Content-Transfer-Encoding e-mail header

RT Users
1

Hello all,

We are having a problem where e-mail is not being delivered to

addresses outside our domain. I have narrowed down the problem to the
e-mail headers that RT generates. But I am clueless as to why this is a
problem.

We are an all-Windows shop, except for one ubuntu 8.10 server that

runs RT 3.8 under Apache 2. For mail, it uses Postfix, and routes all
mail to our local Exchange server (Exchange 2003 under Windows Server
2000). For e-mail that RT sends to recipients inside our domain, it all
works well. But we have some contractors who need to receive e-mail
from RT on certain events, and these contractors have addresses outside
our network. But the mail is never delivered.

After much experimentation, I narrowed the problem down to the

“Content-Transfer-Encoding: 8bit” header. If that header is present,
e-mail does not get delivered outside our network (e.g. to gmail.com,
yahoo.com, anywhere); if that header is absent, e-mail goes through
fine.

syslog tells me nothing useful: No matter what, it reports "mail

queued for delivery", which I presume is coming from the Exchange
server.

Now, I know this is not an RT problem, because I reproduced the

problem consistently at the ubuntu command line by manually invoking
sendmail. But a) I wonder if that header is required by RT, or if an
alternative (base64?) could be used instead; and b) Maybe I’ll get lucky
and someone on the list will know a solution anyhow.

Thanks in advance,

Eric J. Roode
Senior Enterprise Developer
Barrack, Rodos & Bacine
(215) 963-0600

2

I think newer sendmails takes a -B option of 7BIT, or 8BITMIME. Check your sendmail man pages. Test it on the command line. Fix it by copying the sendmail lines from your RT_Config.om to your RT_SiteConfig.pm, and changing them there (and, then restarting apache…)From: rt-users-bounces@lists.bestpractical.com [mailto:rt-users-bounces@lists.bestpractical.com] On Behalf Of Roode, Eric
Sent: Thursday, October 01, 2009 1:36 PM
To: rt-users@lists.bestpractical.com
Subject: [rt-users] Content-Transfer-Encoding e-mail header

Hello all,

We are having a problem where e-mail is not being delivered to addresses outside our domain.  I have narrowed down the problem to the e-mail headers that RT generates.  But I am clueless as to why this is a problem.

We are an all-Windows shop, except for one ubuntu 8.10 server that runs RT 3.8 under Apache 2.  For mail, it uses Postfix, and routes all mail to our local Exchange server (Exchange 2003 under Windows Server 2000).  For e-mail that RT sends to recipients inside our domain, it all works well.  But we have some contractors who need to receive e-mail from RT on certain events, and these contractors have addresses outside our network.  But the mail is never delivered.

After much experimentation, I narrowed the problem down to the "Content-Transfer-Encoding: 8bit" header.  If that header is present, e-mail does not get delivered outside our network (e.g. to gmail.com, yahoo.com, anywhere); if that header is absent, e-mail goes through fine.

syslog tells me nothing useful: No matter what, it reports "mail queued for delivery", which I presume is coming from the Exchange server.

Now, I know this is not an RT problem, because I reproduced the problem consistently at the ubuntu command line by manually invoking sendmail.  But a) I wonder if that header is required by RT, or if an alternative (base64?) could be used instead; and b) Maybe I'll get lucky and someone on the list will know a solution anyhow.

Thanks in advance,

Eric J. Roode
Senior Enterprise Developer
Barrack, Rodos & Bacine
(215) 963-0600

This e-mail message is intended only for the personal use of the recipient(s) named above. If you are not an intended recipient, you may not review, copy or distribute this message. If you have received this communication in error, please notify the Hearst Service Center (cadmin@hearstsc.com) immediately by email and delete the original message.

3

I think newer sendmails takes a -B option of 7BIT, or 8BITMIME.
Check your sendmail man pages. Test it on the command line.
Fix it by copying the sendmail lines from your RT_Config.om to your
RT_SiteConfig.pm, and changing them there (and, then restarting
apache…)

Thanks for the tip. It didn’t seem to help. With -B 8BITMIME,
messages were delivered locally, but not out to the outside world,
whether Content-Transfer-Encoding was there or not. With
-B 7BIT, messages were delivered locally, but did not make it
to the outside world if the Content-Transfer-Encoding header
was present (i.e., the same behavior as before).

