 07:54 PM

    • State changed from “new” to “committed”

    (from [250dfb18afb58dda3caf4b9f170ddb9c5cf85faf]) Fixed that ActionMailer should send correctly formatted Return-Path in MAIL FROM for SMTP [#1842 state:committed]

    Signed-off-by: David Heinemeier Hansson

  • Yar Dmitriev

    Yar Dmitriev September 4th, 2010 @ 02:48 AM

    Rails 2.3.8, production mode

    config.action_mailer.delivery_method = :sendmail

    An attempt to specify:

    headers "return-path" => "user@domain.tld"

    results in the envelope-from value being <user@domain.tld>, which cases the message to be bounced back.

    The patch is attached.

  • Yar Dmitriev

    Yar Dmitriev September 4th, 2010 @ 02:50 AM

    Of course, I meant double angular brackets - the parser shows them as singular here.

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