action mailer can't deliver mail via smtp on ruby 1.9.1 or 1.8.7

I can confirm this bug. In postfix it gives this:

warning: Illegal address syntax from unknown[xx.xx.xx.xx] in MAIL command: ["user@example.com"]

The exception in rails itself:

Net::SMTPSyntaxError 501 5.1.7 Bad sender address syntax

Let's hope that this comment makes it easier to google this problem.

Anyway thanks for the fix!

+1 from me. i get the same error with postfix.

+1 from me too, getting the exact same error right now with postfix

This commit broke SMTP sends in my Rails project (on Ruby 1.8).

When the TMail object is instantiated with a From header that includes a recipient name and email address (e.g. "John Doe john@doe.com"), mail.from returns just the email address (e.g. "john@doe.com"), which is the correct syntax for SMTP's MAIL FROM command. However, mail['from'] returns the verbatim From string (e.g. "John Doe john@doe.com") which is invalid syntax and causes the SMTP server to barf.

Breaking support for named senders in exchange for Ruby 1.9 compatibility isn't an acceptable tradeoff. If you don't want an array, the sender.first solution is the right one.

Here's a patch that fixes the pre-1.9 issue for me. I've included the tests provided by Josh Nichols at #2945 ActionMailer generates invalid SMTP commands when from contains name.

Previous link got corrupted. Here's the other thread:

#2945 ActionMailer generates invalid SMTP commands when from contains name

+1 for Joey A's patch!

just applied it to our production app, it saved our night
this bug is a real showstopper...

Joey,

Could you attach it as a proper git format-patch patch, that way
you'll get the right credit.

Happy to apply to 2-3-stable and master, will be fixed in 2.3.4

attached is Joeys patch as git-format-patch.

+1, as I was running into it on #2945 ActionMailer generates invalid SMTP commands when from contains name :) I verified the patch addresses the problem on 1.8 and 1.9.

Given the mailer:

class Blah < ActionMailer::Base

  def blah
    from "Tester McTesty <test@test.com>"
    recipients "Josh Nichols <josh@technicalpickles.com>"
    subject "blah"
  end
  
end

Output before the patch is incorrect for 1.8 and 1.9, according to mailtrap:

* Message begins
From: <Tester McTesty <test@test.com>>
To: <josh@technicalpickles.com>
Body:
Date: Sat, 8 Aug 2009 11:43:40 -0400
From: Tester McTesty <test@test.com>
To: Josh Nichols <josh@technicalpickles.com>
Message-Id: <4a7d9d2ce0ff_540558b421df@technicalpickles.local.tmail>
Subject: blah
Mime-Version: 1.0
Content-Type: text/plain; charset=utf-8

* Message ends

After applying the patch, it is corrected:

* Message begins
From: <test@test.com>
To: <josh@technicalpickles.com>
Body:
Date: Sat, 8 Aug 2009 11:42:06 -0400
From: Tester McTesty <test@test.com>
To: Josh Nichols <josh@technicalpickles.com>
Message-Id: <4a7d9cce149d7_53d158b421c1@technicalpickles.local.tmail>
Subject: blah
Mime-Version: 1.0
Content-Type: text/plain; charset=utf-8

* Message ends

Bug is NOT just on Ruby 1.9.1. I have the problem on Ruby 1.8.7. I assume anything that runs rails 2.3.3 will be unable to send email with a "Name" format.

This is a show stopper. Please release a new rails with this patch! The

I've added a fix in initializer for Rails 2.3.3 (fix_mailer_on_rails_2.3.3.rb):

module ActionMailer
  class Base
    def perform_delivery_smtp(mail)
      destinations = mail.destinations
      mail.ready_to_send
      sender = (mail['return-path'] && mail['return-path'].spec) || Array(mail.from).first

      smtp = Net::SMTP.new(smtp_settings[:address], smtp_settings[:port])
      smtp.enable_starttls_auto if smtp_settings[:enable_starttls_auto] && smtp.respond_to?(:enable_starttls_auto)
      smtp.start(smtp_settings[:domain], smtp_settings[:user_name], smtp_settings[:password],
                 smtp_settings[:authentication]) do |smtp|
        smtp.sendmail(mail.encoded, sender, destinations)
      end
    end
  end
end

Lets wait till the end of the month, when 2.3.4 will be released.

Thanks Dmitry. The initialiser was very helpful.

Why did this not get applied to rails 2.3.4? Seems like a no brainer. Thanks to Dmitry for a work around.

Ouch, still not patched? Why not in 2.3.4?

Just plowed head long into this issue using 2.3.4 and ruby 1.8. Is the patch in the queue for next release?

+1 from me. I just ran into this issue after upgrading from 2.2. I'm running ruby 1.8. For now, I'm using Dmitry's workaround, but it would be great to get this in the release.

1. I am also experiencing this issue. Dmitry Polushkin's workaround works for me.

Verified this is a still problem on 2.3.4.

Are there any issues with the attached patches? Would really like to see this fixed so I don't have to monkey patch ActionMailer in an initializer.

We're using the Patch by Joey A. successfully in production.

+1

#3078 ActionMailer 2.3.3 broke display name support in from address when using SMTP is a duplicate of this ticket

So this problem doesn't just happen with ruby 1.9? If so, the ticket title should be updated.

in response to Josh Nichol's Post:

Why on earth are emails being sent with multiple From/To lines?

nm. i imagine the paste is slightly different than actual output and one is MAIL FROM/RCPT TO, and other is just From/To.

Apologize.

I got this today on 1.8.6 on Engine Yard, on Rails 2.3.3 and 2.3.4 ....

It's a shame this didn't make it in to 2.3.4 ... seems like it's a pretty serious bug, and I can't imagine too many people using mailers that send with just an email address. It would essentially break any app that relied on named mailers that upgraded to 2.3.3 or 2.3.4.

Is 2.3.5 on the cards soon? Would something like this not warrant a small point release?

I agree with Paul. This bug is nasty. Our site was not sending emails for an hour after deploying. To make matters worse, exception notifier was broken too so we were not notified of the problem. This should be pushed out as a point release immediately. This kind of thing can do real damage to production apps.

Gabe, I had to go through the exact same. No registration emails, no exception notifications. This is by far the most critical issue I had with Rails so far. And it's a shame that nothing has happened such a long time.

+1, this is worth a point release by itself. This is a show stopper and it has been broken for months now. A real shame.

Please fix!

We should start a tweet blast or something to get some awareness

My another +1 for this ticket.

I had the same problem with ActionMailer 2.2.2 and Ruby 1.8.7-174 with Postfix.

A workaround is to add the following line to your notification methods:

from       "Me <noreply@mydomain.com>"

• headers "return-path" => 'noreply@mydomain.com' subject "Here is the Subject!"

Not sure if that works for the versions of ActionMailer and Ruby in question...

Oh barf, my first post and I mess up the formatting. The workaround looks like:

    from       "Symantec Health <noreply@symantechealth.com>"
+   headers    "return-path" => 'noreply@symantechealth.com'
    subject    "New Symantec Health Sales Lead!"

+1 for this ticket and for Dmitry's code.

+1 for this issue being seen in production and successful use of Dmitry's initializer code in Rails 2.3.4 with MRI Ruby 1.8.7.

The initializer from Dmitry Polushkin fixed my broken apps.

In case anybody's looking for them, the commits that fix this are da61a6c9 on 2-3-stable and 7e0aa35c on master.