  • Eric
4

Got to thinking about this for a minute, and I think that Ubuntu actually uses exim, not sendmail - you can check by running sendmail -bV, which should give the version of sendmail (or exim) you are using…

If it is exim, it should be completely 8bit clean. So, someone in the middle is blocking it.

You might try not allowing rich text emails, by changing adding this to your RT_SiteConfig.pm

Set($MessageBoxRichText, 0);

At least, I think that’s what this will do! :)-----Original Message-----
From: rt-users-bounces@lists.bestpractical.com [mailto:rt-users-bounces@lists.bestpractical.com] On Behalf Of Roode, Eric
Sent: Thursday, October 01, 2009 2:20 PM
To: rt-users@lists.bestpractical.com
Subject: Re: [rt-users] Content-Transfer-Encoding e-mail header

From: Lander, Scott [mailto:slander@hearstsc.com]
Sent: Thursday, October 01, 2009 1:49 PM
To: Roode, Eric; rt-users@lists.bestpractical.com
Subject: RE: Content-Transfer-Encoding e-mail header

I think newer sendmails takes a -B option of 7BIT, or 8BITMIME.
Check your sendmail man pages. Test it on the command line.
Fix it by copying the sendmail lines from your RT_Config.om to your
RT_SiteConfig.pm, and changing them there (and, then restarting
apache…)

Thanks for the tip. It didn’t seem to help. With -B 8BITMIME,
messages were delivered locally, but not out to the outside world,
whether Content-Transfer-Encoding was there or not. With
-B 7BIT, messages were delivered locally, but did not make it
to the outside world if the Content-Transfer-Encoding header
was present (i.e., the same behavior as before).

  • Eric

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5

Got to thinking about this for a minute, and I think that Ubuntu actually uses exim, not sendmail - you can check by running sendmail -bV, which should give the version of sendmail (or exim) you are using…

IME Ubuntu uses postfix, which is actually what Eric said he was using…
(Postfix provides a wrapper called sendmail for compatability)

Cambridge Energy Alliance: Save money. Save the planet.

6

Hello all,

   We are having a problem where e-mail is not being delivered to addresses outside our

domain. I have narrowed down the problem to the e-mail headers that RT generates. But I am
clueless as to why this is a problem.

   We are an all-Windows shop, except for one ubuntu 8.10 server that runs RT 3.8 under

Apache 2. For mail, it uses Postfix, and routes all mail to our local Exchange server
(Exchange 2003 under Windows Server 2000). For e-mail that RT sends to recipients inside our
domain, it all works well. But we have some contractors who need to receive e-mail from RT on
certain events, and these contractors have addresses outside our network. But the mail is
never delivered.

   After much experimentation, I narrowed the problem down to the "Content-Transfer-Encoding:

8bit" header. If that header is present, e-mail does not get delivered outside our network
(e.g. to gmail.com, yahoo.com, anywhere); if that header is absent, e-mail goes through fine.

   syslog tells me nothing useful: No matter what, it reports "mail queued for delivery",

which I presume is coming from the Exchange server.

What do your exchange mail logs say?

7

OK - AFAIK, postfix.sendmail uses the -B 8BITMIME option.

But, there is also an option:
disable_mime_output_conversion=yes

Which might help…-----Original Message-----
From: Jerrad Pierce [mailto:jpierce@cambridgeenergyalliance.org]
Sent: Thursday, October 01, 2009 2:39 PM
To: Lander, Scott
Cc: Roode, Eric; rt-users@lists.bestpractical.com
Subject: Re: [rt-users] Content-Transfer-Encoding e-mail header

On Thu, Oct 1, 2009 at 14:35, Lander, Scott slander@hearstsc.com wrote:

Got to thinking about this for a minute, and I think that Ubuntu actually uses exim, not sendmail - you can check by running sendmail -bV, which should give the version of sendmail (or exim) you are using…

IME Ubuntu uses postfix, which is actually what Eric said he was using…
(Postfix provides a wrapper called sendmail for compatability)

Cambridge Energy Alliance: Save money. Save the planet.
This e-mail message is intended only for the personal use of the recipient(s) named above. If you are not an intended recipient, you may not review, copy or distribute this message. If you have received this communication in error, please notify the Hearst Service Center (cadmin@hearstsc.com) immediately by email and delete the original message.